Products

Refine

Country

Business Type

Certificate

Display

Hubei CuiRan Biotechnology Co., Ltd

Hubei CuiRan Biotechnology Co., Ltd is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine,Traditional Chinese Medicine)

Rotenone

Cas:83-79-4

Min.Order:10 Milligram

Negotiable

Type:Lab/Research institutions

inquiry

Dayang Chem (Hangzhou) Co.,Ltd.

As a leading manufacturer and supplier of chemicals in China, DayangChem not only supply popular chemicals, but also DayangChem's R&D center offer custom synthesis services. DayangChem can provide different quantities of custom synthesis ch

Rotenone Manufacturer/High quality/Best price/In stock

Cas:83-79-4

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

inquiry

Hangzhou Dingyan Chem Co., Ltd

Items Standard Result Appearance -- White solid Purity -- 99.09%

High purity 83-79-4 Rotenone

Cas:83-79-4

Min.Order:1 Gram

FOB Price: $100.0 / 500.0

Type:Trading Company

inquiry

Simagchem Corporation

Welcome to Simagchem, your partner in China as a premier supply of bulk specialty chemicals for industry and life science. We introduce experienced quality product and exceptional JIT service with instant market intelligence in China to benefit our

High quality Rotenone supplier in China

Cas:83-79-4

Min.Order:0 Metric Ton

Negotiable

Type:Manufacturers

inquiry

Kono Chem Co.,Ltd

Superiority kono chem is a leading manufacturer and supplier of chemicals in China. We develop ,produce and distribute high quality pharmaceuticals, intermediates, special chemicals and other fine chemicals. We could give you: 1.Best

Rotenone with best price and top quality

Cas:83-79-4

Min.Order:1 Kilogram

FOB Price: $800.0 / 1000.0

Type:Other

inquiry

Xi'an Quanao Biotech Co., Ltd.

Top quality insecticide Rotenone 98% Rotenone powder Derris Root Extract Professional Factory We has a complete production and operating system, with an annual output capacity of 2000 tons. It can produce variety of content and proportion of extrac

Top quality insecticide Rotenone 98% Rotenone powder Derris Root Extract

Cas:83-79-4

Min.Order:100 Kilogram

FOB Price: $255.0 / 259.0

Type:Manufacturers

inquiry

Ality Chemical Corporation

The above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi

Xi'an Xszo Chem Co., Ltd.

1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s

High Quality 95% Pesticides TC Rotenone 83-79-4 GLP Manufacturer

Cas:83-79-4

Min.Order:1 Gram

FOB Price: $0.1

Type:Manufacturers

inquiry

COLORCOM LTD.

Colorcom is a global leader in industrial chemical manufacturing and is continuously innovating and transforming to exceed client expectations and industry standards. Colorcom prides itself on superior customer and technical focus, while focusing on

Rotenone

Cas:83-79-4

Min.Order:1 Metric Ton

Negotiable

Type:Manufacturers

inquiry

Chemwill Asia Co., Ltd.

Our main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block

Derris extract

Cas:83-79-4

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

inquiry

Hebei Nengqian Chemical Import and Export Co., LTD

Our Advantage Rich Experience Our products are sold all over Europe,North&South America, Sino-East, Asia and pacific area as well as Africa,we establish long term. Quality service Company cooperates with research institutes. We strictly con

Rotenone 83-79-4

Cas:83-79-4

Min.Order:1 Kilogram

FOB Price: $15.0 / 50.0

Type:Trading Company

inquiry

Zhuozhou Wenxi import and Export Co., Ltd

WITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et

Pharmaceutical Grade CAS 83-79-4 with competitive price

Cas:83-79-4

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

inquiry

Hebei Sankai Chemical Technology Co., Ltd

1. Product advantages ♦ High purity, all above 98.5%, no impurities after the dissolution ♦ We will test each batch to ensure quality ♦ OEM and private brand services designed for free ♦ Various cap colors available &diam

ROTENONE CAS83-79-4

Cas:83-79-4

Min.Order:1 Kilogram

FOB Price: $7.0 / 10.0

Type:Trading Company

inquiry

Henan Sinotech Import&Export Corporation

AS No 83-79-4 Appearance White powder Specifications (COA) Purity: 98% minLoss on Drying: 5.0% max Formulations 98% TC, 4% EC, 2.5% EC

Rotenone

Cas:83-79-4

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Other

inquiry

Shanghai Upbio Tech Co.,Ltd

1.No Less 8 years exporting experience. Clients can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specialized

Qingdao Beluga Import and Export Co., LTD

Rotenone CAS:83-79-4 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermediates, ster

Rotenone CAS:83-79-4

Cas:83-79-4

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Shandong Hanjiang Chemical Co., Ltd.

Hello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai

Rotenone

Cas:83-79-4

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Henan Wentao Chemical Product Co., Ltd.

Henan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod

Afine Chemicals Limited

Our Services 1. New Molecules R&D 2. Own test center HPLC NMR GC LC-MS 3. API and Intermediates from China reputed manufacturers 4. Documents support COA MOA MSDS DMF open part Our advantages 1. Government awarded company. Top 100 enter

Rotenone

Cas:83-79-4

Min.Order:1 Kilogram

FOB Price: $1.0 / 100000.0

Type:Lab/Research institutions

inquiry

Rely Chemicals Ltd.

