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875-72-9

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875-72-9 Usage

General Description

2-methylideneadamantane, also known as rimantadine, is a chemical compound used as an antiviral medication. It belongs to the class of drugs known as adamantanes and is primarily used for the prevention and treatment of influenza A virus infections. The compound works by inhibiting the replication of the virus inside the host cells. It is a derivative of adamantane and contains a methylidene group on the 2 position of the molecule. Rimantadine is considered less effective than other antiviral drugs such as oseltamivir and zanamivir, and its use has decreased over the years due to the emergence of resistant strains of the virus. Despite this, it is still used in some countries and is considered to have a role in the management of influenza A infections.

Check Digit Verification of cas no

The CAS Registry Mumber 875-72-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,7 and 5 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 875-72:
(5*8)+(4*7)+(3*5)+(2*7)+(1*2)=99
99 % 10 = 9
So 875-72-9 is a valid CAS Registry Number.
InChI:InChI=1/C11H16/c1-7-10-3-8-2-9(5-10)6-11(7)4-8/h8-11H,1-6H2

875-72-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-methylideneadamantane

1.2 Other means of identification

Product number -
Other names 2-methylene adamantane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:875-72-9 SDS

875-72-9Synthetic route

2-Benzenesulfonylmethylene-adamantane

2-Benzenesulfonylmethylene-adamantane

2-methylideneadamantane
875-72-9

2-methylideneadamantane

Conditions
ConditionsYield
With ethanol; magnesium; mercury dichloride for 2h; Ambient temperature;99%
With ethanol; magnesium; mercury dichloride for 2h; Ambient temperature; other substrates;99%
2-methyladamantan-2-ol
702-98-7

2-methyladamantan-2-ol

2-methylideneadamantane
875-72-9

2-methylideneadamantane

Conditions
ConditionsYield
With potassium hydrogensulfate at 100℃; under 150 - 200 Torr;96%
With phosphoric acid85%
With toluene-4-sulfonic acid In toluene for 1h; Heating;65%
2-Adamantanone
700-58-3

2-Adamantanone

1-methyl-2-(methylsulfonyl)-1H-benzo[d]imidazole
61078-14-6

1-methyl-2-(methylsulfonyl)-1H-benzo[d]imidazole

2-methylideneadamantane
875-72-9

2-methylideneadamantane

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 1h; Reagent/catalyst; Temperature; Time; Inert atmosphere;96%
With sodium hexamethyldisilazane In N,N-dimethyl-formamide at -55 - 20℃; Reagent/catalyst; Temperature; Inert atmosphere;95%
2-Adamantanone
700-58-3

2-Adamantanone

methyllithium
917-54-4

methyllithium

2-methylideneadamantane
875-72-9

2-methylideneadamantane

Conditions
ConditionsYield
With thionyl chloride Product distribution; other alkyllithiums, other hindered ketones;94%
With thionyl chloride 1.) Et2O, -78 deg C, 30 min, 2.) a) -78 deg C, 5 min, b) RT, 30 min; Yield given. Multistep reaction;
2-Trimethylsilanylmethyl-adamantan-2-ol
58540-98-0

2-Trimethylsilanylmethyl-adamantan-2-ol

2-methylideneadamantane
875-72-9

2-methylideneadamantane

Conditions
ConditionsYield
Nafion-H In dichloromethane for 1h; Ambient temperature;88%
(i) nBuLi, THF, hexane, (ii) MeSO2Cl; Multistep reaction;
2-Adamantanone
700-58-3

2-Adamantanone

dichloromethane
75-09-2

dichloromethane

A

2-methylideneadamantane
875-72-9

2-methylideneadamantane

B

1-adamantanol
700-57-2

1-adamantanol

Conditions
ConditionsYield
With titanium tetrachloride; magnesium In tetrahydrofuran at 0 - 20℃; for 0.833333h;A 86%
B 6%
4(e)-Chloro-2-methyleneadamantane
74381-15-0

4(e)-Chloro-2-methyleneadamantane

2-methylideneadamantane
875-72-9

2-methylideneadamantane

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In cyclohexane for 20h; Heating;79.1%
2-bromo-2-methyladamantane
27852-61-5

