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allyl α-phenyl-α-diazoacetate
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one
Conditions | Yield |
---|---|
With dirhodium(II) tetrakis[methyl2-oxaazetidine-4(S)carboxylate] In dichloromethane for 0.5h; Cyclization; Heating; | 80% |
With dirhodium tetraacetate; trimethylsilylazide In dichloromethane at 40℃; for 1h; Reagent/catalyst; | 78% |
Conditions | Yield |
---|---|
Stage #1: phenylacetonitrile; epichlorohydrin With sodium hydride In N,N'-dimethylimidazolidinone; toluene at 10 - 20℃; Stage #2: With potassium hydroxide; tetrabutylammonium sulfate In water; toluene Heating / reflux; Stage #3: With hydrogenchloride In water; toluene at 60 - 70℃; for 2h; | 68.1% |
Stage #1: phenylacetonitrile With sodium hydride In 1,3-dimethyl-2-imidazolidinone; toluene at 10 - 20℃; for 2h; Stage #2: epichlorohydrin In 1,3-dimethyl-2-imidazolidinone; toluene at 10 - 20℃; Stage #3: With hydrogenchloride; potassium hydroxide; tetrabutylammonium sulfate more than 3 stages; | 68.1% |
Stage #1: phenylacetonitrile With sodium amide In benzene at 35℃; for 3h; Cooling with ice; Stage #2: epichlorohydrin In benzene at 35℃; for 4h; Cooling with ice; Stage #3: With potassium hydroxide In ethanol; water for 16.5h; Reflux; | |
Stage #1: phenylacetonitrile at 0 - 20℃; for 3h; Stage #2: epichlorohydrin at 0 - 20℃; for 4h; Stage #3: With potassium hydroxide In ethanol; water Reflux; | 14.5 g |
epichlorohydrin
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one
Conditions | Yield |
---|---|
Stage #1: phenylacetonitrile With sodium hydride In 1,3-dimethyl-2-imidazolidinone; toluene at 10 - 20℃; for 2h; Stage #2: epichlorohydrin In 1,3-dimethyl-2-imidazolidinone; toluene at 10 - 20℃; Stage #3: With hydrogenchloride; potassium hydroxide; tetrabutylammonium sulfate more than 3 stages; | 68.1% |
phenyl toluenesulfonamide
allyl α-phenyl-α-diazoacetate
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one
Conditions | Yield |
---|---|
With dirhodium tetraacetate In dichloromethane at 23℃; | 64% |
6a-Phenyl-3a,6a-dihydro-3H-furo[3,4-c]pyrazole-4,6-dione
A
4-methyl-3-phenyl-2,5-dihydrofuran-2-one
B
3-methyl-4-phenylfuran-2(5H)-one
C
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one
D
5-phenyl-3-oxabicyclo<3.1.0>hexan-2-one
Conditions | Yield |
---|---|
With sodium tetrahydroborate 1.) benzene, 70 deg C, 2.) THF, 0 deg C, 1 h; Yield given. Multistep reaction. Yields of byproduct given; |
allyl phenylacetate
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 74 percent / 1,8-diazobicyclo[5.4.0]undec-7-ene; p-acetamidobenzenesulfonyl azide / tetrahydrofuran / 11 h / 20 °C 2: 80 percent / dirhodium(II) tetrakis[methyl2-oxaazetidine-4(S)carboxylate] / CH2Cl2 / 0.5 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1.1: 4-acetamidobenzenesulfonyl azide / acetonitrile / 0.25 h / Inert atmosphere; Cooling with ice 1.2: 16 h / 20 °C / Inert atmosphere 2.1: dirhodium tetraacetate; trimethylsilylazide / dichloromethane / 1 h / 40 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Et3N 2: 74 percent / 1,8-diazobicyclo[5.4.0]undec-7-ene; p-acetamidobenzenesulfonyl azide / tetrahydrofuran / 11 h / 20 °C 3: 80 percent / dirhodium(II) tetrakis[methyl2-oxaazetidine-4(S)carboxylate] / CH2Cl2 / 0.5 h / Heating View Scheme |
A
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium pivalate In dimethyl sulfoxide; toluene at 140℃; for 16h; Inert atmosphere; | A 21 %Spectr. B 48 %Spectr. |
A
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diisobutylaluminium hydride / tetrahydrofuran / 16 h / 0 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium pivalate / toluene; dimethyl sulfoxide / 16 h / 140 °C / Inert atmosphere View Scheme |
(±)-methyl 2-(2-bromophenyl)propanoate
A
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C 1.2: 16 h / -78 - 20 °C 2.1: diisobutylaluminium hydride / tetrahydrofuran / 16 h / 0 °C 3.1: tetrakis(triphenylphosphine) palladium(0); potassium pivalate / toluene; dimethyl sulfoxide / 16 h / 140 °C / Inert atmosphere View Scheme |
Product Name: 1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one
Synonyms of 1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one (CAS NO.63106-93-4): (1S,5R)-1-Phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one
CAS NO: 63106-93-4
Molecular Formula of 1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one (CAS NO.63106-93-4): C11H10O2
Molecular Weight: 174.1959
Molecular Structure:
H bond acceptors: 2
Freely Rotating Bonds: 1
Polar Surface Area: 26.3 Å2
Index of Refraction: 1.622
Molar Refractivity: 47.192 cm3
Molar Volume: 133.958 cm3
Surface Tension: 54.955 dyne/cm
Density: 1.3 g/cm3
Flash Point: 141.177 °C
Enthalpy of Vaporization: 58.356 kJ/mol
Boiling Point of 1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one (CAS NO.63106-93-4): 340.05 °C at 760 mmHg