Best quality/price/service Professional manufacturing FAO Standards Appearance:white or grey white powder Package:Solid:50g,100g,200g,250g,400g,500g,1kg,10kg bag ,20kg, 25kg,40kg bag,50kg,600kg, 900kg; Aluminum Foil Bag,plastic bag, fiber bag,

agricultural insecticide biologibal pesticide Rotenone 98%TC 2.5%EC CAS No.:83-79-4

Cas:83-79-4

Min.Order:0 Metric Ton

Negotiable

Type:Trading Company

inquiry

Hangzhou J&H Chemical Co., Ltd.

J&H CHEM R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. J&H CHEM has some Manufacturing base in Jia

Rotenone

Cas:83-79-4

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Zibo Hangyu Biotechnology Development Co., Ltd

Zibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi

High quality Rotenone

Cas:83-79-4

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

inquiry

Shandong Zhimao New Materials Co., Ltd.

Rotenone is widely present in the root bark of plants. It is a highly specific substance in toxicology. It has strong touch killing and stomach poisoning effects on insects, especially the larva of butterfly butterfly, Diamondback moth and aphids. Ea

ROTENONE

Cas:83-79-4

Min.Order:25 Metric Ton

Negotiable

Type:Trading Company

inquiry

HANGZHOU YUNUO CHEMICAL CO.,LTD

Superior quality, moderate price & quick delivery. Appearance:white powder Storage:Stored in cool, dry and ventilation place; Away from fire and heat Package:25kg/drum, or as per your request. Application:Used as Pharmaceutical Intermediates Tr

Xiamen Jenny Chemical Technology Co., Ltd.

GMP standard, high purity, competitive price, in stock 1. Quick Response: within 6 hours after receiving your email. 2. Quality Guarantee: All products are strictly tested by our QC, confirmed by QA, and approved by a third-party lab in China, USA,

Rotenone

Cas:83-79-4

Min.Order:1 Milligram

Negotiable

Type:Trading Company

inquiry

Suzhou Health Chemicals Co., Ltd.

High quality,stable supply chain.Appearance:white/off-white or light yellow Storage:Store in cool and dry place, keep away from strong light and heat. Package:aluminum bottle,glass bottle,PTFE bottle,cardboard drum Application:This product can be use

Rotenone

Cas:83-79-4

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Hebei yanxi chemical co.,LTD.

Content: 20%,40%, 90% Chemical name: (1,2,12,12a-tetrahidro-2 -iso-propeny-8, 9-dimethoxy-[1]-benzopyrane-[3,4-b] -furo-[2,3-h]-[1]-benzopyran-6-OH)

ROTENONE

Cas:83-79-4

Min.Order:1 Kilogram

Negotiable

Type:Trading Company

inquiry

shanghai Tauto Biotech Co., Ltd

The quality is guaranteed. If you find the product is wrong compared with COA, we promise 100% refund or change product. COA and HPLC will be shipped out with goods. You can also inform your analysis method and we will follow your analysis me

Rotenone

Cas:83-79-4

Min.Order:0 Metric Ton

Negotiable

Type:Manufacturers

inquiry

Hubei Vanz Pharm Co.,Ltd

ISO/factory/goodqualityAppearance:off white Storage:Dry,cool place Package:drum Application:active pharmaceutical ingredients Transportation:by air/sea/express Port:shenzhen/shanghai

ROTENONE

Cas:83-79-4

Min.Order:0

Negotiable

Type:Manufacturers

inquiry

Wuxi TAA Chemical Industry Co.,LTD.

1.A strong technical force and advanced processing equipments. The quality of the products has been strictly inspected and all kinds of index have reached or exceeded domestic and international standards.2. Now we have established long-term stable re

Rotenone CAS 83-79-4

Cas:83-79-4

Min.Order:0

Negotiable

Type:Other

inquiry

Synthetic route

(6aS,12aS,5'R)-rotenone enol acetate
23355-70-6

(6aS,12aS,5'R)-rotenone enol acetate

rotenone
83-79-4

rotenone

Conditions
ConditionsYield
With hydrogenchloride In methanol for 2h; Heating;83%
(2R,6aS,12aS)-8-hydroxy-9-methoxy-2-(prop-1-en-2-yl)-1,2,12,12a- tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one
34487-52-0

(2R,6aS,12aS)-8-hydroxy-9-methoxy-2-(prop-1-en-2-yl)-1,2,12,12a- tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one

rotenone
83-79-4

rotenone

Conditions
ConditionsYield
In diethyl ether59%
2-((2R,6aS,12aS)-8,9-dimethoxy-1,2,6,6a,12,12a-hexahydrochromeno[3,4-b]furo[2,3-h]chromen-2-yl)propan-2-ol
30462-22-7

2-((2R,6aS,12aS)-8,9-dimethoxy-1,2,6,6a,12,12a-hexahydrochromeno[3,4-b]furo[2,3-h]chromen-2-yl)propan-2-ol