2-bromo-2-methyladamantane

2-methylideneadamantane
875-72-9

2-methylideneadamantane

Conditions
ConditionsYield
With 2,4,6-triphenylverdazyl In acetonitrile for 48h; Ambient temperature;73%
In sulfolane at 30℃; Rate constant; Kinetics; Thermodynamic data; other temperatures; ΔH(excit.), ΔS(excit.); other aprotic solvents;
With 1,3,5-triphenylverdazyl In cyclohexanone at 25℃; Thermodynamic data; Kinetics; Further Variations:; Solvents;
2',5'-dihydrospiro
31934-34-6

2',5'-dihydrospiro

A

2-methylideneadamantane
875-72-9

2-methylideneadamantane

B

spiro
56169-89-2

spiro

C

homoadamantane-2-thione
97462-11-8

homoadamantane-2-thione

Conditions
ConditionsYield
In xylene at 80℃; for 30h;A 3%
B 70%
C 16%
In xyleneA 3 % Spectr.
B 63 % Spectr.
C 14 % Spectr.
In xylene at 80℃; for 30h; Product distribution; Rate constant; thermolysis in xylene, in benzyl alcohol or piperidine; kinetic of thermolysis in xylene; regiochemistry of cycloaddition of diazomethane to adamantanethione; kinetic of thermolysis of 2',5'-dihydrospiro;A 3 % Spectr.
B 64 % Spectr.
C 14 % Spectr.
C11H16N2S
31934-34-6

C11H16N2S

A

2-methylideneadamantane
875-72-9

2-methylideneadamantane

B

homoadamantane-2-thione
97462-11-8

homoadamantane-2-thione

C

C11H16S
56169-89-2

C11H16S

Conditions
ConditionsYield
In xylene at 80℃; for 30h;A 3%
B 16%
C 70%
2-Adamantanone
700-58-3

2-Adamantanone

1,2-dibromomethane
74-95-3

1,2-dibromomethane

2-methylideneadamantane
875-72-9

2-methylideneadamantane

Conditions
ConditionsYield
With titanium tetrachloride; zinc In tetrahydrofuran; dichloromethane at -40℃;66%
With titanium tetrachloride; zinc In tetrahydrofuran; dichloromethane Ambient temperature;
2-Adamantanone
700-58-3

2-Adamantanone

methyl-triphenylphosphonium iodide
2065-66-9

methyl-triphenylphosphonium iodide

2-methylideneadamantane
875-72-9

2-methylideneadamantane

Conditions
ConditionsYield
Stage #1: methyl-triphenylphosphonium iodide With n-butyllithium In tetrahydrofuran at 20℃; for 0.25h;
Stage #2: 2-Adamantanone In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;
66%
Stage #1: methyl-triphenylphosphonium iodide With n-butyllithium In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #2: 2-Adamantanone In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;
66%
1-(tert-butyl)-5-(methylsulfonyl)-1H-tetrazole
873869-19-3

1-(tert-butyl)-5-(methylsulfonyl)-1H-tetrazole

2-Adamantanone
700-58-3

2-Adamantanone

2-methylideneadamantane
875-72-9

2-methylideneadamantane

Conditions
ConditionsYield
With caesium carbonate In tetrahydrofuran; N,N-dimethyl-formamide at 70℃; for 16h;57%
2-Adamantanone
700-58-3

2-Adamantanone

Methylenetriphenylphosphorane
19493-09-5

Methylenetriphenylphosphorane

2-methylideneadamantane
875-72-9

2-methylideneadamantane

Conditions
ConditionsYield
In dimethyl sulfoxide at 56℃; for 2h;55%
2-Adamantanone
700-58-3

2-Adamantanone

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

2-methylideneadamantane
875-72-9

2-methylideneadamantane

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere;
Stage #2: 2-Adamantanone In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere;
50%
With phenyllithium 1.) ether, 30 min, 2.) 2 h; Yield given. Multistep reaction;
With n-butyllithium In diethyl ether; hexane 1.) 30 min, 2.) room temperature, 30 min; reflux 17 h;80 % Spectr.
ω-(Bromomethylene)adamantane
68251-94-5

