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CAS No.: | 182699-77-0 |
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Name: | 3A,4,5,7A-TETRAHYDRO-3,6-DIMETHYLBENZOFURAN-2(3H)-ONE |
Article Data: | 8 |
Molecular Structure: | |
Formula: | C10H14 O2 |
Molecular Weight: | 166.22 |
Synonyms: | 2(3H)-Benzofuranone,3a,4,5,7a-tetrahydro-3,6-dimethyl-, [3S-(3a,3aa,7aa)]-; (-)-(3S,3aS,7aR)-Winelactone; (-)-Wine lactone; Wine lactone |
Density: | 1.042 g/cm3 |
Boiling Point: | 286.3 ºC at 760 mmHg |
Flash Point: | 115.5 ºC |
PSA: | 26.30000 |
LogP: | 1.90420 |
(3aS,7aS)-6-methyl-3-methylene-3a,4,5,7a-tetrahydrobenzofuran-2(3H)-one
A
(-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one
B
(+)-(3aR,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one
Conditions | Yield |
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With [NH2Me2][{RuCl((S)-segphos)}2(μ-Cl)3]; hydrogen In 1,4-dioxane at 40℃; under 15001.5 Torr; for 6h; Inert atmosphere; Autoclave; diastereoselective reaction; | A n/a B 99% |
With [NH2Me2][{RuCl((R)-H8-binap)}2(μ-Cl)3]; hydrogen In 1,4-dioxane at 30℃; under 15001.5 Torr; for 16h; Inert atmosphere; Autoclave; diastereoselective reaction; | A 69% B n/a |
With sodium tetrahydroborate In ethanol at 20℃; for 1.5h; Product distribution; Further Variations:; Reagents; | A 5 % Chromat. B 92 % Chromat. |
With magnesium In methanol at 20℃; for 3h; |
(+)-(3aS,7aR)-2,3,3a,4,5,7a-hexahydro-6-methylbenzofuran-2(3H)-one
methyl iodide
(-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one
Conditions | Yield |
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Stage #1: (+)-(3aS,7aR)-2,3,3a,4,5,7a-hexahydro-6-methylbenzofuran-2(3H)-one With n-butyllithium; diisopropylamine In tetrahydrofuran at -20 - 0℃; for 1h; Inert atmosphere; Stage #2: methyl iodide With 1,3-dimethyl-2-imidazolidinone In tetrahydrofuran at 0 - 20℃; for 5h; Inert atmosphere; | 90% |
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1.5h; Alkylation; | 79% |
(3S,3aS,6R,7R,7aR)-(3a,4,5,6,7,7a)-hexahydro-3,6-dimethylbenzofuran-2(3H)-one
(-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one
Conditions | Yield |
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With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 5h; | 76% |
(2RS)-2-<(1R)-4-methylcyclohex-3-enyl>propanoic acid
A
(-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one
B
(+)-(3aR,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one
Conditions | Yield |
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With tert.-butylhydroperoxide; dipyridinium dichromate; Celite In N,N-dimethyl-formamide at 30℃; for 12h; | |
With tert.-butylhydroperoxide; dipyridinium dichromate; Celite In benzene at 30℃; for 12h; |
(3S,3aS,7aS)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one
(-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one
Conditions | Yield |
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With hydrogenchloride; sodium hydroxide 1.) water/MeOH, 80 deg C, 2 h, 2.) water/MeOH, 80 deg C, 2 h; Yield given. Multistep reaction; |
(3R,3aS,7aS)-3,6-dimethyl-3,3a,4,5-tetrahydrobenzofuran-2(7aH)-one
(-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one
Conditions | Yield |
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With hydrogenchloride; sodium hydroxide 1.) water/MeOH, 80 deg C, 2 h, 2.) water/MeOH, 80 deg C, 2 h; Yield given. Multistep reaction; |
2-((1R,4R)-4-Methyl-cyclohex-2-enyl)-propionic acid
(-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one
Conditions | Yield |
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Multi-step reaction with 2 steps 1: FeCl3; NaI / acetonitrile / 2.5 h / Heating 2: 76 percent / DBU / tetrahydrofuran / 5 h / 20 °C View Scheme |
(-)-(3aS,7R,7aR)-hexahydro-7-iodo-benzo[b]furan-2-one
(-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one
Conditions | Yield |
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Multi-step reaction with 5 steps 1: 82 percent / DBU / tetrahydrofuran / 3 h / Heating 2: 87 percent / CuBr*Me2S / tetrahydrofuran / 12 h / -10 °C 3: 60 percent / KI; I2; NaHCO3 / tetrahydrofuran; H2O / 2 h / 20 °C 4: 92 percent / DBU / tetrahydrofuran / 2 h / Heating 5: 79 percent / LDA / tetrahydrofuran / 1.5 h / -78 °C View Scheme |
methyl (+)-(S)-(cyclohex-2-enyl)acetate
(-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one
Conditions | Yield |
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Multi-step reaction with 7 steps 1: 95 percent / NaOH / 1 h / 120 °C 2: 66 percent / KI; I2; NaHCO3 / H2O / 5 h / 20 °C 3: 82 percent / DBU / tetrahydrofuran / 3 h / Heating 4: 87 percent / CuBr*Me2S / tetrahydrofuran / 12 h / -10 °C 5: 60 percent / KI; I2; NaHCO3 / tetrahydrofuran; H2O / 2 h / 20 °C 6: 92 percent / DBU / tetrahydrofuran / 2 h / Heating 7: 79 percent / LDA / tetrahydrofuran / 1.5 h / -78 °C View Scheme |
dimethyl 2-(cyclohex-2-en-1-yl)propanedioate
(-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one
Conditions | Yield |
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Multi-step reaction with 8 steps 1: 74 percent / NaCl / H2O; dimethylsulfoxide / 24 h / 160 °C 2: 95 percent / NaOH / 1 h / 120 °C 3: 66 percent / KI; I2; NaHCO3 / H2O / 5 h / 20 °C 4: 82 percent / DBU / tetrahydrofuran / 3 h / Heating 5: 87 percent / CuBr*Me2S / tetrahydrofuran / 12 h / -10 °C 6: 60 percent / KI; I2; NaHCO3 / tetrahydrofuran; H2O / 2 h / 20 °C 7: 92 percent / DBU / tetrahydrofuran / 2 h / Heating 8: 79 percent / LDA / tetrahydrofuran / 1.5 h / -78 °C View Scheme |