cis-1,3-Dimethyl-4-ethynyl-6-(2-methylphenyl)-3,4-piperidinediol

Base Information

• Chemical Name: cis-1,3-Dimethyl-4-ethynyl-6-(2-methylphenyl)-3,4-piperidinediol
• CAS No.: 120729-77-3
• Molecular Formula: C16H21 N O2
• Molecular Weight: 259.3434
• DSSTox Substance ID: DTXSID70152984
• Wikidata: Q76279501
• Mol file: 120729-77-3.mol

Synonyms:BRN 3552851;3,4-Piperidinediol, 1,3-dimethyl-4-ethynyl-6-(2-methylphenyl)-, (3-alpha,4-beta,6-beta)-;cis-1,3-Dimethyl-4-ethynyl-6-(2-methylphenyl)-3,4-piperidinediol;(3-alpha,4-beta,6-beta)-1,3-Dimethyl-4-ethynyl-6-(2-methylphenyl)-3,4-piperidinediol;120729-77-3;DTXSID70152984;LS-115167

Chemical Property of cis-1,3-Dimethyl-4-ethynyl-6-(2-methylphenyl)-3,4-piperidinediol

Chemical Property:

• Vapor Pressure: 1.84E-06mmHg at 25°C
• Boiling Point: 380.3°C at 760 mmHg
• Flash Point: 176.9°C
• Density: 1.16g/cm³
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 259.157228913
• Heavy Atom Count: 19
• Complexity: 388

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CC=C1C2CC(C(CN2C)(C)O)(C#C)O
• Isomeric SMILES: CC1=CC=CC=C1[C@@H]2C[C@]([C@@](CN2C)(C)O)(C#C)O

Technology Process of cis-1,3-Dimethyl-4-ethynyl-6-(2-methylphenyl)-3,4-piperidinediol

There total 2 articles about cis-1,3-Dimethyl-4-ethynyl-6-(2-methylphenyl)-3,4-piperidinediol 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%

(2R,5R)-5-Hydroxy-1,5-dimethyl-2-o-tolyl-piperidin-4-one (60053-95-4,120729-70-6) + sodium acetylide (1066-26-8) → 3e,4e-dihydroxy-1e,3a-dimethyl-6e-(2-tolyl)-4a-ethynylpiperidine (120729-77-3)

Guidance literature:

In diethyl ether; ammonia; for 1h;

DOI:10.1007/BF00764463

Reference yield:

(E)-1-(2-Methyl-oxiranyl)-3-o-tolyl-propenone (120729-68-2) → 3e,4e-dihydroxy-1e,3a-dimethyl-6e-(2-tolyl)-4a-ethynylpiperidine (120729-77-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / propan-2-ol / 20 °C

2: 86 percent / liquid ammonia / diethyl ether / 1 h

With ammonia; In diethyl ether; isopropyl alcohol;

DOI:10.1007/BF00766856

Reference yield: 92.0%

3e,4e-dihydroxy-1e,3a-dimethyl-6e-(2-tolyl)-4a-ethynylpiperidine (120729-77-3) → 3e,4e-dihydroxy-1e,3a-dimethyl-6e-(2-tolyl)-4a-ethylpiperidine (128887-79-6)

Guidance literature:

With hydrogen; platinum; In methanol;

DOI:10.1007/BF00766856

upstream raw materials:

(2R,5R)-5-Hydroxy-1,5-dimethyl-2-o-tolyl-piperidin-4-one

sodium acetylide

(E)-1-(2-Methyl-oxiranyl)-3-o-tolyl-propenone

Downstream raw materials:

3e,4e-dihydroxy-1e,3a-dimethyl-6e-(2-tolyl)-4a-ethylpiperidine

Refernces

• 1、 Zakharevskii,Zvonok,Lugovskii,Melentovich,Stanishevskii,Yushkevich. "Synthesis and pharmacological activity of acetylenic piperidinediols". . p. 140 - 143. Retrieved 2007/10/02.