ω-(Bromomethylene)adamantane

A

2-methylideneadamantane
875-72-9

2-methylideneadamantane

B

1,2-diadamantylideneethane
94052-77-4

1,2-diadamantylideneethane

Conditions
ConditionsYield
With lithium; copper(I) bromide In diethyl ether for 3h; Heating;A n/a
B 21%
2-Adamantanone
700-58-3

2-Adamantanone

methyl iodide
74-88-4

methyl iodide

2-methylideneadamantane
875-72-9

2-methylideneadamantane

Conditions
ConditionsYield
(i) Ph3P, (ii) nBuLi, (iii) /BRN= 1210235/; Multistep reaction;
methanol
67-56-1

methanol

2-bromo-2-methyladamantane
27852-61-5

2-bromo-2-methyladamantane

A

2-methylideneadamantane
875-72-9

2-methylideneadamantane

B

2-methyl-2-methoxyadamantane
51086-30-7

2-methyl-2-methoxyadamantane

Conditions
ConditionsYield
at 25℃; Rate constant; Mechanism; other proton-donating and aprotic solvents;
2-Adamantanone
700-58-3

2-Adamantanone

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

A

2-methylideneadamantane
875-72-9

2-methylideneadamantane

B

1-adamantanol
700-57-2

1-adamantanol

Conditions
ConditionsYield
With n-butyllithium In hexane; toluene Product distribution; Mechanism; 1.) 30 min, 2.) room temperature, 30 min; reflux, 17 h; other solvents, other reagents, time; other ketones;
2-Adamantanone
700-58-3

2-Adamantanone

2-methylideneadamantane
875-72-9

2-methylideneadamantane

Conditions
ConditionsYield
Wittig reaction conditions;
Multi-step reaction with 2 steps
1: diethyl ether / 18 h / Ambient temperature
2: 65 percent / p-toluenesulfonic acid / toluene / 1 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: diethyl ether; pentane / 0.17 h / 0 °C
2: 88 percent / Nafion-H / CH2Cl2 / 1 h / Ambient temperature
View Scheme
tert-Amyl alcohol
75-85-4

tert-Amyl alcohol

2-bromo-2-methyladamantane
27852-61-5

2-bromo-2-methyladamantane

A

2-methylideneadamantane
875-72-9

2-methylideneadamantane

B

2-(1,1-Dimethyl-propoxy)-2-methyl-adamantane

2-(1,1-Dimethyl-propoxy)-2-methyl-adamantane

Conditions
ConditionsYield
at 25℃; Rate constant;
ethanol
64-17-5

ethanol

2-bromo-2-methyladamantane
27852-61-5

2-bromo-2-methyladamantane

A

2-methylideneadamantane
875-72-9

2-methylideneadamantane

B

2-methyl-2-adamantanyl ethyl ether

2-methyl-2-adamantanyl ethyl ether

Conditions
ConditionsYield
at 25℃; Rate constant;
2-methyladamantan-2-ol
702-98-7

2-methyladamantan-2-ol

A

2-Adamantanone
700-58-3

2-Adamantanone

B

2-methyl-1-adamantanol
24557-02-6

2-methyl-1-adamantanol

C

2-methylideneadamantane
875-72-9

2-methylideneadamantane

D

E,Z-4-methyl-1-adamantanol
21365-85-5

E,Z-4-methyl-1-adamantanol

Conditions
ConditionsYield
With potassium hydroxide; nitric acid; trifluoroacetic acid 1) 65 deg C, 3.5 h, 2) 95 deg C, 2.5 h; Yield given. Multistep reaction. Yields of byproduct given;
2-bromo-2-methyladamantane
27852-61-5

2-bromo-2-methyladamantane

1,3,5-triphenylverdazyl
2154-65-6

1,3,5-triphenylverdazyl

A

2-methylideneadamantane
875-72-9

2-methylideneadamantane

B

2,4,6-triphenylverdazylium bromide
51940-11-5

2,4,6-triphenylverdazylium bromide

C

2,4,6-triphenylverdazyl
22459-57-0

2,4,6-triphenylverdazyl

Conditions
ConditionsYield
In acetonitrile at 25℃; Kinetics; Thermodynamic data; oth. solvents, effect of addition of var. salts, oth. temperature, ΔH(activ.), ΔS(activ.);
2-tert-butyl-2-adamantanol
38424-20-3

