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

Name
(1S,5R)-1-PHENYL-3-OXA-BICYCLO[3.1.0]HEXAN-2-ONE
EINECS 613-140-8
CAS No. 63106-93-4
Article Data35
CAS DataBase
Density 1.3 g/cm³
Solubility
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
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 3-Oxabicyclo[3.1.0]hexan-2-one,1-phenyl-;(1S,5R)-1-Phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one;
PSA 26.30000
LogP 1.50110

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

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%

: 140-29-4
phenylacetonitrile

: 106-89-8
epichlorohydrin

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

Conditions

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

: 106-89-8
epichlorohydrin

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

Conditions

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%

: 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

Conditions	Yield
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

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;

...Expand

: 1797-74-6
allyl phenylacetate

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

Conditions

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

: 103-80-0
phenylacetyl chloride

Ala ester: Ala ester

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

Conditions

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

: 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

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.

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

A: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

B: C11H10O2

Conditions

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

: 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

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

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

: 2-(bromomethyl)-1-phenylcyclopropanecarboxylic acid

Conditions

Conditions	Yield
With hydrogen bromide at 80℃; for 2h;	98%

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

: 69160-63-0
(1S,2R)/(1R,2S)-2-(bromomethyl)-1-phenylcyclopropanecarboxylic acid

Conditions

Conditions	Yield
With hydrogen bromide In acetic acid at 80℃; for 2h;	96%
With hydrogen bromide In acetic acid at 80℃; for 2h;

: 67-56-1
methanol

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

: C12H13ClO2

Conditions

Conditions	Yield
With thionyl chloride at 20℃; for 10h; Temperature;	94.5%

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

: 109-89-7
diethylamine

: 1-phenyl-1-diethylaminocarbonyl-2-hydroxymethylcyclopropane

Conditions

Conditions	Yield
Stage #1: 1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one; diethylamine With sodium methylate In methanol; toluene at 20 - 30℃; for 8h; Stage #2: With water; acetic acid In methanol; toluene	93.8%

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

: 64-17-5
ethanol

: 105310-49-4
ethyl (+/-)-cis-2-(bromomethyl)-1-phenylcyclopropanecarboxylate

Conditions

Conditions	Yield
With dibromo sulfoxide at -15 - 20℃;	90%

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

: 109-89-7
diethylamine

: (Z)-1-phenyl-1-diethylaminocarbonyl-2-hydroxymethylcyclopropane

Conditions

Conditions	Yield
With sodium methylate In methanol; toluene at 20 - 30℃; for 15h; Product distribution / selectivity;	87%
With sodium methylate In toluene at 60℃; for 15h; Product distribution / selectivity;
With sodium methylate In methanol at 20 - 60℃; for 15h; Product distribution / selectivity;

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

: 172016-06-7
(1R,2S)-1-phenyl-2-(hydroxymethyl)-N,N-diethylcyclopropanecarboxamide

Conditions

Conditions	Yield
Stage #1: diethylamine With n-butyllithium In tetrahydrofuran; hexane at -75℃; for 1h; Stage #2: 1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one In tetrahydrofuran; hexane at -78 - -60℃; Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane	66.8%

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

: 1074-82-4
potassium phtalimide

: 69160-56-1
(Z)-1-phenyl-2-(phthalimidomethyl)cyclopropanecarboxylic acid

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 15h; Heating;	57%

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

: 1074-82-4
potassium phtalimide

: 2-((1,3-dioxoisoindolin-2-yI)methyI)-1-phenylcyclopropane carboxylic acid

Conditions

Conditions	Yield
Stage #1: 1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one; potassium phtalimide In dimethyl sulfoxide at 150℃; for 20h; Stage #2: With acetic acid pH=5 - 6; Product distribution / selectivity;	51%
Stage #1: 1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one; potassium phtalimide With tetra-(n-butyl)ammonium iodide In 1-methyl-pyrrolidin-2-one at 150℃; for 20h; Stage #2: With acetic acid pH=5 - 6; Product distribution / selectivity;	> 90 %Chromat.
Stage #1: 1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one; potassium phtalimide In 1-methyl-pyrrolidin-2-one at 150℃; for 20h; Stage #2: With acetic acid pH=5 - 6; Product distribution / selectivity;	> 90 %Chromat.
Stage #1: 1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one; potassium phtalimide In DMF (N,N-dimethyl-formamide) at 50 - 150℃; for 20 - 24h; Stage #2: With acetic acid pH=5 - 6; Product distribution / selectivity;	70 - > 90 %Chromat.

