2-Cyclohexen-1-one, 3-ethynyl-5-hydroxy-2-methyl-, (R)- (9CI)

Base Information

• Chemical Name: 2-Cyclohexen-1-one, 3-ethynyl-5-hydroxy-2-methyl-, (R)- (9CI)
• CAS No.: 169305-41-3
• Molecular Formula: C9H10 O2
• Molecular Weight: 150.1745
• Mol file: 169305-41-3.mol

Synonyms:2-Cyclohexen-1-one, 3-ethynyl-5-hydroxy-2-methyl-, (R)- (9CI)

Chemical Property of 2-Cyclohexen-1-one, 3-ethynyl-5-hydroxy-2-methyl-, (R)- (9CI)

Chemical Property:

• Boiling Point: 252.9±40.0 °C(Predicted)
• PKA: 13.42±0.60(Predicted)
• PSA: 37.30000
• Density: 1.13±0.1 g/cm3(Predicted)
• LogP: 0.65990

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Cyclohexen-1-one, 3-ethynyl-5-hydroxy-2-methyl-, (R)- (9CI)

There total 1 articles about 2-Cyclohexen-1-one, 3-ethynyl-5-hydroxy-2-methyl-, (R)- (9CI) 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: 82.0%

(3S,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene (113375-51-2) → (5R)-3-Ethynyl-5-hydroxy-2-methyl-2-cyclohexen-1-one (169305-41-3)

Guidance literature:

With Dess-Martin periodane; In acetonitrile; for 1h; Ambient temperature;

DOI:10.1021/jo00124a014

Reference yield: 68.0%

(5R)-3-Ethynyl-5-hydroxy-2-methyl-2-cyclohexen-1-one (169305-41-3) → (3S,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene (113375-51-2) + (3R,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene (169437-97-2)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 0.5h;

DOI:10.1021/jo00124a014

Reference yield:

(5R)-3-Ethynyl-5-hydroxy-2-methyl-2-cyclohexen-1-one (169305-41-3) → Chloro-acetic acid (1R,5R)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / NaBH₄ / methanol / 0.5 h

2: 2.5 percent / tetrahydrofuran / 92 h / Ambient temperature; Chromobacterium viscosum lipase

With sodium tetrahydroborate; In tetrahydrofuran; methanol;

DOI:10.1021/jo00124a014

upstream raw materials:

(3S,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene

Downstream raw materials:

(3S,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene

(3R,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene

(1S,5R)-5-acetoxy-1-ethynyl-3-hydroxy-2-methylcyclohex-1-ene

(3R,5R)-3,5-diacetoxy-1-ethynyl-2-methylcyclohex-1-ene

Refernces