2-tert-butyl-2-adamantanol

A

2-methylideneadamantane
875-72-9

2-methylideneadamantane

B

2-isobutylidene-adamantane
13376-19-7

2-isobutylidene-adamantane

C

1-(2-adamantyl)-2-methylprop-1-ene
83782-92-7

1-(2-adamantyl)-2-methylprop-1-ene

Conditions
ConditionsYield
With hydrogenchloride In chloroform at 200℃; Heating; Further byproducts given;A 10 % Chromat.
B n/a
C n/a
With hydrogenchloride In chloroform at 150℃; for 48h; Product distribution; other reagent (HBr), reaction time, temperature;
2-bromo-2-methyladamantane
27852-61-5

2-bromo-2-methyladamantane

isopropyl alcohol
67-63-0

isopropyl alcohol

A

2-methylideneadamantane
875-72-9

2-methylideneadamantane

B

2-Isopropoxy-2-methyl-adamantane

2-Isopropoxy-2-methyl-adamantane

Conditions
ConditionsYield
at 25℃; Rate constant;
2-bromo-2-methyladamantane
27852-61-5

2-bromo-2-methyladamantane

A

2-methylideneadamantane
875-72-9

2-methylideneadamantane

B

2-sec-Butoxy-2-methyl-adamantane

2-sec-Butoxy-2-methyl-adamantane

Conditions
ConditionsYield
at 25℃; Rate constant;
2-bromo-2-methyladamantane
27852-61-5

2-bromo-2-methyladamantane

benzyl alcohol
100-51-6

benzyl alcohol

A

2-methylideneadamantane
875-72-9

2-methylideneadamantane

B

2-Benzyloxy-2-methyl-adamantane

2-Benzyloxy-2-methyl-adamantane

Conditions
ConditionsYield
at 25℃; Rate constant;
2-bromo-2-methyladamantane
27852-61-5

2-bromo-2-methyladamantane

tert-butyl alcohol
75-65-0

tert-butyl alcohol

A

2-methylideneadamantane
875-72-9

2-methylideneadamantane

B

2-tert-Butoxy-2-methyl-adamantane

2-tert-Butoxy-2-methyl-adamantane

Conditions
ConditionsYield
at 25℃; Rate constant;
2-bromo-2-methyladamantane
27852-61-5

2-bromo-2-methyladamantane

cyclohexanol
108-93-0

cyclohexanol

A

2-methylideneadamantane
875-72-9

2-methylideneadamantane

B

2-Cyclohexyloxy-2-methyl-adamantane

2-Cyclohexyloxy-2-methyl-adamantane

Conditions
ConditionsYield
at 25℃; Rate constant;
2-methylideneadamantane
875-72-9

2-methylideneadamantane

2-(Bromomethyl)-2-bromoadamantane
31482-53-8

2-(Bromomethyl)-2-bromoadamantane

Conditions
ConditionsYield
With bromine In dichloromethane Ambient temperature;99%
With bromine In tetrachloromethane Ambient temperature; overnight;82%
With bromine In tetrachloromethane
With bromine In tetrachloromethane at -15℃; Yield given;
With pyridine; bromine In pentane 1.) 1 h, 0 deg C; 2.) 2 h room temperature;18.2 g
trifluoromethyacrylic acid
381-98-6

trifluoromethyacrylic acid

2-methylideneadamantane
875-72-9

2-methylideneadamantane

2-trifluoromethyl-acrylic acid 2-methyl-adamantan-2-yl ester
188739-86-8

2-trifluoromethyl-acrylic acid 2-methyl-adamantan-2-yl ester

Conditions
ConditionsYield
With sodium hydroxide; sulfuric acid In toluene93%
2-methylideneadamantane
875-72-9

2-methylideneadamantane

bis(adamant-2-ylmethyl)phosphinic acid

bis(adamant-2-ylmethyl)phosphinic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; sodium hypophosphite In methanol; water at 120℃; for 10h; Sealed tube;92%
2-methylideneadamantane
875-72-9

