maleic anhydride
cyclopenta-1,3-diene
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
Conditions | Yield |
---|---|
With 3-(n-butoxycarbonyl)-1-methylpyridinium bis(trifluoromethanesulfonyl)imide at 20℃; for 0.166667h; Diels-Alder reaction; diastereoselective reaction; | 100% |
With 1-hexyl-3-methylimidazolium tetrafluoroborate; K-10 montmorillonite at 20℃; for 0.0833333h; Diels-Alder reaction; | 99% |
In dichloromethane at 0 - 20℃; for 10h; Diels-Alder Cycloaddition; Inert atmosphere; | 98% |
bicyclo<2.2.1>-5-hepten-2endo,3endo-dicarboxylic anhydride
A
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
B
(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
Conditions | Yield |
---|---|
With sodium hydroxide In water at 70℃; for 0.166667h; Product distribution / selectivity; | A n/a B 87% |
With sodium hydroxide In water at 70℃; for 0.166667h; Product distribution / selectivity; | A 83% B 26% |
With sodium hydroxide In water at 70℃; for 0.166667h; Product distribution / selectivity; | A n/a B 50% |
A
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
B
(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
Conditions | Yield |
---|---|
Stage #1: cis-5-norbornene-endo-2,3-carboxycylic acid disodium salt With hydrogenchloride In water at 5 - 70℃; for 3.16667h; Stage #2: With acetic anhydride at 5 - 70℃; for 3.16667h; Product distribution / selectivity; | A n/a B 85% |
maleic anhydride
bi(cyclopentadiene)
A
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
B
(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
Conditions | Yield |
---|---|
at 206℃; for 0.366667h; Diels-Alder reaction; Neat (no solvent); | A 35% B 37% |
at 206℃; for 0.166667h; Diels-Alder reaction; Neat (no solvent); optical yield given as %de; |
3,4-Bis(trimethylsiloxy)-endo-tricyclo(4.2.1.02,5and)nona-3,7-dien
(1α,1'α',2α,2'α',5α,5'α',6α,6'α')-4,4'-Bis(trimethylsilyloxy)-4,4'-bi(tricyclo<4.2.1.02,5>non-7-enyl)-3,3'-dion
B
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
Conditions | Yield |
---|---|
With copper diacetate In acetic acid for 3h; Heating; | A 13% B 23% |
norbornene-5,6-dicarboxylic acid
A
(2E)-but-2-enedioic acid
B
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
Conditions | Yield |
---|---|
zuletzt Erhitzen unter 15 Torr; |
(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
Conditions | Yield |
---|---|
at 190℃; Gleichgewichtsgemisch; |
maleic anhydride
cyclopentene
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
Conditions | Yield |
---|---|
In diethyl ether |
(1R,2S,3R,4S)-3-Propylcarbamoyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
A
propylamine
B
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
Conditions | Yield |
---|---|
With water at 38℃; Rate constant; |
(1R,2S,3R,4S)-3-(2-Fluoro-ethylcarbamoyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
A
2-fluoroethylamine
B
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
Conditions | Yield |
---|---|
With water at 38℃; Rate constant; |
(1R,2S,3R,4S)-3-(2-Methoxy-ethylcarbamoyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
A
2-methoxyethylamine
B
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
Conditions | Yield |
---|---|
With water at 38℃; Rate constant; |
(1R,2S,3R,4S)-3-(2,2-Difluoro-ethylcarbamoyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
A
2,2-difluorethylamine
B
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
Conditions | Yield |
---|---|
With water at 38℃; Rate constant; |
(1R,2S,3R,4S)-3-(2,2,2-Trifluoro-ethylcarbamoyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
A
trifluoroethylamine
B
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
Conditions | Yield |
---|---|
With water at 38℃; Rate constant; |
Conditions | Yield |
---|---|
With water at 38℃; Rate constant; |
Conditions | Yield |
---|---|
With water at 38℃; Rate constant; |
Conditions | Yield |
---|---|
With water at 38℃; Rate constant; |
Conditions | Yield |
---|---|
With water at 38℃; Rate constant; |
Conditions | Yield |
---|---|
With water at 38℃; Rate constant; |
cis-5-norbornene-endo-2,3-dicarboxylic acid
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
Conditions | Yield |
---|---|
With 4-methyl-morpholine; methyl chloroformate In tetrahydrofuran at 20℃; for 0.25h; |
maleic anhydride
cyclopenta-1,3-diene
A
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
B
(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
Conditions | Yield |
---|---|
indium(III) chloride In water for 4h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With m-NO2C6H4BF2 In tetrahydrofuran at 0℃; for 1h; Title compound not separated from byproducts; | |
