(S)-2-Phenylpyrrolidine

Base Information

• Chemical Name: (S)-2-Phenylpyrrolidine
• CAS No.: 59347-91-0
• Molecular Formula: C₁₀H₁₃N
• Molecular Weight: 147.22
• Hs Code.: 2933998090
• DSSTox Substance ID: DTXSID00364078
• Nikkaji Number: J398.015D
• Wikidata: Q72498604
• Mol file: 59347-91-0.mol

Synonyms:(S)-2-PHENYLPYRROLIDINE;59347-91-0;(2S)-2-phenylpyrrolidine;Pyrrolidine, 2-phenyl-, (2S)-;MFCD06762549;SCHEMBL170704;DTXSID00364078;AM9385;AKOS015933309;CS-W021168;DS-6028;TS-01936;EN300-2991215;A850147;J-502431

Chemical Property of (S)-2-Phenylpyrrolidine

Chemical Property:

• Vapor Pressure: 0.0459mmHg at 25°C
• Boiling Point: 237oC at 760 mmHg
• PKA: 10.13±0.10(Predicted)
• Flash Point: 98.3oC
• PSA: 12.03000
• Density: 0.988g/cm3
• LogP: 2.43990
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 147.104799419
• Heavy Atom Count: 11
• Complexity: 116

Purity/Quality:

99% ^*data from raw suppliers

(S)-2-Phenylpyrrolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(NC1)C2=CC=CC=C2
• Isomeric SMILES: C1C[C@H](NC1)C2=CC=CC=C2
• Description: (S)-2-Phenylpyrrolidine is an amine that has been synthesized for use in research. It is chiral and can exist as either the levorotatory or dextrorotatory form. It interacts with the tropomyosin receptor, which is a protein found on the surface of muscle cells. This interaction prevents calcium ions from binding to tropomyosin, thereby preventing muscle contraction.
• Uses: (S)-2-Phenylpyrrolidine has been shown to be effective in treating neurodegenerative diseases such as Alzheimer's disease and Parkinson's disease. Research also suggests that this drug may be effective at preventing aldehyde toxicity mediated by the enzyme acetaldehyde dehydrogenase 2 (ALDH2).

Technology Process of (S)-2-Phenylpyrrolidine

There total 41 articles about (S)-2-Phenylpyrrolidine 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: 99.0%

(-)-(S)-2-Phenylpyrrolidine hydrochloride (56523-58-1) → (S)-2-phenylpyrrolidine (1006-64-0,56523-47-8,56586-11-9,59347-91-0)

Guidance literature:

With sodium hydrogencarbonate; In diethyl ether; at 20 ℃; for 0.166667h; optical yield given as %ee;

DOI:10.1039/b925209f

Reference yield: 99.0%

(S)-1-((S)-2-methyl-propane-2-sulfinyl)-2-phenyl-pyrrolidine (1207729-66-5) → (S)-2-phenylpyrrolidine (1006-64-0,56523-47-8,56586-11-9,59347-91-0)

Guidance literature:

(S)-1-((S)-2-methyl-propane-2-sulfinyl)-2-phenyl-pyrrolidine; With hydrogenchloride; In 1,4-dioxane; methanol; at 20 ℃; for 0.5h; Inert atmosphere;

With sodium hydroxide; In water; pH=13;

DOI:10.1039/b917435d

Reference yield: 98.0%

tert-butyl (4-oxo-4-phenyl-butyl)-carbamate (116437-41-3) → (S)-2-phenylpyrrolidine (1006-64-0,56523-47-8,56586-11-9,59347-91-0)

Guidance literature:

tert-butyl (4-oxo-4-phenyl-butyl)-carbamate; With trifluoroacetic acid; In dichloromethane; for 3h; Inert atmosphere; Schlenk technique;

With 1,4-diaza-bicyclo[2.2.2]octane; titanium(IV) isopropylate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; (2R)-1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-[bis[4-(trifluoromethyl)phenyl]phosphino]ferrocene; hydrogen; potassium iodide; In tetrahydrofuran; toluene; at 50 ℃; for 13h; under 38002.6 Torr; Solvent; enantioselective reaction; Autoclave;

DOI:10.1055/s-0037-1611533

upstream raw materials:

(+)-N-<2-(2(R)-Phenyl-1-(phenylthio)ethyl)>-5(S)-phenyl-2-pyrrolidine

diphenyldisulfane

2-phenyl-1-pyrroline

2-phenylpyrrolidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

(S)-(-)-1-methyl-2-phenylpyrrolidine

C₂₇H₃₅N

C₁₀H₁₁N

2,2,2-Trifluoro-1-((S)-2-phenyl-pyrrolidin-1-yl)-ethanone

Refernces

• 1、 Fanourakis, Alexander,Paterson, Kieran J.,Phipps, Robert J.,Williams, Benjamin D.. "Enantioselective Intermolecular C-H Amination Directed by a Chiral Cation". supporting information. p. 10070 - 10076. Retrieved 2021/07/21.
• 2、 Wu, Shuke,Zhou, Yi,Rebelein, Johannes G.,Kuhn, Miriam,Mallin, Hendrik,Zhao, Jingming,Igareta, Nico V.,Ward, Thomas R.. "Breaking Symmetry: Engineering Single-Chain Dimeric Streptavidin as Host for Artificial Metalloenzymes". supporting information. p. 15869 - 15878. Retrieved 2019/10/11.