2-methylideneadamantane

acrylic acid
79-10-7

acrylic acid

acrylic acid-2-methyl-2-adamantyl
249562-06-9

acrylic acid-2-methyl-2-adamantyl

Conditions
ConditionsYield
With sodium hydroxide; sulfuric acid In toluene91.5%
boron trifluoride diethyl etherate at 0℃; for 1h; Product distribution / selectivity;
poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

2-methylideneadamantane
875-72-9

2-methylideneadamantane

2-methyl-2-adamantyl methacrylate
177080-67-0

2-methyl-2-adamantyl methacrylate

Conditions
ConditionsYield
With sodium hydroxide; p-toluenesulfonic acid monohydrate In toluene90.8%
boron trifluoride diethyl etherate at 0℃; for 1h; Product distribution / selectivity;
boron trifluoride diethyl etherate In n-Undecane; toluene at 0℃; for 2h; Product distribution / selectivity;
boron trifluoride diethyl etherate In n-Undecane at 0℃; for 2h; Product distribution / selectivity;
2-methylideneadamantane
875-72-9

2-methylideneadamantane

1-benzyl-3-diazo-1,3-dihydro-2H-indol-2-one
461677-71-4

1-benzyl-3-diazo-1,3-dihydro-2H-indol-2-one

C26H27NO

C26H27NO

Conditions
ConditionsYield
dirhodium tetraacetate In dichloromethane at 20℃; for 0.166667h;89%
2-methylideneadamantane
875-72-9

2-methylideneadamantane

7-endo-carbomethoxybicyclo<3.3.1>nonan-3-one
87801-60-3

7-endo-carbomethoxybicyclo<3.3.1>nonan-3-one

Conditions
ConditionsYield
Stage #1: 2-methylideneadamantane With ferrous(II) sulfate heptahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ozone In methanol; water at -78 - 20℃; for 0.0833333h;
Stage #2: With magnesium bis(monoperoxyphthalate)hexahydrate In methanol; water at 0℃; for 2h;
87%
3-diazo-1-methyl-1,3-dihydro-indol-2-one
3265-14-3

3-diazo-1-methyl-1,3-dihydro-indol-2-one

2-methylideneadamantane
875-72-9

2-methylideneadamantane

C20H23NO

C20H23NO

Conditions
ConditionsYield
dirhodium tetraacetate In dichloromethane at 20℃; for 0.25h;85%
2-methylideneadamantane
875-72-9

2-methylideneadamantane

Trichloroacetyl chloride
76-02-8

Trichloroacetyl chloride

2’,2’-dichlorospiro[adamantane-2,3’-cyclobutane]-1‘-one
123489-40-7

2’,2’-dichlorospiro[adamantane-2,3’-cyclobutane]-1‘-one

Conditions
ConditionsYield
With triethylamine In hexane for 5h; Heating; also in ether with POCl3 and Zn as reagents;84%
With zinc In diethyl ether at 20 - 35℃; for 4h; Sonication;
With zinc In diethyl ether at 20 - 35℃; for 2h; Sonication;
2-methylideneadamantane
875-72-9

2-methylideneadamantane

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

diethyl (2-fluoroadamantan-2-yl)methylphosphonate
1454661-32-5

diethyl (2-fluoroadamantan-2-yl)methylphosphonate

Conditions
ConditionsYield
With silver nitrate; acetic acid; Selectfluor In dichloromethane; water at 40℃; for 18h; Schlenk technique; Inert atmosphere;81%
methanol
67-56-1

methanol

2-methylideneadamantane
875-72-9

2-methylideneadamantane

3β-Methoxycarbonyl-1α(H),5α(H)-bicyclo[3.3.1]nonan
19489-19-1

3β-Methoxycarbonyl-1α(H),5α(H)-bicyclo[3.3.1]nonan

Conditions
ConditionsYield
Stage #1: methanol; 2-methylideneadamantane With ozone
Stage #2: With ferrous(II) sulfate heptahydrate; thiophenol at -78 - 20℃; for 0.5h;
81%
1,1-bis[(triethylsilyl)dioxy]cyclohexane
960121-23-7

1,1-bis[(triethylsilyl)dioxy]cyclohexane

2-methylideneadamantane
875-72-9

2-methylideneadamantane

C17H26O2

C17H26O2

Conditions
ConditionsYield
With tin(IV) chloride In dichloromethane at -78 - -30℃;74%
2-methylideneadamantane
875-72-9