With m-NO2C6H4BF2 In tetrahydrofuran at 0℃; for 1h; Product distribution; other boron catalysts, other temperature regime; | |
Stage #1: maleic anhydride With (S)-BINOL-Silica Hybrid (BSH) In dichloromethane at 20℃; for 0.166667h; Diels-Alder Cycloaddition; Stage #2: cyclopenta-1,3-diene In dichloromethane at 20℃; for 2h; Diels-Alder Cycloaddition; Overall yield = 85 %; Optical yield = 84 %de; |
maleic anhydride
(1R,6S,7S)-5,5-Dimethyl-2,3-diaza-tricyclo[5.2.1.02,6]deca-3,8-diene
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
Conditions | Yield |
---|---|
With trifluoroacetic acid In chloroform-d1 for 336h; |
acetic acid
(+/-)-2exo-chloro-norborn-5-ene-2endo,3endo-dicarboxylic acid-anhydride
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
acetic acid
(1R,2S,3R,4S)-2,3-dibromobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
maleic anhydride
endo-Dicyclopentadien
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
Conditions | Yield |
---|---|
at 200℃; |
maleic anhydride
bi(cyclopentadiene)
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
Conditions | Yield |
---|---|
In tetrahydrofuran at 95 - 195℃; Solvent; Temperature; |
methanol
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
(1SR,2RS,3SR,4RS)-3-(methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
Conditions | Yield |
---|---|
for 16h; Reflux; | 100% |
With triethylamine at 20℃; for 12h; | 98% |
With triethylamine for 2h; Heating; | 97% |
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
Conditions | Yield |
---|---|
at 180℃; for 24h; | 100% |
With triethylamine In ethanol Mechanism; Irradiation; 2-6 h; other endo-Diels-Alder cycloadducts; | 94% |
With triethylamine In ethanol Irradiation; 2-6 h; | 94% |
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
(1R,2S,6R,7S)-4-azatricyclo[5.2.1.0(2,6)]dec-8-ene-3,5-dione
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid at 140℃; for 96h; Inert atmosphere; | 100% |
With ammonium acetate; acetic acid at 140℃; for 16h; | 100% |
With ammonium acetate at 135℃; Industrial scale; | 98.8% |
n-propylmagnesium bromide
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
dipropyl-5,5 oxa-4,10 endo-tricyclo<5.2.1.02.6>decene-8 one-3
Conditions | Yield |
---|---|
100% | |
In tetrahydrofuran; diethyl ether at 25℃; for 4h; | 90% |
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
(1R,2S,3R,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dimethanol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0℃; Reflux; | 100% |
With lithium aluminium tetrahydride In diethyl ether at 20℃; | 97% |
With lithium aluminium tetrahydride In tetrahydrofuran Heating; | 95% |
Conditions | Yield |
---|---|
With triethylamine at 65℃; for 24h; | 100% |
aniline
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
3-endo-(N-phenylcarbamoyl)bicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid
Conditions | Yield |
---|---|
In benzene at 20℃; | 99% |
1-amino-2-propene
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
(3aRS,4SR,7RS,7aSR)-2-allyl-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
In acetic acid for 16h; Inert atmosphere; Reflux; | 99% |
With acetic acid at 20 - 110℃; for 6h; Reflux; Inert atmosphere; | 89% |
With benzene |
benzylamine
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
(1α,2α,6α,7α)-4-benzyl-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
Conditions | Yield |
---|---|
In acetic acid for 5h; Inert atmosphere; Reflux; | 99% |
With triethylamine In toluene for 19h; Heating; | 93% |
In ethanol at 165 - 175℃; | 85% |
With benzene | |
With triethylamine In toluene for 5h; Reflux; |
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
cis-5-norbornene-endo-2,3-dicarboxylic anhydride
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In tetrahydrofuran under 75.006 Torr; | 99% |
With hydrogen; palladium 10% on activated carbon In tetrahydrofuran at 20℃; for 16h; Product distribution / selectivity; | 99% |
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 20℃; for 16h; | 99% |
methanol
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
(1R,2S,3R,4S)-3-(methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
Conditions | Yield |
---|---|
With (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(1-(dimethylamino)-3-methylbutan-2-yl)thiourea In tert-butyl methyl ether at 20℃; for 32h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
Stage #1: 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride With quinine In tetrachloromethane; toluene Inert atmosphere; Stage #2: methanol In tetrachloromethane; toluene at -55 - 25℃; Stage #3: With hydrogenchloride In water; ethyl acetate | 98% |
