(4S,5R)-5-(3-chloroprop-1-en-2-yl)-4-hydroxy-2-methylcyclohex-2-enone

Base Information

• Chemical Name: (4S,5R)-5-(3-chloroprop-1-en-2-yl)-4-hydroxy-2-methylcyclohex-2-enone
• CAS No.: 1376709-08-8
• Molecular Formula: C₁₀H₁₃ClO₂
• Molecular Weight: 200.665
• Mol file: 1376709-08-8.mol

Synonyms:(4S,5R)-5-(3-chloroprop-1-en-2-yl)-4-hydroxy-2-methylcyclohex-2-enone

Chemical Property of (4S,5R)-5-(3-chloroprop-1-en-2-yl)-4-hydroxy-2-methylcyclohex-2-enone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-5-(3-chloroprop-1-en-2-yl)-4-hydroxy-2-methylcyclohex-2-enone

There total 1 articles about (4S,5R)-5-(3-chloroprop-1-en-2-yl)-4-hydroxy-2-methylcyclohex-2-enone 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: 64.0%

(4S,5R)-4-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone (90129-47-8) → (4S,5R)-5-(3-chloroprop-1-en-2-yl)-4-hydroxy-2-methylcyclohex-2-enone (1376709-08-8)

Guidance literature:

With calcium hypochlorite; In dichloromethane; water; for 2h; regioselective reaction; Cooling with ice;

DOI:10.1021/ja303529z

Reference yield: 78.0%

(4S,5R)-5-(3-chloroprop-1-en-2-yl)-4-hydroxy-2-methylcyclohex-2-enone (1376709-08-8) + acetic acid (64-19-7,77671-22-8) → (1R,6R)-6-(3-chloroprop-1-en-2-yl)-3-methyl-4-oxocyclohex-2-enyl acetate

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In diethyl ether; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b01797

Reference yield: 70.0%

formic acid (64-18-6) + (4S,5R)-5-(3-chloroprop-1-en-2-yl)-4-hydroxy-2-methylcyclohex-2-enone (1376709-08-8) → (1R,6R)-6-(3-chloroprop-1-en-2-yl)-3-methyl-4-oxocyclohex-2-en-1-yl formate (1376709-10-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ja303529z

upstream raw materials:

(4S,5R)-4-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone

Downstream raw materials:

(1R,6R)-6-(3-chloroprop-1-en-2-yl)-3-methyl-4-oxocyclohex-2-en-1-yl formate

(4aR,6R,8aR)-6-((tert-butyldimethylsilyl)oxy)-4-(((4-methoxybenzyl)oxy)methyl)-7-methyl-4a,5,6,8a-tetrahydro-2H-chromen-2-one

(1R,4R,6R)-6-(3-chloroprop-1-en-2-yl)-4-hydroxy-3-methylcyclohex-2-en-1-yl formate

C₃₃H₄₄O₅