Oxiranecarboxylic acid, 3-phenyl-, ethyl ester, trans-

Base Information

• Chemical Name: Oxiranecarboxylic acid, 3-phenyl-, ethyl ester, trans-
• CAS No.: 2272-55-1
• Molecular Formula: C11H12 O3
• Molecular Weight: 192.214
• Hs Code.: 2918990090
• Mol file: 2272-55-1.mol

Synonyms:Glycidicacid, 3-phenyl-, ethyl ester, trans- (8CI); Oxiranecarboxylic acid, 3-phenyl-,ethyl ester, (2R,3S)-rel- (9CI); Oxiranecarboxylic acid, 3-phenyl-, ethylester, trans-; (?à)-trans-3-Phenyloxirane-2-carboxylicacid ethyl ester; Ethyl trans-3-phenylglycidate; NSC 82271; trans-Et cinnamateepoxide; trans-Ethyl 3-phenylglycidate

Chemical Property of Oxiranecarboxylic acid, 3-phenyl-, ethyl ester, trans-

Chemical Property:

• Melting Point: 63-64℃
• Boiling Point: 292.4°Cat760mmHg
• Flash Point: 107.7°C
• PSA: 38.83000
• Density: 1.182g/cm³
• LogP: 1.68960

Purity/Quality:

99% ^*data from raw suppliers

(2R,3S)-ETHYL 3-PHENYLOXIRANE-2-CARBOXYLATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Oxiranecarboxylic acid, 3-phenyl-, ethyl ester, trans-

There total 84 articles about Oxiranecarboxylic acid, 3-phenyl-, ethyl ester, trans- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

(2R,3R) ethyl 2-chloro-3-hydroxy-3-phenylpropionate (146452-40-6) → (2S,3R)-ethyl 3-phenyloxirane-2-carboxylate (121-39-1,2272-49-3,2272-55-1,54276-44-7,56791-22-1,126060-73-9,130321-77-6,130321-78-7,130605-53-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/0040-4039(95)00182-C

Reference yield: 87.0%

(E)-ethyl 4-styrylbenzoate (1152-30-3,109463-49-2,109463-48-1) → (2S,3R)-ethyl 3-phenyloxirane-2-carboxylate (121-39-1,2272-49-3,2272-55-1,54276-44-7,56791-22-1,126060-73-9,130321-77-6,130321-78-7,130605-53-7)

Guidance literature:

With (5S,8R,9R)-2,2-dimethyl-10-oxo-1,3,6-trioxaspiro[4.5]decane-8,9-diyl diacetate; Na₂EDTA; oxone; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; In water; acetonitrile; at 28 ℃; for 24h; pH=7 - 8; optical yield given as %ee;

DOI:10.1002/adsc.201100735

Reference yield: 73.0%

ethyl cinnamate (4192-77-2) → (2S,3R)-ethyl 3-phenyloxirane-2-carboxylate (121-39-1,2272-49-3,2272-55-1,54276-44-7,56791-22-1,126060-73-9,130321-77-6,130321-78-7,130605-53-7)

Guidance literature:

With Oxone; edetate disodium; sodium hydrogencarbonate; (5S,8R,9R)-c(C(O)C(c(OC(CH₃)2OCH₂))OCH₂CHOAcCHOAc); tetra(n-butyl)ammonium hydrogensulfate; In acetonitrile; at 0 - 20 ℃; for 24h;

DOI:10.1021/ja020478y

upstream raw materials:

ethanol

erythro-2,3-dibromo-3-phenylpropanoic acid

sodium acetate

benzaldehyde

Downstream raw materials:

(2-nitro-phenylsulfanyl)-acetic acid ethyl ester

2-Hydroxy-3-(2-nitro-phenylsulfanyl)-3-phenyl-propionic acid ethyl ester

(2S,3S)-2-Hydroxy-3-phenyl-heptanoic acid ethyl ester

ethyl 2-hydroxy-3-phenyl-5-(trimethylsilyl)-4-pentynoate

Refernces

• 1、 Xu, Ya-Nan,Tian, Shi-Kai. "Facile construction of three-membered rings via benzyne-promoted Darzens-type reaction of tertiary amines". . p. 1632 - 1638. Retrieved 2018/12/13.
• 2、 Zhao, Wei,Kotik, Michael,Iacazio, Gilles,Archelas, Alain. "Enantioselective bio-hydrolysis of various racemic and meso aromatic epoxides using the recombinant epoxide hydrolase Kau2". . p. 1895 - 1908. Retrieved 2015/06/02.