tributyl(trichloroacetoxy)stannane
cyclopenta-1,3-diene
A
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
B
tributyltin chloride
C
Triphenylphosphine oxide
Conditions | Yield |
---|---|
With triphenylphosphine | A 30% B 90% C 92% |
With P(C6H5)3 | A 30% B 90% C 92% |
dichloroacethyl chloride
cyclopenta-1,3-diene
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
Conditions | Yield |
---|---|
With triethylamine In pentane for 4h; Heating; | 88% |
With triethylamine In hexane; n-heptane at 20℃; | 86% |
With triethylamine In hexane at 20℃; | 85% |
β,β-dichloroacryloyl chloride
cyclopenta-1,3-diene
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
Conditions | Yield |
---|---|
With triethylamine In hexane at 26 - 30℃; for 9h; | 85% |
dichloroketene
cyclopenta-1,3-diene
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
Conditions | Yield |
---|---|
With triethylamine In pentane | 79% |
cyclopenta-1,3-diene
Trichloroacetyl chloride
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
Conditions | Yield |
---|---|
With zinc In diethyl ether at 0℃; for 1h; | 61% |
7,7-dichloro-2,4-exo-bis(trimethylsilyl)bicyclo<3.2.0>hept-2-en-6-one
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
Conditions | Yield |
---|---|
With sulfuric acid In methanol for 18h; Ambient temperature; | 37% |
trimethylsilyl trichloroacetate
cyclopenta-1,3-diene
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
Conditions | Yield |
---|---|
With triphenylphosphine |
5,5-bis(trimethylsilyl)cyclopentadiene
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 72 percent / triethylamine / hexane / 1.) ice-cooling, 2 h, 2.) 0 - 5 deg C, 12 h 2: 37 percent / conc. H2SO4 / methanol / 18 h / Ambient temperature View Scheme |
bi(cyclopentadiene)
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 200 °C 2: triethylamine / pentane View Scheme |
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Heating 2: triethylamine / n-heptane; hexane / 20 °C View Scheme |
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
7,7-dichloro-6-hydroxybicyclo<3.2.0>hept-2-ene
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol for 21h; Ambient temperature; | 96% |
With lithium aluminium tetrahydride In diethyl ether for 1h; Ambient temperature; |
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
7,7-dichloro-6-hydroxybicyclo<3.2.0>hept-2-ene-6-d
Conditions | Yield |
---|---|
With sodium borodeuteride In methanol for 15h; Ambient temperature; | 95% |
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
2-hydroxy-2,4,6-cycloheptatrien-1-one
Conditions | Yield |
---|---|
With acetic acid; sodium hydroxide | 95% |
With sodium hydroxide; acetic acid at 130℃; for 7h; Rearrangement; | 87% |
With hydrogenchloride; sodium hydroxide; acetic acid for 8h; pH=1; Heating; | 77% |
With sodium hydroxide; acetic acid for 8h; Heating; | 77% |
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
(R)-1-phenyl-ethyl-amine
2-(dichloromethyl)-N-[(1R)-1-phenylethyl]cyclopent-3-ene-1-carboxamide
Conditions | Yield |
---|---|
In benzene at 20℃; for 4h; | 95% |
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
bicyclo(3.2.0)hept-2-en-6-one
Conditions | Yield |
---|---|
With zinc In acetic acid at 70℃; for 0.666667h; | 94% |
With acetic acid; zinc at 70℃; for 48h; | 83% |
With zinc In acetic acid | 81% |
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
Conditions | Yield |
---|---|
at 120 - 130℃; for 6h; | 93% |
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
Conditions | Yield |
---|---|
Stage #1: (+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one With sodium tetrahydroborate Stage #2: With ozone In methanol; dichloromethane at -78℃; for 0.166667h; Stage #3: With thiourea In methanol; dichloromethane at -78 - 20℃; Further stages.; | 93% |
ethanol
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
(Z)-7,7-Dichloro-hepta-4,6-dienoic acid ethyl ester
Conditions | Yield |
---|---|
In benzene Irradiation; irradiation with a Hanovia 450W high-pressure mercury arc lamp; | 90% |
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
2-diethylamino-1,3,2-dioxaphosphorinane
Conditions | Yield |
---|---|
at 120 - 130℃; for 6h; | 87% |
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
sodium methylate
methyl 2-(dichloromethyl)cyclopent-3-ene-1-carboxylate
Conditions | Yield |
---|---|
In methanol at -5 - 0℃; for 2h; | 83% |
diisobutyl phosphite
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
(7,7-Dichloro-6-hydroxy-bicyclo[3.2.0]hept-2-en-6-yl)-phosphonic acid diisobutyl ester
Conditions | Yield |
---|---|
With triethylamine In benzene Ambient temperature; | 70% |
dibutyl hydrogen phosphite
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
(7,7-Dichloro-6-hydroxy-bicyclo[3.2.0]hept-2-en-6-yl)-phosphonic acid dibutyl ester
Conditions | Yield |
---|---|
With triethylamine In benzene Ambient temperature; | 70% |
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
7,7-dideuteriobicyclo<3.2.0>hept-2-en-6-one
Conditions | Yield |
---|---|
With deuteroacetic acid; zinc | 67% |
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
