(1S,2R)-2-Phenylcyclopropanecarboxylic acid

Base Information

• Chemical Name: (1S,2R)-2-Phenylcyclopropanecarboxylic acid
• CAS No.: 939-89-9
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.188
• UNII: 7V3W75X6M2,R5Y6RJ2VZ6
• Nikkaji Number: J88.135J
• Mol file: 939-89-9.mol

Synonyms:(1S,2R)-2-Phenylcyclopropanecarboxylic acid;23020-18-0;(1S,2R)-2-phenylcyclopropane-1-carboxylic acid;R5Y6RJ2VZ6;Cyclopropanecarboxylic acid, 2-phenyl-, (1S,2R)-;2-Phenyl-1-cyclopropanecarboxylic acid, cis-(+)-;2-Phenyl-1-cyclopropanecarboxylic acid, (1S-cis)-;Cyclopropanecarboxylic acid, 2-phenyl-, (1S-cis)-;Cyclopropanecarboxylic acid, 2-phenyl-, (1S,2R)-(+)-;7V3W75X6M2;CIS-2-PHENYLCYCLOPROPANECARBOXYLIC ACID;2-Phenyl-1-cyclopropanecarboxylic acid, cis-(+/-)-;UNII-R5Y6RJ2VZ6;rel-((1S,2R)-2-Phenylcyclopropane-1-carboxylic acid);SCHEMBL8295172;AMY23733;MFCD20488809;AS-48639;(1S,2R)-2-Phenylcyclopropanecarboxylicacid;CS-0053583;(+/-)-cis-2-phenylcyclopropanecarboxylic acid;EN300-207385;F52068;(1s,2r)-rel-2-Phenylcyclopropanecarboxylic acid;CIS-2-PHENYL-1-CYCLOPROPANECARBOXYLIC ACID;CYCLOPROPANECARBOXYLIC ACID, 2-PHENYL-, CIS-;rel-((1S,2R)-2-phenylcyclopropane-1-carboxylicacid);Z1262510970;CYCLOPROPANECARBOXYLIC ACID, 2-PHENYL-, (1R,2S)-REL-

Chemical Property of (1S,2R)-2-Phenylcyclopropanecarboxylic acid

Chemical Property:

• Vapor Pressure: 0.000165mmHg at 25°C
• Melting Point: 105 °C
• Boiling Point: 317.1°Cat760mmHg
• PKA: 4.57±0.10(Predicted)
• Flash Point: 144.3°C
• PSA: 37.30000
• Density: 1.25g/cm³
• LogP: 1.87470
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 162.068079557
• Heavy Atom Count: 12
• Complexity: 182

Purity/Quality:

98% ^*data from raw suppliers

rel-(1R,2S)-2-PhenylcyclopropanecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C1C(=O)O)C2=CC=CC=C2
• Isomeric SMILES: C1[C@H]([C@H]1C(=O)O)C2=CC=CC=C2
• Uses: rel-(1R,2S)-2-Phenylcyclopropanecarboxylic Acid is a reagent used in the synthesis of tranylcypromine compounds which are potent and efficacious 5-HT2C receptor agonists.

Technology Process of (1S,2R)-2-Phenylcyclopropanecarboxylic acid

There total 29 articles about (1S,2R)-2-Phenylcyclopropanecarboxylic acid 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: 91.0%

cis-1-ethoxycarbonyl-2-phenylcyclopropane (946-38-3) → (1S*,2R*)-2-phenylcyclopropane-1-carboxylic acid (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)

Guidance literature:

With ethanol; potassium hydroxide; at 20 ℃;

DOI:10.1021/ja101557k

Reference yield: 77.0%

iodoform (75-47-8) + cis-cinnamic acid (140-10-3,621-82-9,102-94-3) → (1S*,2R*)-2-phenylcyclopropane-1-carboxylic acid (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)

Guidance literature:

With samarium; In tetrahydrofuran; for 1h; sonication;

DOI:10.1021/ol0709174

Reference yield: 71.0%

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) → (1S*,2R*)-2-phenylcyclopropane-1-carboxylic acid (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) + trans-2-phenylcyclopropane-1-carboxylic acid (939-90-2)

Guidance literature:

With sodium hydroxide; In ethanol;

upstream raw materials:

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

((R)-2-Phenyl-cyclopropyl)-methanol

(1R,2S)-1,2-di(hydroxymethyl)-2-phenylcyclopropane

styrene

Downstream raw materials:

(1S,2S)-2-phenylcyclopropanecarboxylic acid methyl ester

(1S,2R)-2-phenylcyclopropanecarboxylic acid methyl ester

cis-methyl 2-phenylcyclopropane-1-carboxylate

((1R,4aS)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methanaminium (1R,2S)-2-phenylcyclopropane-1-carboxylate

Refernces

• 1、 Ladd, Carolyn L.,Sustac Roman, Daniela,Charette, André B.. "Silver-promoted, palladium-catalyzed direct arylation of cyclopropanes: Facile access to spiro 3,3′-cyclopropyl oxindoles". supporting information. p. 1350 - 1353. Retrieved 2013/05/09.
• 2、 Cheng, Kejun,Lee, Yong Sok,Rothman, Richard B.,Dersch, Christina M.,Bittman, Ross W.,Jacobson, Arthur E.,Rice, Kenner C.. "Probes for narcotic receptor mediated phenomena. 41. Unusual inverse μ-agonists and potent μ-opioid antagonists by modification of the N-substituent in enantiomeric 5-(3-hydroxyphenyl)morphans". experimental part. p. 957 - 969. Retrieved 2011/04/24.