A

rotenone
83-79-4

rotenone

B

Isorotenone
549-22-4

Isorotenone

Conditions
ConditionsYield
With Burgess Reagent In toluene for 0.5h; Reflux;A 50%
B 13%
With Burgess Reagent In toluene for 0.5h; Inert atmosphere; Reflux;A 50%
B 13%
2-((2R,6aS,12aS)-8,9-dimethoxy-1,2,6,6a,12,12a-hexahydrochromeno[3,4-b]furo[2,3-h]chromen-2-yl)propan-2-ol
30462-22-7

2-((2R,6aS,12aS)-8,9-dimethoxy-1,2,6,6a,12,12a-hexahydrochromeno[3,4-b]furo[2,3-h]chromen-2-yl)propan-2-ol

rotenone
83-79-4

rotenone

Conditions
ConditionsYield
With pyridine; thionyl chloride at 0℃; for 0.5h;40%
(6aS,12aR,5'R)-(trans)-(+)-rotenone
123000-20-4

(6aS,12aR,5'R)-(trans)-(+)-rotenone

rotenone
83-79-4

rotenone

Conditions
ConditionsYield
With hydrogenchloride In methanol; chloroform for 2h;
(6aR,12aS,5'R)-rotenone
123000-19-1

(6aR,12aS,5'R)-rotenone

rotenone
83-79-4

rotenone

Conditions
ConditionsYield
With hydrogenchloride In methanol; chloroform
With hydrogenchloride In methanol; chloroform epimerisation;
12a-hydroxyrotenone
509-96-6

12a-hydroxyrotenone

rotenone
83-79-4

rotenone

Conditions
ConditionsYield
With acetic acid; zinc(II) chloride; zinc In water at 100℃; for 2.5h;20 mg
6a,12a-dehydrorotenone
3466-09-9

6a,12a-dehydrorotenone

rotenone
83-79-4

rotenone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 31 mg / diisobutyaluminium hydride / toluene; tetrahydrofuran / 1 h / -78 °C
2: aq. HCl / methanol; CHCl3 / 2 h
View Scheme
Multi-step reaction with 2 steps
1: di-isobutylaluminium hydride
2: hydrogen chloride / methanol; CHCl3 / epimerisation
View Scheme
(6aS,12aS,5′R)-rotenone-6′-norketone
15130-81-1

(6aS,12aS,5′R)-rotenone-6′-norketone

A

rotenone
83-79-4

rotenone

B

aqueous-alcoholic KOH-solution

aqueous-alcoholic KOH-solution

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 50 percent / conc. H2SO4 / 3 h / Heating
2: 1.) n-BuLi / 1.) THF, 35 deg C, 5 min, 2.) THF, 1 h
3: 83 percent / conc. HCl / methanol / 2 h / Heating
View Scheme
rotenone 6'-norketone enol acetate
23295-59-2, 23295-65-0

rotenone 6'-norketone enol acetate

A

rotenone
83-79-4

rotenone

B

aqueous-alcoholic KOH-solution

aqueous-alcoholic KOH-solution

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) n-BuLi / 1.) THF, 35 deg C, 5 min, 2.) THF, 1 h
2: 83 percent / conc. HCl / methanol / 2 h / Heating
View Scheme
C11H14F2O2

C11H14F2O2

rotenone
83-79-4

rotenone

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: sodium hydride / hexane; mineral oil; N,N-dimethyl-formamide / 0 - 20 °C
2.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C
3.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C
3.2: 1.5 h / -78 - -30 °C
4.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C
5.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
6.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
8.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
9.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
10.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
11.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
12.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
12.2: 1.5 h / 50 °C
13.1: pyridine; thionyl chloride / 0.5 h / 0 °C
View Scheme
C11H14F2O2

C11H14F2O2

A

rotenone
83-79-4

rotenone

B

Isorotenone
549-22-4

Isorotenone

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: sodium hydride / hexane; mineral oil; N,N-dimethyl-formamide / 0 - 20 °C
2.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C
3.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C
3.2: 1.5 h / -78 - -30 °C
4.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C
5.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
6.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
8.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
9.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
10.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
11.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
12.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
12.2: 1.5 h / 50 °C
13.1: Burgess Reagent / toluene / 0.5 h / Reflux
View Scheme
C11H13FO2

C11H13FO2

rotenone
83-79-4

rotenone

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C
2.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C
2.2: 1.5 h / -78 - -30 °C
3.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C
4.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
5.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
7.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
8.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
9.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
10.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
11.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
11.2: 1.5 h / 50 °C
12.1: pyridine; thionyl chloride / 0.5 h / 0 °C
View Scheme
C11H13FO2

C11H13FO2

A

rotenone
83-79-4

rotenone

B

Isorotenone
549-22-4

Isorotenone

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C
2.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C
2.2: 1.5 h / -78 - -30 °C
3.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C
4.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
5.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
7.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
8.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
9.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
10.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
11.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
11.2: 1.5 h / 50 °C
12.1: Burgess Reagent / toluene / 0.5 h / Reflux
View Scheme
C13H17FO3

C13H17FO3

rotenone
83-79-4

rotenone

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C
1.2: 1.5 h / -78 - -30 °C
2.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C
3.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
4.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
6.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
7.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
8.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
9.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
10.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
10.2: 1.5 h / 50 °C
11.1: pyridine; thionyl chloride / 0.5 h / 0 °C
View Scheme
C13H17FO3

