Vesamicol

Base Information

• Chemical Name: Vesamicol
• CAS No.: 112709-59-8
• Molecular Formula: C17H25 N O
• Molecular Weight: 259.392
• UNII: I1A877466V,3D416V0FLM
• DSSTox Substance ID: DTXSID20920872
• Nikkaji Number: J404.506H
• Wikipedia: Vesamicol
• Pharos Ligand ID: RY2KT1NT8L3W
• ChEMBL ID: CHEMBL20730
• Mol file: 112709-59-8.mol

Synonyms:2-(4-phenyl-1-piperidinyl)cyclohexanol;2-(4-phenylpiperidino)cyclohexanol;AH 5183;AH-5183;methylvesamicol;vesamicol;vesamicol hydrochloride;vesamicol hydrochloride, (+,-)-;vesamicol, (+,-)-

Chemical Property of Vesamicol

Chemical Property:

• Vapor Pressure: 6.73E-07mmHg at 25°C
• Melting Point: 238.5-240.0 °C
• Boiling Point: 393.5°Cat760mmHg
• PKA: 15.16±0.40(Predicted)
• Flash Point: 97°C
• PSA: 23.47000
• Density: 1.086g/cm³
• LogP: 3.90940
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 259.193614421
• Heavy Atom Count: 19
• Complexity: 266

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(C(C1)N2CCC(CC2)C3=CC=CC=C3)O
• Isomeric SMILES: C1CC[C@H]([C@@H](C1)N2CCC(CC2)C3=CC=CC=C3)O

Technology Process of Vesamicol

There total 4 articles about Vesamicol 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: 97.0%

(1R,2R)-2-(4-phenyl-1,2,5,6-tetrahydropyridin-1-yl)cyclohexanol → (-)-vesamicol (112709-59-8,112709-60-1,22232-64-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 12h;

DOI:10.1016/j.tetasy.2004.03.002

Reference yield: 43.0%

vinyl acetate (108-05-4,9003-20-7) + (+/-)-(1S,2S)-2-(4-phenylpiperidin-1-yl)cyclohexanol (112709-60-1,22232-64-0) → (-)-vesamicol (112709-59-8,112709-60-1,22232-64-0) + (+)-Vesamicol (112709-60-1,22232-64-0) + (1R,2R)-2-(4-phenylpiperidin-1-yl)cyclohexyl acetate

Guidance literature:

With Pseudomonas cepacia lipase; In various solvent(s); at 28 ℃; for 29h; Enzymatic reaction;

DOI:10.1016/j.tetasy.2004.03.002

Reference yield:

4-phenylpiperidine (771-99-3) + cyclohexane-1,2-epoxide (286-20-4) → (-)-vesamicol (112709-59-8,112709-60-1,22232-64-0) + (+)-Vesamicol (112709-60-1,22232-64-0)

Guidance literature:

In ethanol; for 22h; Yield given; Heating;

DOI:10.1021/jm00126a013

upstream raw materials:

4-phenylpiperidine

cyclohexane-1,2-epoxide

vinyl acetate

(+/-)-(1S,2S)-2-(4-phenylpiperidin-1-yl)cyclohexanol

Downstream raw materials:

(1R,2R)-2-[4-(4-Amino-phenyl)-piperidin-1-yl]-cyclohexanol

Refernces

• 1、 Gonzalez-Sabin, Javier,Gotor, Vicente,Rebolledo, Francisca. "Chemoenzymatic preparation of optically active β-amino-cyclohexanols and their application in the enantioselective addition of diethylzinc to benzaldehyde". . p. 1335 - 1341. Retrieved 2007/10/03.