ethyl (1R,2S)-2-phenylcyclopropanecarboxylate

Base Information

• Chemical Name: ethyl (1R,2S)-2-phenylcyclopropanecarboxylate
• CAS No.: 946-38-3
• Molecular Formula: C12H14O2
• Molecular Weight: 190.242
• Mol file: 946-38-3.mol

Synonyms:

Chemical Property of ethyl (1R,2S)-2-phenylcyclopropanecarboxylate

Chemical Property:

• Vapor Pressure: 0.00851mmHg at 25°C

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (1R,2S)-2-phenylcyclopropanecarboxylate

There total 222 articles about ethyl (1R,2S)-2-phenylcyclopropanecarboxylate 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: 87.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + diazoacetic acid ethyl ester (623-73-4) → ethyl 2-phenylcyclopropylcarboxylate (946-38-3,946-39-4,34702-96-0,34702-97-1,34703-00-9,34716-60-4,63038-62-0,63038-63-1,97-71-2) + diethyl Fumarate (623-91-6) + Diethyl maleate (141-05-9)

Guidance literature:

hexarhodium hexadecacarbonyl; at 25 ℃; for 7h;

DOI:10.1016/S0040-4039(01)90438-1

Reference yield: 72.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + diazoacetic acid ethyl ester (623-73-4) → ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate (946-39-4) + cis-1-ethoxycarbonyl-2-phenylcyclopropane (946-38-3) + diethyl Fumarate (623-91-6)

Guidance literature:

With dirhodium tetraacetate; In dichloromethane; at 20 ℃; for 1.58333h; Reagent/catalyst;

DOI:10.1002/ejoc.201800953

Reference yield: 53.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + diazoacetic acid ethyl ester (623-73-4) → ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate (946-39-4) + cis-1-ethoxycarbonyl-2-phenylcyclopropane (946-38-3) + Diethyl maleate (141-05-9)

Guidance literature:

With [Fe(tpfc)Cl]; at 22 - 25 ℃; Further Variations:; Reagents; Product distribution;

DOI:10.1002/1521-3765(20010302)7:5<1041::AID-CHEM1041>3.0.CO;2-8

upstream raw materials:

styrene

diazoacetic acid ethyl ester

(1R,2S)-ethyl 2-phenylcyclopropane-1-carboxylate

ethanol

Downstream raw materials:

ethyl (S,S)-2-phenylcyclopropane-1-carboxylate

(1R,2S)-2-phenylcyclopropane-1-carboxylic acid

(1R,2R)-trans-2-phenyl-1-cyclopropanecarboxylic acid

trans-diphenyl(2-phenylcyclopropyl)methanol

Refernces

• 1、 Wolf, Jennifer Robbins,Hamaker, Christopher G.,Djukic, Jean-Pierre,Kodadek, Thomas,Woo, L. Keith. "Shape and stereoselective cyclopropanation of alkenes catalyzed by iron porphyrins". . p. 9194 - 9199. Retrieved 1995.
• 2、 Eagle, Cassandra T.,Farrar, David,Holder, Grant N.,Hatley, Michelle L.,Humphrey, Shirley L.,Olson, Elizabeth V.,Quintos, Maria,Sadighi, Joseph,Wideman, Tom. "cis-Enhanced cyclopropanation catalysts: Reaction chemistry of three isomers of Rh2[N(C6H5)COCH3]4". . p. 2593 - 2595. Retrieved 2003.
• 3、 Rosenberg, Marianne L.,Krapp, Andreas,Tilset, Mats. "On the mechanism of cyclopropanation reactions catalyzed by a rhodium(I) catalyst bearing a chelating imine-functionalized NHC ligand: A computational study". . p. 6562 - 6571. Retrieved 2011.
• 4、 Callot, H. J.,Piechocki, C.. "CYCLOPROPANATION USING RHODIUM(III)PORPHYRINS : LARGE CIS VS TRANS SELECTIVITY". . p. 3489 - 3492. Retrieved 1980.
• 5、 Cheng, Shun-Cheung,Cheung, Wai-Man,Chong, Man-Chun,Ko, Chi-Chiu,Leung, Wa-Hung,Sung, Herman H.-Y.,Williams, Ian D.. "Synthesis, structure and reactivity of iridium complexes containing a bis-cyclometalated tridentate C^N^C ligand". . p. 8512 - 8523. Retrieved 2021/06/28.
• 6、 Ababneh, Taher S.,Al-Dawood, Lina A.,Al-Momani, Waleed M.,Hijazi, Ahmed K.,Taha, Ziyad A.. "Catalytic cyclopropanation, antimicrobial, and DFT properties of some chelated transition metal(II) complexes". . . Retrieved 2020/12/25.