C13H17FO3

A

rotenone
83-79-4

rotenone

B

Isorotenone
549-22-4

Isorotenone

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C
1.2: 1.5 h / -78 - -30 °C
2.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C
3.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
4.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
6.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
7.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
8.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
9.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
10.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
10.2: 1.5 h / 50 °C
11.1: Burgess Reagent / toluene / 0.5 h / Reflux
View Scheme
1,3-Difluorobenzene
372-18-9

1,3-Difluorobenzene

rotenone
83-79-4

rotenone

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 1.42 h / -78 °C
1.2: 2 h / 20 °C
2.1: potassium osmate; potassium hexacyanoferrate(III); potassium carbonate; methanesulfonamide; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane] / tert-butyl alcohol; water / 120 h / 0 - 20 °C
3.1: sodium hydride / hexane; mineral oil; N,N-dimethyl-formamide / 0 - 20 °C
4.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C
5.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C
5.2: 1.5 h / -78 - -30 °C
6.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C
7.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
8.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
10.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
11.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
12.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
13.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
14.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
14.2: 1.5 h / 50 °C
15.1: pyridine; thionyl chloride / 0.5 h / 0 °C
View Scheme
1,3-Difluorobenzene
372-18-9

1,3-Difluorobenzene

A

rotenone
83-79-4

rotenone

B

Isorotenone
549-22-4

Isorotenone

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 1.42 h / -78 °C
1.2: 2 h / 20 °C
2.1: potassium osmate; potassium hexacyanoferrate(III); potassium carbonate; methanesulfonamide; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane] / tert-butyl alcohol; water / 120 h / 0 - 20 °C
3.1: sodium hydride / hexane; mineral oil; N,N-dimethyl-formamide / 0 - 20 °C
4.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C
5.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C
5.2: 1.5 h / -78 - -30 °C
6.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C
7.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
8.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
10.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
11.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
12.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
13.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
14.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
14.2: 1.5 h / 50 °C
15.1: Burgess Reagent / toluene / 0.5 h / Reflux
View Scheme
C31H44F2O8Si

C31H44F2O8Si

rotenone
83-79-4

rotenone

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C
2.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
3.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
5.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
6.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
7.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
8.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
9.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
9.2: 1.5 h / 50 °C
10.1: pyridine; thionyl chloride / 0.5 h / 0 °C
View Scheme
C31H44F2O8Si

C31H44F2O8Si

A

rotenone
83-79-4

rotenone

B

Isorotenone
549-22-4

Isorotenone

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C
2.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
3.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
5.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
6.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
7.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
8.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
9.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
9.2: 1.5 h / 50 °C
10.1: Burgess Reagent / toluene / 0.5 h / Reflux
View Scheme
Multi-step reaction with 10 steps
1.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C / Inert atmosphere
1.2: 0.5 h / 20 °C / Inert atmosphere
2.1: pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C / Inert atmosphere
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
4.1: potassium tert-butylate; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine / toluene / 2 h / Inert atmosphere; Reflux
5.1: aluminum (III) chloride; lithium aluminium tetrahydride / diethyl ether; dichloromethane / 0.33 h / 0 °C / Inert atmosphere
6.1: sodium hydride; 15-crown-5; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / toluene / 2 h / 80 °C / Inert atmosphere
7.1: 10 wt% Pd(OH)2 on carbon; hydrogen / tetrahydrofuran; tert-butyl alcohol; water / 3 h / 20 °C
8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere
9.1: hydrogenchloride / methanol / 1.5 h / 50 °C / Inert atmosphere
10.1: Burgess Reagent / toluene / 0.5 h / Inert atmosphere; Reflux
View Scheme
C31H46F2O8Si

C31H46F2O8Si

rotenone
83-79-4

rotenone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
3.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
4.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
5.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
6.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
7.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
7.2: 1.5 h / 50 °C
8.1: pyridine; thionyl chloride / 0.5 h / 0 °C
View Scheme
C31H46F2O8Si

C31H46F2O8Si

A

rotenone
83-79-4

rotenone

B

Isorotenone
549-22-4

Isorotenone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
3.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
4.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
5.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
6.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
7.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
7.2: 1.5 h / 50 °C
8.1: Burgess Reagent / toluene / 0.5 h / Reflux
View Scheme
Multi-step reaction with 9 steps
1: pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C / Inert atmosphere
2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
3: potassium tert-butylate; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine / toluene / 2 h / Inert atmosphere; Reflux
4: aluminum (III) chloride; lithium aluminium tetrahydride / diethyl ether; dichloromethane / 0.33 h / 0 °C / Inert atmosphere
5: sodium hydride; 15-crown-5; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / toluene / 2 h / 80 °C / Inert atmosphere
6: 10 wt% Pd(OH)2 on carbon; hydrogen / tetrahydrofuran; tert-butyl alcohol; water / 3 h / 20 °C
7: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere
8: hydrogenchloride / methanol / 1.5 h / 50 °C / Inert atmosphere
9: Burgess Reagent / toluene / 0.5 h / Inert atmosphere; Reflux
View Scheme
C31H44F2O8Si