2-methylideneadamantane

1-allyl-3-diazo-1,3-dihydro-2H-indol-2-one
461677-72-5

1-allyl-3-diazo-1,3-dihydro-2H-indol-2-one

C22H25NO

C22H25NO

Conditions
ConditionsYield
dirhodium tetraacetate In dichloromethane at 20℃; for 0.2h;72%
2-methylideneadamantane
875-72-9

2-methylideneadamantane

4-[4-methoxy-4-(triethylsilylperoxy)cyclohexyl]phenyl acetate
1427281-56-8

4-[4-methoxy-4-(triethylsilylperoxy)cyclohexyl]phenyl acetate

cis-adamantane-2-spiro-3′-8′-(4′-acetoxyphenyl)-1′,2′-dioxaspiro[4.5]-decane

cis-adamantane-2-spiro-3′-8′-(4′-acetoxyphenyl)-1′,2′-dioxaspiro[4.5]-decane

Conditions
ConditionsYield
With tin(IV) chloride In dichloromethane at -78 - -30℃;70%
2-methylideneadamantane
875-72-9

2-methylideneadamantane

(PMePh2)2W(O)Cl2(CHCMe2Ph)

(PMePh2)2W(O)Cl2(CHCMe2Ph)

sodium 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-olate

sodium 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-olate

C31H27F18O3PW

C31H27F18O3PW

Conditions
ConditionsYield
Stage #1: (PMePh2)2W(O)Cl2(CHCMe2Ph); sodium 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-olate In toluene at 20℃; for 0.5h; Inert atmosphere;
Stage #2: 2-methylideneadamantane In toluene at 80℃; for 1h; Inert atmosphere; Sealed tube;
70%
2-methylideneadamantane
875-72-9

2-methylideneadamantane

1,3-cylohexanedione
504-02-9

1,3-cylohexanedione

C17H22O2

C17H22O2

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In methanol at 0℃;69%
4-phenyl-1,1-bis[(triethylsilyl)dioxy]cyclohexane
960121-27-1

4-phenyl-1,1-bis[(triethylsilyl)dioxy]cyclohexane

2-methylideneadamantane
875-72-9

2-methylideneadamantane

C23H30O2

C23H30O2

Conditions
ConditionsYield
With tin(IV) chloride In dichloromethane at -78 - -30℃;68%
2-methylideneadamantane
875-72-9

2-methylideneadamantane

dimedone
126-81-8

dimedone

C19H26O2

C19H26O2

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In methanol at 0℃;67%

875-72-9Relevant articles and documents

Worrell et al.

, p. 3525,3526,3528,3530,3531 (1974)

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Alford,J.R. et al.

, p. 880 - 883 (1971)

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Synthetic Photochemistry. LX. One-pot Formation of Spirocyclic 3-Acetyl-2-hydroxy-2-cyclopentenone Derivatives from Methylenecycloalkanes and Methyl 2,4-Dioxopentanoate

Hatsui, Toshihide,Ikeda, Shin-ya,Takeshita, Hitoshi

, p. 870 - 876 (1993)

A series of proto-photocycloadducts of methyl 2,4-dioxopentanoate to methylenecycloalkanes and -alkenes spontaneously caused retro-benzilic acid rearrangement in high yields.The results are utterly different from those of sterically-crowded acyclic alkenes, with which the rearrangement occurred by thermolysis as a minor process.

Energetics and Structure of the 1- and 2-Adamantyl Radicals and Their Corresponding Carbonium Ions by Photoelectron Spectroscopy

Kruppa, Gary H.,Beauchamp, J. L.

