trans-4-Phenyl-L-proline

Base Information

• Chemical Name: trans-4-Phenyl-L-proline
• CAS No.: 96314-26-0
• Molecular Formula: C11H13NO2
• Molecular Weight: 191.23
• Hs Code.: 2933990090
• European Community (EC) Number: 416-020-1
• ChEMBL ID: CHEMBL4084026
• DSSTox Substance ID: DTXSID40510299
• Wikidata: Q72498367
• Mol file: 96314-26-0.mol

Synonyms:96314-26-0;(2S,4S)-4-PHENYLPYRROLIDINE-2-CARBOXYLIC ACID;trans-4-Phenyl-L-proline;(4S)-4-Phenyl-L-proline;L-Proline, 4-phenyl-, trans-;EC 416-020-1;(trans)-4-phenyl-L-proline;SCHEMBL124005;CHEMBL4084026;DTXSID40510299;JHHOFXBPLJDHOR-ZJUUUORDSA-N;AKOS006286465;AKOS016015828;HY-W067473;AS-66731;CS-0059274;A26659;EN300-214558;F11095;(2s,4s)-4-phenyl-pyrrolidine-2-carboxylic acid

Chemical Property of trans-4-Phenyl-L-proline

Chemical Property:

• Vapor Pressure: 3.22E-06mmHg at 25°C
• Melting Point: >300 °C (decomp)
• Refractive Index: 1.562
• Boiling Point: 372.8 °C at 760 mmHg
• PKA: 2.25±0.40(Predicted)
• Flash Point: 179.3 °C
• PSA: 49.33000
• Density: 1.186 g/cm³
• LogP: 1.54550
• Storage Temp.: 2-8°C
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 191.094628657
• Heavy Atom Count: 14
• Complexity: 211

Purity/Quality:

98% ^*data from raw suppliers

L-Proline,4-phenyl-,(4S)- 98 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 43-62
• Safety Statements: 22-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(CNC1C(=O)O)C2=CC=CC=C2
• Isomeric SMILES: C1[C@H](CN[C@@H]1C(=O)O)C2=CC=CC=C2

Technology Process of trans-4-Phenyl-L-proline

There total 19 articles about trans-4-Phenyl-L-proline 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: 67.0%

(2S,4S)-1-Benzoyl-4-phenyl-pyrrolidine-2-carboxylic acid (120851-71-0) → trans-4-phenyl-L-proline (96314-26-0)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 12h; Inert atmosphere; Reflux;

Reference yield:

1-benzyloxycarbonyl-4-keto-L-proline (64187-47-9) → trans-4-phenyl-L-proline (96314-26-0)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / 18 h / Ambient temperature

2: 91 percent / CH₂Cl₂; trifluoroacetic acid / 18 h

3: 1.) Li, 2.) CH₃COOH / 1.) ammonium, -78 deg C, 10 min, 2.) 2 h

With lithium; acetic acid; In tetrahydrofuran; dichloromethane; trifluoroacetic acid;

DOI:10.1021/jm00401a014

Reference yield:

phenylmagnesium bromide → trans-4-phenyl-L-proline (96314-26-0)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / 18 h / Ambient temperature

2: 91 percent / CH₂Cl₂; trifluoroacetic acid / 18 h

3: 1.) Li, 2.) CH₃COOH / 1.) ammonium, -78 deg C, 10 min, 2.) 2 h

With lithium; acetic acid; In tetrahydrofuran; dichloromethane; trifluoroacetic acid;

DOI:10.1021/jm00401a014

upstream raw materials:

3-chloro-5-phenyl-piperidin-2-one

ethanol

water

5-phenylpiperidin-2-one

Downstream raw materials:

(2S,4S)-1-(tert-butoxycarbonyl)-4-phenyl-2-pyrrolidinecarboxylic acid

(2S,4S)-4-cyclohexylpyrrolidine-2-carboxylic acid

fosinopril

trans-1-{[hydroxy(4-phenylbutyl)phosphinyl]acetyl}-4-phenyl-L-proline

Refernces

• 1、 Ibrahim, Mohamed A.,Johnson, Henry W. B.,Jeong, Joon Won,Lewis, Gary L.,Shi, Xian,Noguchi, Robin T.,Williams, Matthew,Leahy, James W.,Nuss, John M.,Woolfrey, John,Banica, Monica,Bentzien, Frauke,Chou, Yu-Chien,Gibson, Anna,Heald, Nathan,Lamb, Peter,Mattheakis, Larry,Matthews, David,Shipway, Aaron,Wu, Xiang,Zhang, Wentao,Zhou, Sihong,Shankar, Geetha. "Discovery of a novel class of potent and orally bioavailable sphingosine 1-phosphate receptor 1 antagonists". experimental part. p. 1368 - 1381. Retrieved 2012/04/04.
• 2、 Thottathil, John K.,Moniot, Jerome L.. "LITHIUM DIPHENYLCUPRATE REACTIONS WITH 4-TOSYLOXY-L-PROLINES; AN INTERESTING STEREOCHEMICAL OUTCOME. A SYNTHESIS OF TRANS-4-PHENYL-L-PROLINE.". . p. 151 - 154. Retrieved 2007/10/02.