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Basic Information
| CAS No.: | 946-39-4 |
|---|---|
| Name: | ETHYL TRANS-2-PHENYLCYCLOPROPANECARBOXYLATE |
| Article Data: | 470 |
| Molecular Structure: | |
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|
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| Formula: | C12H14 O2 |
| Molecular Weight: | 190.242 |
| Synonyms: | Cyclopropanecarboxylicacid, 2-phenyl-, ethyl ester, trans- (8CI); (1R,2R)-rel-2-Phenylcyclopropanecarboxylicacid ethyl ester; Ethyl trans-2-phenyl-1-cyclopropanecarboxylate; Ethyltrans-2-phenylcyclopropane-1-carboxylate; Ethyltrans-2-phenylcyclopropanecarboxylate; NSC 74491; anti-Ethyl2-phenylcyclopropanecarboxylate; trans-2-Phenylcyclopropane-1-carboxylic acidethyl ester; trans-2-Phenylcyclopropanecarboxylic acid ethyl ester |
| Density: | 1.108g/cm3 |
| Melting Point: | 38 °C |
| Boiling Point: | 266.7°Cat760mmHg |
| Flash Point: | 106.9°C |
| PSA: | 26.30000 |
| LogP: | 2.35320 |
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Synthetic route
- 186581-53-3, 908094-01-9
diazomethane
- 4192-77-2
ethyl cinnamate
- 946-39-4
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
Conditions
| Conditions | Yield |
|---|---|
| With palladium diacetate In diethyl ether for 1h; Ambient temperature; | 98% |
- 292638-84-7
styrene
- 623-73-4
diazoacetic acid ethyl ester
- 946-39-4
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
Conditions
| Conditions | Yield |
|---|---|
| With [Ru(4-F-TPP)(BIMe)2] In dichloromethane at 20℃; for 0.333333h; Inert atmosphere; | 98% |
| With dirhodium tetraacetate In dichloromethane for 24h; Inert atmosphere; | 89% |
| With hemin; glycine ethyl ester hydrochloride; acetic acid; sodium nitrite In water at 40℃; for 24h; | 50% |
| With sodium dithionite; κ-NHis-(apo heme myoglobin H64V mutant)-κ-C-(2-ethoxy-2-oxoethylidene)ruthenium mesoporphyrin IX In aq. phosphate buffer at 20℃; for 18h; pH=7; Catalytic behavior; Reagent/catalyst; pH-value; Inert atmosphere; Sealed tube; Green chemistry; Enzymatic reaction; diastereoselective reaction; | 8.4 %Chromat. |
- 64-17-5
ethanol
- 939-90-2
trans-2-phenylcyclopropane-1-carboxylic acid
- 946-39-4
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
Conditions
| Conditions | Yield |
|---|---|
| With hydrogenchloride for 8h; Heating; | 92% |
| With toluene-4-sulfonic acid Reflux; | 91% |
- 96-09-3
styrene oxide
- 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester
- 946-39-4
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With n-butyllithium In 1,4-dioxane at 0℃; for 0.5h; Stage #2: styrene oxide at 135℃; for 1h; Microwave irradiation; | 91% |
| With n-butyllithium In 1,2-dimethoxyethane at 135℃; for 1h; Microwave irradiation; |
- 64-17-5
ethanol
- 939-89-9, 939-90-2, 3471-10-1, 5685-38-1, 23020-15-7, 23020-18-0, 42916-14-3, 48126-51-8, 67528-68-1, 111956-00-4, 111956-01-5
(1S*,2R*)-2-phenylcyclopropane-1-carboxylic acid
- 946-39-4
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
Conditions
| Conditions | Yield |
|---|---|
| With hydrogenchloride for 8h; Heating; | 89% |
- 186581-53-3, 908094-01-9
diazomethane
- 623-73-4
diazoacetic acid ethyl ester
- 100-52-7
benzaldehyde
- 946-39-4
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: diazoacetic acid ethyl ester; benzaldehyde With copper(l) iodide; triphenylphosphine In dichloromethane at 40℃; Inert atmosphere; Stage #2: diazomethane With tris(dibenzylideneacetone)dipalladium (0) In dichloromethane at -78℃; Inert atmosphere; diastereoselective reaction; | 85% |
...Expand
Conditions
| Conditions | Yield |
|---|---|
| With palladium diacetate; caesium carbonate; catacxium A In water; toluene at 110℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; Reflux; diastereoselective reaction; | 84% |
- 1774-47-6
trimethylsulfoxonium iodide
- 4192-77-2
ethyl cinnamate
- 946-39-4
ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate
Conditions
| Conditions | Yield |
|---|---|
| With sodium hydride In tetrahydrofuran; dimethyl sulfoxide at 25℃; Inert atmosphere; | 79% |
| Stage #1: trimethylsulfoxonium iodide With sodium hydride In dimethyl sulfoxide for 1h; Inert atmosphere; Stage #2: ethyl cinnamate In dimethyl sulfoxide at 0 - 65℃; for 108h; Inert atmosphere; | |
| Stage #1: trimethylsulfoxonium iodide With sodium hydride In dimethyl sulfoxide for 1h; Inert atmosphere; Stage #2: ethyl cinnamate In dimethyl sulfoxide at 0 - 65℃; for 108h; Inert atmosphere; |
Conditions
| Conditions | Yield |
|---|---|
| With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In dimethyl sulfoxide at 35℃; for 3h; Inert atmosphere; Sealed tube; Irradiation; chemoselective reaction; | 75% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: (E)-ethyl 2-(benzenesulfinyl)cyclopropane-1-carboxylate With isopropylmagnesium chloride In tetrahydrofuran at -78℃; for 0.166667h; Inert atmosphere; Stage #2: With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; zinc(II) chloride In tetrahydrofuran at 0℃; for 1h; Negishi Coupling; Inert atmosphere; Stage #3: bromobenzene In tetrahydrofuran at 25℃; for 15h; Negishi Coupling; Inert atmosphere; | 74% |