, p. 2162 - 2169 (1986)

The first photoelectron bands of the 1- and 2-adamantyl radicals, formed by flash vacuum photolysis of 1- and 2-adamantylmethyl nitrite, have been obtained.The adiabatic (IPa) and vertical (IPv) ionization potentials of the 1-adamantyl radical are 6.21 +/- 0.03 and 6.36 +/- 0.05 eV, respectively.IPa and IPv for the 2-adamantyl radical are 6.73 +/- 0.03 and 6.99 +/- 0.05 eV, respectively.The difference in hydride affinities between the 1-adamantyl and tert-butyl cations (Sharma, R.B.; Sen Sharma, D.K.; Hiraoka, K.; Kebarle, P.J.Am.Chem.Soc. 1985, 107, 3747) combined with the difference in IPa between the tert-butyl and 1-adamantyl radicals (0.49 +/- 0.06 eV) yield a value of 99 kcal/mol for the tertiary C-H bond energy in adamantane, 3.7 +/- 1.2 kcal/mol greater than the tertiary C-H bond energy in isobutane (assumed to be 95 kcal/mol).The effects of the geometrical constraints imposed by the adamantyl cage on the homolytic and heterolytic C-H-bond cleavage energies are disscussed for the 1- and 2-adamantyl cases.The width of the Franck-Condon envelope obtained is related to the geometry changes that occur upon ionization.The surprisingly broad envelope observed for the planar 2-adamantyl radical indicates that the Franck-Condon envelope for the 1-adamantyl radical should not be interpreted as exclusively due to changes at the bridgehead position.Thermal decomposition products of the 1- and 2-adamantyl radicals are observed, and the pathways for thermal decompositions of the radicals are discussed.To confirm expected trends in ionization potentials and band shapes or tertiary radicals, the first photoelectron band of the 2-methyl-2-butyl radical has been obtained.The IPa of the 2-methyl-2-butyl radical is 6.65 +/- 0.04 eV with IPv = 6.91 +/- 0.05 eV.

-

Hughes,L.,Ungold,K.U.,Walton,J.C.

, p. 7494 (1988)

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Oxo 2-Adamantylidene Complexes of Mo(VI) and W(VI)

Boudjelel, Maxime,Zhai, Feng,Schrock, Richard R.,Hoveyda, Amir H.,Tsay, Charlene

supporting information, p. 838 - 842 (2021/04/09)

Molybdenum and tungsten oxo 2-adamantylidene (Adene) complexes that contain two nonafluoro-tert-butoxide (ORF9) ligands have been prepared through addition of 2-methylene-or 2-ethylideneadamantane to neophylidene or neopentylidene complexes. The isolated oxo complexes include W(O)(Adene)(ORF9)2(PPh2Me) (1W), W(O)(Adene)(ORF9)2 (2W), W(O)(Adene)(2,5-dimethylpyrrolide)2 (3W), W(O)(Adene)(2,5-dimethylpyrrolide)(2,6-dimesitylphenoxide) (4W), Mo(O)(Adene)(ORF9)2(PPhMe2) (1Mo), and Mo(O)(Adene)(ORF9)2 (2Mo). Compound 2W is a dimer that contains unsymmetrically bridging oxo ligands; it dissociates readily and reversibly into monomers, especially in the presence of a donor such as THF. In contrast, 2Mo is a monomer. Both 2W and 2Mo are remarkably stable thermally. The pale-blue complexes Mo(Adene)(ORF9)2Cl2 (5Mo) and W(Adene)(ORF9)2Cl2 (5W) are formed upon addition of PCl5 to 2Mo and 2W, respectively. The oxo complexes are reactive olefin metathesis initiators, while 5Mo and 5W are relatively poor initiators. We ascribe the thermal stability of 2Mo and 2W to resistance of the 2-adamantylidene ligands to couple bimolecularly, to the absence of an α-hydrogen in the alkylidene, or both.

COMPOUNDS AND METHODS FOR IDO AND TDO MODULATION, AND INDICATIONS THEREFOR

-

, (2019/10/15)

Disclosed are compounds of Formula (I) and (Ia) or a pharmaceutically acceptable salt, a solvate, a tautomer, a stereoisomer or a deuterated analog thereof, wherein R4, R5, R6, and R7 are as described in any of the embodiments described in this disclosure; compositions thereof; and uses thereof.

COMPOUNDS AND METHODS FOR IDO AND TDO MODULATION, AND INDICATIONS THEREFOR

-

, (2018/04/20)

Disclosed are compounds of Formula I (a) or a pharmaceutically acceptable salt, a solvate, a tautomer, an isomer or a deuterated analog thereof, wherein R4, R5, R6, R7, G1, G2 and Ring A are as described in any of the embodiments described in this disclosure; compositions thereof; and uses thereof.

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