di-n-propyl phosphonate
(7,7-Dichloro-6-hydroxy-bicyclo[3.2.0]hept-2-en-6-yl)-phosphonic acid dipropyl ester
Conditions | Yield |
---|---|
With triethylamine In benzene Ambient temperature; | 67% |
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
(+/-)-endo-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-ol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 20℃; for 1.5h; | 65% |
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
Dimethyl phosphite
dimethyl 6-hydroxy-7,7-dichlorobicyclo<3.2.0>hept-2-en-6-ylphosphonate
Conditions | Yield |
---|---|
With triethylamine In benzene for 5h; Ambient temperature; other dialkyl phosphites; | 62% |
With triethylamine In benzene for 5h; Ambient temperature; | 62% |
2-methoxy-[1,3,2]dioxaphosphinane
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
Conditions | Yield |
---|---|
at 120 - 130℃; for 6h; | 61% |
diisopropyl hydrogenphosphonate
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
(7,7-Dichloro-6-hydroxy-bicyclo[3.2.0]hept-2-en-6-yl)-phosphonic acid diisopropyl ester
Conditions | Yield |
---|---|
With triethylamine In benzene Ambient temperature; | 60% |
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
phosphonic acid diethyl ester
(7,7-Dichloro-6-hydroxy-bicyclo[3.2.0]hept-2-en-6-yl)-phosphonic acid diethyl ester
Conditions | Yield |
---|---|
With triethylamine In benzene Ambient temperature; | 60% |
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
4-methyl-2-methoxy-1,3,2-dioxaphosphorinane
Conditions | Yield |
---|---|
at 120 - 130℃; for 6h; | 60% |
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
(+/-)-2-formylcyclopent-2-enecarboxylic acid
Conditions | Yield |
---|---|
With sodium hydroxide In water at 60℃; for 1h; Solvent; Temperature; Concentration; Green chemistry; | 59.4% |
Stage #1: (+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one With water; triethylamine In tert-butyl alcohol for 3h; Reflux; Solvolysis; Stage #2: With potassium carbonate In tert-butyl alcohol at 10℃; for 0.5h; | 52% |
With sodium hydrogencarbonate at 75℃; for 5h; Hydrolysis; |
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
Conditions | Yield |
---|---|
With dihydrogen peroxide; sodium hydroxide In methanol; water at -5 - 30℃; | 57% |
1,3,2-dioxaphosphinan-2-oxide
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
Conditions | Yield |
---|---|
With triethylamine In benzene for 12h; | 55% |
4-methyl-[1,3,2]dioxaphosphinane 2-oxide
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
Conditions | Yield |
---|---|
With triethylamine In benzene for 12h; | 55% |
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
(R)-1-phenyl-ethyl-amine
A
(3R,3aS,6aR)-3-hydroxy-2-[(1R)-1-phenylethyl]-3,3a,6,6a-tetrahydrocyclopenta[c]pyrrol-1(2H)-one
B
(3S,3aR,6aS)-3-hydroxy-2-[(1R)-1-phenylethyl]-3,3a,6,6a-tetrahydrocyclopenta[c]pyrrol-1(2H)-one
Conditions | Yield |
---|---|
Stage #1: (+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one; (R)-1-phenyl-ethyl-amine In benzene at 20℃; for 4h; Stage #2: With barium(II) oxide In water; acetonitrile for 20h; Reflux; | A 47% B 46% |
The Bicyclo[3.2.0]hept-2-en-6-one,7,7-dichloro-, with the CAS registry number 5307-99-3, is also known as Dichlorobicycloheptenone. Its EINECS registry number is 226-165-0. This chemical's molecular formula is C7H6Cl2O and molecular weight is 177.0279. What's more, its systematic name is called 7,7-Dichlorobicyclo[3.2.0]hept-2-en-6-one. Its appearance is clear brown liquid.
Physical properties about this chemical are: (1)ACD/LogP: 0.56; (2)#of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.56; (4)ACD/LogD (pH 7.4): 0.56; (5)ACD/BCF (pH 5.5): 1.56; (6)ACD/BCF (pH 7.4): 1.56; (7)ACD/KOC (pH 5.5): 47.86; (8)ACD/KOC (pH 7.4): 47.86; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 17.07 Å2; (13)Index of Refraction: 1.568; (14)Molar Refractivity: 40.02 cm3; (15)Molar Volume: 122.2 cm3; (16)Surface Tension: 43.6 dyne/cm; (17)Density: 1.44 g/cm3; (18)Flash Point: 114.1 °C; (19)Enthalpy of Vaporization: 51.32 kJ/mol; (20)Boiling Point: 274.8 °C at 760 mmHg; (21)Vapour Pressure: 0.0053 mmHg at 25 °C.
Preparation of Bicyclo[3.2.0]hept-2-en-6-one,7,7-dichloro-: this chemical can be prepared by Cyclopenta-1,3-diene and 3,3-Dichloro-acryloyl chloride.
This reaction needs reagent Et3N and solvent Hexane at teperature of 26–30 °C. The reaction time is 9 hours. The yield is 85%.
Uses of Bicyclo[3.2.0]hept-2-en-6-one,7,7-dichloro-: it is used to produce other chemicals. For example, it is used to produce Bicyclo[3.2.0]hept-2-en-6-one.
The reaction occurs with reagent Zn and solvent Acetic acid. The yield is 81%.
When you are dealing with this chemical, you should be very careful. This chemical is irritating to eyes, respiratory system and skin. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. And in case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1) SMILES: ClC1(Cl)C(=O)C2C/C=C\C12
(2) InChI: InChI=1/C7H6Cl2O/c8-7(9)5-3-1-2-4(5)6(7)10/h1,3-5H,2H2
(3) InChIKey: JBPBARAOHIDZPU-UHFFFAOYAS
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