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

: phenylmagnesium bromide

: 139048-20-7
1,2-diphenyl-2-hydroxy-3-oxabicyclo <3,1,0> hexane

Conditions

Conditions	Yield
In diethyl ether for 1.5h; Heating;	47%

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

: 3886-69-9
(R)-1-phenyl-ethyl-amine

: (+)-2-Hydroxymethyl-1-phenylcyclopropanecarboxylic acid (1-phenylethyl)amide

: (-)-2-Hydroxymethyl-1-phenylcyclopropanecarboxylic acid (1-phenylethyl)amide

Conditions

Conditions	Yield
With 2-hydroxypyridin In toluene for 24h; Heating;	A 33% B 32%

...Expand

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

A: 2-(hydroxymethyl)-1-phenylcyclopropane-1-carboxylic acid

B: 63106-93-4, 96847-52-8, 96847-75-5, 96847-53-9
(1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one

Conditions

Conditions	Yield
With Cunninghamella blakesleeana; water In N,N-dimethyl-formamide at 30℃; for 41h; biohydrolysis, pH 8;	A n/a B 32%

: 288-13-1
NH-pyrazole

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

: 141402-58-6
(1R,2S)-1-Phenyl-2-pyrazol-1-ylmethyl-cyclopropanecarboxylic acid

Conditions

Conditions	Yield
With sodium hydride 1.) DMF, 60 deg C, 1 h, 2.) DMF, 60 deg C, 5 h; Yield given. Multistep reaction;

: 636-41-9
2-methyl-1H-pyrrole

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

: 141402-55-3
(1S,2R)-2-(2-Methyl-pyrrol-1-ylmethyl)-1-phenyl-cyclopropanecarboxylic acid

Conditions

Conditions	Yield
With sodium hydride 1.) DMF, 60 deg C, 1 h, 2.) DMF, 60 deg C, 5 h; Yield given. Multistep reaction;

: 120-72-9
indole

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

: 141402-56-4
(1R,2S)-2-Indol-1-ylmethyl-1-phenyl-cyclopropanecarboxylic acid

Conditions

Conditions	Yield
With sodium hydride 1.) DMF, 60 deg C, 1 h, 2.) DMF, 60 deg C, 5 h; Yield given. Multistep reaction;

: 67-56-1
methanol

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

: 105310-48-3
(+/-)-methyl cis-2-(bromomethyl)-1-phenylcyclopropanecarboxylate

Conditions

Conditions	Yield
With dibromo sulfoxide at -15 - 20℃;

: 71-23-8
propan-1-ol

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

: 105310-50-7
n-propyl (1R,2S/1S,2R)-2-(chloromethyl)-1-phenylcyclopropanecarboxylate

Conditions

Conditions	Yield
With thionyl chloride at -15 - 20℃;

: 83-34-1
3-Methylindole

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

: 141402-57-5
(1S,2R)-2-(3-Methyl-indol-1-ylmethyl)-1-phenyl-cyclopropanecarboxylic acid

Conditions

Conditions	Yield
With sodium hydride 1.) DMF, 60 deg C, 1 h, 2.) DMF, 60 deg C, 5 h; Yield given. Multistep reaction;

: 109-97-7
pyrrole

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

: 141402-53-1
(1R,2S)-1-Phenyl-2-pyrrol-1-ylmethyl-cyclopropanecarboxylic acid

Conditions

Conditions	Yield
With sodium hydride 1.) DMF, 60 deg C, 1 h, 2.) DMF, 60 deg C, 5 h; Yield given. Multistep reaction;

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

: 67-63-0
isopropyl alcohol

: 105310-51-8
(Z)-isopropyl 1-phenyl-2-(phthalimidomethyl)cyclopropanecarboxylate

Conditions

Conditions	Yield
With thionyl chloride at -15 - 20℃;

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

: 109-89-7
diethylamine

: 172015-99-5
(1 S,2 R)-N,N-diethyl-2-(hydroxymethyl)-1-phenylcyclopropane-carboxamide

Conditions

Conditions	Yield
With n-butyllithium 1) THF, hexane, 0 - -78 deg C; 2) THF, hexane, -78 deg C, 2 h; Yield given. Multistep reaction;

: 67-56-1
methanol

: 63106-93-4
1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

: (1R,2S)-2-Chloromethyl-1-phenyl-cyclopropanecarbonyl chloride

Conditions

Conditions	Yield
With thionyl chloride; zinc(II) chloride In benzene

(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

Product Name

(1S,5R)-1-PHENYL-3-OXA-BICYCLO[3.1.0]HEXAN-2-ONE

Synthetic route

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

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