C31H44F2O8Si

rotenone
83-79-4

rotenone

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
2.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
4.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
5.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
6.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
7.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
8.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
8.2: 1.5 h / 50 °C
9.1: pyridine; thionyl chloride / 0.5 h / 0 °C
View Scheme
C31H44F2O8Si

C31H44F2O8Si

A

rotenone
83-79-4

rotenone

B

Isorotenone
549-22-4

Isorotenone

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
2.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
4.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
5.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
6.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
7.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
8.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
8.2: 1.5 h / 50 °C
9.1: Burgess Reagent / toluene / 0.5 h / Reflux
View Scheme
C39H52F2O9Si

C39H52F2O9Si

rotenone
83-79-4

rotenone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
2.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
3.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
4.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
5.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
6.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
6.2: 1.5 h / 50 °C
7.1: pyridine; thionyl chloride / 0.5 h / 0 °C
View Scheme
C39H52F2O9Si

C39H52F2O9Si

A

rotenone
83-79-4

rotenone

B

Isorotenone
549-22-4

Isorotenone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
2.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
3.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
4.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
5.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
6.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
6.2: 1.5 h / 50 °C
7.1: Burgess Reagent / toluene / 0.5 h / Reflux
View Scheme
Multi-step reaction with 8 steps
1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
2: potassium tert-butylate; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine / toluene / 2 h / Inert atmosphere; Reflux
3: aluminum (III) chloride; lithium aluminium tetrahydride / diethyl ether; dichloromethane / 0.33 h / 0 °C / Inert atmosphere
4: sodium hydride; 15-crown-5; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / toluene / 2 h / 80 °C / Inert atmosphere
5: 10 wt% Pd(OH)2 on carbon; hydrogen / tetrahydrofuran; tert-butyl alcohol; water / 3 h / 20 °C
6: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere
7: hydrogenchloride / methanol / 1.5 h / 50 °C / Inert atmosphere
8: Burgess Reagent / toluene / 0.5 h / Inert atmosphere; Reflux
View Scheme
C33H38F2O9

C33H38F2O9

rotenone
83-79-4

rotenone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
2.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
3.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
4.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
5.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
5.2: 1.5 h / 50 °C
6.1: pyridine; thionyl chloride / 0.5 h / 0 °C
View Scheme
C33H38F2O9

C33H38F2O9

A

rotenone
83-79-4

rotenone

B

Isorotenone
549-22-4

Isorotenone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
2.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
3.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
4.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
5.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
5.2: 1.5 h / 50 °C
6.1: Burgess Reagent / toluene / 0.5 h / Reflux
View Scheme
Multi-step reaction with 7 steps
1: potassium tert-butylate; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine / toluene / 2 h / Inert atmosphere; Reflux
2: aluminum (III) chloride; lithium aluminium tetrahydride / diethyl ether; dichloromethane / 0.33 h / 0 °C / Inert atmosphere
3: sodium hydride; 15-crown-5; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / toluene / 2 h / 80 °C / Inert atmosphere
4: 10 wt% Pd(OH)2 on carbon; hydrogen / tetrahydrofuran; tert-butyl alcohol; water / 3 h / 20 °C
5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere
6: hydrogenchloride / methanol / 1.5 h / 50 °C / Inert atmosphere
7: Burgess Reagent / toluene / 0.5 h / Inert atmosphere; Reflux
View Scheme
prenyl bromide
870-63-3

prenyl bromide

rotenone
83-79-4

rotenone

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 1.42 h / -78 °C
1.2: 2 h / 20 °C
2.1: potassium osmate; potassium hexacyanoferrate(III); potassium carbonate; methanesulfonamide; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane] / tert-butyl alcohol; water / 120 h / 0 - 20 °C
3.1: sodium hydride / hexane; mineral oil; N,N-dimethyl-formamide / 0 - 20 °C
4.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C
5.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C
5.2: 1.5 h / -78 - -30 °C
6.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C
7.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
8.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
10.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
11.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
12.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
13.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
14.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
14.2: 1.5 h / 50 °C
15.1: pyridine; thionyl chloride / 0.5 h / 0 °C
View Scheme
rotenone
83-79-4

rotenone

2R,6aS,12aS-2-isopropyl-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one
6659-45-6

2R,6aS,12aS-2-isopropyl-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In dichloromethane at 20℃;98%
With hydrogen; palladium on activated charcoal In ethyl acetate Ambient temperature;94%
With hydrogen; palladium on activated charcoal In acetone90%
rotenone
83-79-4

rotenone

(2R,6aR,12aS)-8,9-dimethoxy-2(prop-1-en-2-yl)-1,2,6,6a,12,12a- hexahydrochromeno[3,4-b]furo[2,3-h]chromen-6-ol

(2R,6aR,12aS)-8,9-dimethoxy-2(prop-1-en-2-yl)-1,2,6,6a,12,12a- hexahydrochromeno[3,4-b]furo[2,3-h]chromen-6-ol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 50℃; for 2h;98%
With sodium tetrahydroborate In methanol at 0℃; for 3h;95%
Multi-step reaction with 2 steps
1: two-dimensional iron(II) coordination polymer based on a divergent 4'-(4-diphenylamino)phenyl-4,2';6',4''-terpyridine ligand; potassium tert-butylate / tetrahydrofuran / 4 h / 20 °C / Green chemistry
2: silica gel / ethyl acetate; hexane / 20 °C
View Scheme
With sodium tetrahydroborate In methanol at 0 - 20℃; for 2h;
S-(trifluoromethyl)thianthrenium triflate