With textile immobilized (9S)-9-(3,5-di(trifluoromethyl)phenyl)sulfonamido-9-deoxyquinidine In tert-butyl methyl ether at 20℃; for 14h; enantioselective reaction; | 94% |
methanol
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
(1S,2R,3S,4R)-3-(methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
Conditions | Yield |
---|---|
With quinidine In tetrachloromethane; toluene | 99% |
With 1-((1R,2R)-2-(dimethylamino)cyclohexyl)-3-phenylthiourea In diethyl ether at 20℃; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
With quinidine In tetrachloromethane; toluene at -55℃; for 60h; Ring cleavage; methylation; | 98% |
Conditions | Yield |
---|---|
In benzene at 20℃; for 24h; | 99% |
N-BOC-1,2-diaminoethane
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
(1α,2α,6α,7α)-4-[2’-(tertbutoxycarbonylamino)ethyl]-4-azatricyclo[5.2.1.02,6]dec-8-en-3,5-dione
Conditions | Yield |
---|---|
In toluene at 100℃; for 0.5h; Microwave irradiation; | 99% |
In toluene at 100℃; for 0.5h; Microwave irradiation; | 99% |
In chloroform at 120℃; for 12h; | 80.9% |
ethylenediamine
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
[[3,5-dioxo-4-azatricyclo-[5.2.1.02,6]dec-8-en-4-yl]ethyl]-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
Conditions | Yield |
---|---|
In toluene for 120h; Reflux; Inert atmosphere; | 99% |
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 2h; Inert atmosphere; chemoselective reaction; | 99% |
Conditions | Yield |
---|---|
In acetic acid for 16h; Inert atmosphere; Reflux; | 99% |
Conditions | Yield |
---|---|
In toluene at 200℃; for 0.166667h; | 99% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 30℃; for 24h; | 98% |
Conditions | Yield |
---|---|
In benzene at 20℃; | 98% |
3-methylantranilic acid
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
C17H15NO4
Conditions | Yield |
---|---|
at 110℃; for 16h; Inert atmosphere; neat (no solvent); | 98% |
Conditions | Yield |
---|---|
With [(1,5-cyclooctadiene)(OH)iridium(I)]2 In 1,4-dioxane at 60℃; for 6h; Inert atmosphere; Schlenk technique; Sealed tube; diastereoselective reaction; | 98% |
Conditions | Yield |
---|---|
In toluene for 6h; Reflux; Dean-Stark; | 98% |
1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
Conditions | Yield |
---|---|
In N,N-dimethyl acetamide at 20℃; for 6h; Inert atmosphere; | 97.2% |
Conditions | Yield |
---|---|
With quinidine In tetrachloromethane; toluene at -55℃; for 60h; | 97% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 30℃; for 24h; | 97% |
N,N-dimethylethylenediamine
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
(1R,2S,6R,7S)-4-[2-(dimethylamino)ethyl]-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
Conditions | Yield |
---|---|
In toluene Reflux; | 97% |
In toluene at 80℃; | 86% |
In benzene at 110℃; for 18h; | 44% |
Conditions | Yield |
---|---|
In benzene at 20℃; | 97% |
S-methylisothiosemicarbazide hydroiodide
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
C11H13N3O2S
Conditions | Yield |
---|---|
Stage #1: S-methylisothiosemicarbazide hydroiodide; 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride With acetic acid for 1.5h; Reflux; Stage #2: With ammonia In water | 97% |
The Molecular Structure of Carbic anhydride (CAS NO.129-64-6):
Empirical Formula: C9H8O3
Molecular Weight: 164.158
Nominal Mass: 164 Da
Average Mass: 164.158 Da
Monoisotopic Mass: 164.047344 Da
Index of Refraction: 1.583
Molar Refractivity: 39.08 cm3
Molar Volume: 116.7 cm3
Surface Tension: 50.9 dyne/cm
Density: 1.405 g/cm3
Flash Point: 163.8 °C
Enthalpy of Vaporization: 57.37 kJ/mol
Boiling Point: 331.1 °C at 760 mmHg
Vapour Pressure: 0.00016 mmHg at 25°C
Melting Point: 164.5°C
log P (octanol-water): 1.850at 25°C
Atmospheric OH Rate Constant: 6.01E-11 cm3/molecule-secat 25°C
InChI
InChI=1/C9H8O3/c10-8-6-4-1-2-5(3-4)7(6)9(11)12-8/h1-2,4-7H,3H2/t4-,5-,6-,7+/m0/s1
Smiles
C1(OC(=O)[C@H]2[C@@H]1[C@H]1C=C[C@@H]2C1)=O
EINECS: 204-957-7
Carbic anhydride (CAS NO.129-64-6) is also called as 3,6-Endomethylene-delta4-tetrahydrophthalic anhydride ; Endic anhydride ; Nadic anhydride ; Endo-5-Norbornene-2,3-dicarboxylic anhydride ; Endo-Himic acid anhydride ; 4,7-Methanoisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydro-, (3aalpha,4alpha,7alpha,7aalpha)- (9CI) ; 5-Norbornene-2,3-dicarboxylic anhydride, cis-endo- (8CI) ; 8,9,10-Trinorborn-5-ene-2,3-dicarboxylic anhydride ; Endo-3,6-methylene-1,2,3,6-tetrahydrophthalic anhydride ; cis-5-Norbornene-endo-2,3-dicarboxylic anhydride .
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