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(1S,5R)-1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one
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Name

(1S,5R)-1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one

 EINECS 613-140-8
CAS No. 63106-93-4 Density 1.3 g/cm3
PSA 26.30000 LogP 1.50110
Solubility N/A Melting Point 49-50 °C
Formula C11H10O2 Boiling Point 340.05 °C at 760 mmHg
Molecular Weight 174.199 Flash Point 141.177 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 63106-93-4 ((1S,5R)-1-PHENYL-3-OXA-BICYCLO[3.1.0]HEXAN-2-ONE) Hazard Symbols N/A
Synonyms

3-Oxabicyclo[3.1.0]hexan-2-one,1-phenyl-;(1S,5R)-1-Phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one;

Article Data 35

(1S,5R)-1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one Synthetic route

145193-16-4

allyl α-phenyl-α-diazoacetate

63106-93-4

1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

Conditions
ConditionsYield
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%
140-29-4

phenylacetonitrile

106-89-8

epichlorohydrin

63106-93-4

1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

Conditions
ConditionsYield
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
106-89-8

epichlorohydrin

63106-93-4

1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

Conditions
ConditionsYield
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%
68-34-8

phenyl toluenesulfonamide

145193-16-4

allyl α-phenyl-α-diazoacetate

63106-93-4

1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

Conditions
ConditionsYield
With dirhodium tetraacetate In dichloromethane at 23℃;64%
168475-91-0

6a-Phenyl-3a,6a-dihydro-3H-furo[3,4-c]pyrazole-4,6-dione

A

33131-14-5

4-methyl-3-phenyl-2,5-dihydrofuran-2-one

B

1575-48-0

3-methyl-4-phenylfuran-2(5H)-one

C

63106-93-4

1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

D

96847-64-2, 121851-50-1

5-phenyl-3-oxabicyclo<3.1.0>hexan-2-one

Conditions
ConditionsYield
With sodium tetrahydroborate 1.) benzene, 70 deg C, 2.) THF, 0 deg C, 1 h; Yield given. Multistep reaction. Yields of byproduct given;
1797-74-6

allyl phenylacetate

63106-93-4

1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

Conditions
ConditionsYield
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
103-80-0

phenylacetyl chloride

Ala ester

Ala ester

63106-93-4

1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

Conditions
ConditionsYield
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

3-(2-bromophenyl)-3-methyldihydrofuran-2(3H)-one

A

63106-93-4

1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

B

C11H10O2

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium pivalate In dimethyl sulfoxide; toluene at 140℃; for 16h; Inert atmosphere;A 21 %Spectr.
B 48 %Spectr.

dimethyl 2-(2-bromophenyl)-2-methylsuccinate

A

63106-93-4

1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

B

C11H10O2

Conditions
ConditionsYield
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
115615-34-4

(±)-methyl 2-(2-bromophenyl)propanoate

A

63106-93-4

1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

B

C11H10O2

Conditions
ConditionsYield
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

(1S,5R)-1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one Chemical Properties

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

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