S-(trifluoromethyl)thianthrenium triflate

rotenone
83-79-4

rotenone

C24H23F3O6

C24H23F3O6

Conditions
ConditionsYield
With caesium carbonate; Benzene-1,2-dithiol In 1,4-dioxane at 10℃; for 7h; Inert atmosphere; Glovebox;96%
rotenone
83-79-4

rotenone

(6aS,12S,12aR,5′R)-12-deoxo-12-hydroxyrotenone
88390-15-2

(6aS,12S,12aR,5′R)-12-deoxo-12-hydroxyrotenone

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 20℃; for 2h; Inert atmosphere;92%
With sodium tetrahydroborate In methanol85%
With lithium aluminium tetrahydride Reduction;
With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Reduction; Heating;
trifluoromethane sulfonyl chloride
421-83-0

trifluoromethane sulfonyl chloride

rotenone
83-79-4

rotenone

(2R,6aS,12aS)-2-(2-chloro-4,4,4-trifluorobutan-2-yl)-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one

(2R,6aS,12aS)-2-(2-chloro-4,4,4-trifluorobutan-2-yl)-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; tris(1,10-phenanthroline)ruthenium(II) dichloride In dichloromethane at 25℃; for 15h; Inert atmosphere; Irradiation; regioselective reaction;92%
With dipotassium hydrogenphosphate; tris(1,10-phenanthroline)ruthenium(II) dichloride In dichloromethane at 25℃; for 15h; Photolysis; regioselective reaction;92%
With 2,4,6-trimethyl-pyridine; [Hf6(μ3-O)4(mu3-OH)4(formato)5.9(eosinato Y)0.1(4'-(4-carboxylatophenyl)[2,2':6',2''-terpyridine]-5,5''-dicarboxylato-Fe(OTf)2)2] In acetonitrile at 20℃; for 2h; Catalytic behavior; Inert atmosphere; Schlenk technique; Irradiation;70%
rotenone
83-79-4

rotenone

(2R,6aR,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one oxime
3276-14-0, 112838-10-5, 112838-11-6, 112838-12-7

(2R,6aR,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In ethanol for 10h; Reflux;91%
With hydroxylamine hydrochloride; sodium acetate In ethanol for 18h; Reflux;74%
With pyridine; hydroxylamine hydrochloride70%
With hydroxylamine
rotenone
83-79-4

rotenone

((2R,6aR,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-ylidene)hydrazine

((2R,6aR,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-ylidene)hydrazine

Conditions
ConditionsYield
With sodium acetate; hydrazine hydrate In ethanol at 80℃; for 5h;91%
6-(trimethylsilyl)hex-5-yn-1-yl 2-cyano-2-diazoacetate
1361382-43-5

6-(trimethylsilyl)hex-5-yn-1-yl 2-cyano-2-diazoacetate

rotenone
83-79-4

rotenone

C35H39NO8Si

C35H39NO8Si

Conditions
ConditionsYield
With Rh2(esp)2 In dichloromethane at 22℃; for 4h; Inert atmosphere; diastereoselective reaction;88%
rotenone
83-79-4

rotenone

(R)-5-(7,8-Dimethoxy-3,3a,4,9b-tetrahydro-chromeno[3,4-c]pyrazol-1-yl)-2-isopropenyl-2,3-dihydro-benzofuran-4-ol

(R)-5-(7,8-Dimethoxy-3,3a,4,9b-tetrahydro-chromeno[3,4-c]pyrazol-1-yl)-2-isopropenyl-2,3-dihydro-benzofuran-4-ol

Conditions
ConditionsYield
With potassium hydroxide; hydrazine In ethanol Heating;87%
With hydrazine hydrate In ethanol
rotenone
83-79-4

rotenone

(6aS,12aS,5’R)-rotenone hydrobromide
58277-58-0

(6aS,12aS,5’R)-rotenone hydrobromide

Conditions
ConditionsYield
With hydrogen bromide; acetic acid at 20℃; for 0.5h;87%
1,2-propanediene
463-49-0

1,2-propanediene

rotenone
83-79-4

rotenone

C26H28O6

C26H28O6

Conditions
ConditionsYield
Stage #1: rotenone With copper diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In tetrahydrofuran for 0.0833333h; Inert atmosphere;
Stage #2: 1,2-propanediene With (dimethoxy)methylsilane In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; diastereoselective reaction;
86%
phenylhydrazine
100-63-0

phenylhydrazine

rotenone
83-79-4

rotenone

(R)-5-(7,8-Dimethoxy-3-phenyl-3,3a,4,9b-tetrahydro-chromeno[3,4-c]pyrazol-1-yl)-2-isopropenyl-2,3-dihydro-benzofuran-4-ol

(R)-5-(7,8-Dimethoxy-3-phenyl-3,3a,4,9b-tetrahydro-chromeno[3,4-c]pyrazol-1-yl)-2-isopropenyl-2,3-dihydro-benzofuran-4-ol

Conditions
ConditionsYield
With potassium hydroxide In ethanol Heating;85%
rotenone
83-79-4

rotenone

2-((2R,6aS,12aS)-8,9-dimethoxy-1,2,6,6a,12,12a-hexahydrochromeno[3,4-b]furo[2,3-h]chromen-2-yl)propan-2-ol
30462-22-7

2-((2R,6aS,12aS)-8,9-dimethoxy-1,2,6,6a,12,12a-hexahydrochromeno[3,4-b]furo[2,3-h]chromen-2-yl)propan-2-ol

Conditions
ConditionsYield
With iron(III)-acetylacetonate; methyl 4-nitrobenzenesulfonate; phenylsilane; sodium hydrogencarbonate In methanol at 0 - 20℃; for 12h; Schlenk technique; Inert atmosphere; regioselective reaction;85%
Stage #1: rotenone With mercury(II) diacetate In tetrahydrofuran; water at 20℃; for 18h;
Stage #2: With sodium tetrahydroborate; sodium hydrogencarbonate In tetrahydrofuran; water
48%
With sodium tetrahydroborate; mercury(II) diacetate 1) H2O, THF, 20 deg C, 10 h, 2) 30 s; Yield given. Multistep reaction;
Multi-step reaction with 3 steps
1: 1) H2, pyridine / 1) 5percent Pd-BaSO4
2: 0.37 g / m-chloroperbenzoic acid, NaHCO3 / CH2Cl2; H2O / 0.75 h / 19 °C
3: 66 percent / activated Zn-dust / methanol / Ambient temperature
View Scheme
rotenone
83-79-4

rotenone

6aS,12aS-8,9-dimethoxy-2-(2-methyloxiran-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one
811451-63-5

6aS,12aS-8,9-dimethoxy-2-(2-methyloxiran-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 2h;85%
methylhydrazine
60-34-4

methylhydrazine

rotenone
83-79-4

rotenone

(R)-5-(7,8-Dimethoxy-3-methyl-3,3a,4,9b-tetrahydro-chromeno[3,4-c]pyrazol-1-yl)-2-isopropenyl-2,3-dihydro-benzofuran-4-ol

(R)-5-(7,8-Dimethoxy-3-methyl-3,3a,4,9b-tetrahydro-chromeno[3,4-c]pyrazol-1-yl)-2-isopropenyl-2,3-dihydro-benzofuran-4-ol

Conditions
ConditionsYield
With potassium hydroxide In ethanol Heating;84%
rotenone
83-79-4

rotenone

(6aS,12aS,5′R)-rotenone-6′-norketone
15130-81-1

(6aS,12aS,5′R)-rotenone-6′-norketone

Conditions
ConditionsYield
With sodium periodate; osmium(VIII) oxide In tetrahydrofuran; water; tert-butyl alcohol82%
With sodium periodate; osmium(VIII) oxide46%
rotenone
83-79-4

rotenone

12a-hydroxyrotenone
509-96-6

12a-hydroxyrotenone

Conditions
ConditionsYield
With potassium dichromate; acetic acid In water at 20 - 60℃; for 18.5h;82%
With dichromate anion; acetic acid51%
rotenone
83-79-4

rotenone

(2R,6S,6aS,12aS,2'R,6'S,6'aS,12'aS)-2,2'-Diisopropenyl-8,9,8',9'-tetramethoxy-1,2,12,12a,1',2',12',12'a-octahydro-6aH,6'aH-[6,6']bi[chromeno[3,4-b]furo[2,3-h]chromenyl]-6,6'-diol
82481-44-5

(2R,6S,6aS,12aS,2'R,6'S,6'aS,12'aS)-2,2'-Diisopropenyl-8,9,8',9'-tetramethoxy-1,2,12,12a,1',2',12',12'a-octahydro-6aH,6'aH-[6,6']bi[chromeno[3,4-b]furo[2,3-h]chromenyl]-6,6'-diol

Conditions
ConditionsYield
In acetic acid; acetonitrile electrochemical reduction;80%
In acetic acid; acetonitrile Product distribution; Mechanism; electrochemical reduction; variation of solvent;80 % Chromat.
rotenone
83-79-4

rotenone

(6aS,12S,12aR,5′R)-6′,7′-dihydro-12-deoxo-12-hydroxyamorphigenin

(6aS,12S,12aR,5′R)-6′,7′-dihydro-12-deoxo-12-hydroxyamorphigenin

Conditions
ConditionsYield
Stage #1: rotenone With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 1.5h; Inert atmosphere;
Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 18h;
80%
Stage #1: rotenone With borane In tetrahydrofuran Reduction; hydroboration;
Stage #2: With sodium hydroxide; dihydrogen peroxide Oxidation;
rotenone
83-79-4

rotenone

rotenol
3276-12-8

rotenol

Conditions
ConditionsYield
In water; acetonitrile electrochemical reduction;75%
With sodium hydroxide In ethanol Mechanism; Electrochemical reduction; tetrabutylammonium perchlorate, aqueous or aprotic medium;70%
With sodium hydroxide In ethanol controlled potential electrolysis, tetrabutylammonium perchlorate; other solvent DMF;70%
ethylamine
75-04-7

ethylamine

rotenone
83-79-4

rotenone

<1-(4-hydroxy-2-methylethenyl-2,3-dihydrobenzofuran-5-yl)-1-(6,7-dimethoxy-2H-chromen-4-yl)methylidene>ethylamine

<1-(4-hydroxy-2-methylethenyl-2,3-dihydrobenzofuran-5-yl)-1-(6,7-dimethoxy-2H-chromen-4-yl)methylidene>ethylamine

Conditions
ConditionsYield
In ethanol Product distribution; Heating; other amines, also with nitrenonone;73%
In ethanol Heating;73%
2-hydroxyethylhydrazine
109-84-2

2-hydroxyethylhydrazine

rotenone
83-79-4

rotenone

(R)-5-[3-(2-Hydroxy-ethyl)-7,8-dimethoxy-3,3a,4,9b-tetrahydro-chromeno[3,4-c]pyrazol-1-yl]-2-isopropenyl-2,3-dihydro-benzofuran-4-ol

(R)-5-[3-(2-Hydroxy-ethyl)-7,8-dimethoxy-3,3a,4,9b-tetrahydro-chromeno[3,4-c]pyrazol-1-yl]-2-isopropenyl-2,3-dihydro-benzofuran-4-ol

Conditions
ConditionsYield
With potassium hydroxide In ethanol Heating;71%
dimethylsulfoxonium methylide
70775-39-2, 5367-24-8

dimethylsulfoxonium methylide

rotenone
83-79-4

rotenone

6a,12a-methanorotenol

6a,12a-methanorotenol

Conditions
ConditionsYield
In tetrahydrofuran 1.) room temperature, 10 min, 2.) 45-55 deg C, 50 min;71%
(Difluoromethyl)triphenylphosphonium bromide
58310-28-4

(Difluoromethyl)triphenylphosphonium bromide

rotenone
83-79-4

rotenone

(2R,6aS,12aS)-2-(2-bromo-4,4-difluorobutan-2-yl)-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one

(2R,6aS,12aS)-2-(2-bromo-4,4-difluorobutan-2-yl)-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one

Conditions
ConditionsYield
With tris[2-phenylpyridinato-C2,N]iridium(III); copper(ll) bromide In N,N-dimethyl-formamide at 20℃; for 10h; Schlenk technique; Inert atmosphere; Irradiation;71%
N-4-methylphenylhydrazine
539-44-6

N-4-methylphenylhydrazine

rotenone
83-79-4

rotenone

(R)-5-(7,8-Dimethoxy-3-p-tolyl-3,3a,4,9b-tetrahydro-chromeno[3,4-c]pyrazol-1-yl)-2-isopropenyl-2,3-dihydro-benzofuran-4-ol

(R)-5-(7,8-Dimethoxy-3-p-tolyl-3,3a,4,9b-tetrahydro-chromeno[3,4-c]pyrazol-1-yl)-2-isopropenyl-2,3-dihydro-benzofuran-4-ol

Conditions
ConditionsYield
With potassium hydroxide In ethanol Heating;70%
methyl iodide
74-88-4

methyl iodide

rotenone
83-79-4

rotenone

(6aS,12aR,5'R)-/(6aR,12aS,5'R)-12a-methylrotenone
59456-14-3, 143838-84-0, 143838-90-8, 149116-35-8

(6aS,12aR,5'R)-/(6aR,12aS,5'R)-12a-methylrotenone

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h;66%
rotenone
83-79-4

rotenone

1-(4-hydroxy-2-methylethenyl-2,3-dihydrobenzofuran-5-yl)-7,8-dimethoxy-1,9b,3a,4-tetrahydro-2H-<1>-benzopyrano<4,3-d>isoxazol-1-ene

1-(4-hydroxy-2-methylethenyl-2,3-dihydrobenzofuran-5-yl)-7,8-dimethoxy-1,9b,3a,4-tetrahydro-2H-<1>-benzopyrano<4,3-d>isoxazol-1-ene

Conditions
ConditionsYield
With potassium hydroxide; hydroxylamine hydrochloride In ethanol for 3.5h; Heating;66%
dibromodifluoromethane
75-61-6

dibromodifluoromethane

rotenone
83-79-4

rotenone

(2R,6aS,12aS)-2-((R)-4-bromo-4,4-difluorobutan-2-yl)-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]-chromen-6(6aH)-one

(2R,6aS,12aS)-2-((R)-4-bromo-4,4-difluorobutan-2-yl)-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]-chromen-6(6aH)-one

Conditions
ConditionsYield
Stage #1: dibromodifluoromethane; rotenone With tetrahydrofuran; eosin at 20℃; for 5h; Irradiation; Inert atmosphere; Schlenk technique;
Stage #2: With potassium hydrogencarbonate for 5h; Inert atmosphere; Irradiation; Cooling with ice; Schlenk technique;
65%
dibromodifluoromethane
75-61-6

dibromodifluoromethane

rotenone
83-79-4

rotenone

C24H23BrF2O6

C24H23BrF2O6

Conditions
ConditionsYield
With eosin y In tetrahydrofuran at 20℃; for 10h; Inert atmosphere;65%

Raw Materials

Post buying leads

About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia

Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog

©2008 LookChem.com,License: ICP

NO.:Zhejiang16009103

complaints:service@lookchem.com Desktop View