6-[3'-hydroxy-4'-methylpent-4'-en-1'-yl]-3-methoxycyclohex-2-en-1-one

Base Information

• Chemical Name: 6-[3'-hydroxy-4'-methylpent-4'-en-1'-yl]-3-methoxycyclohex-2-en-1-one
• CAS No.: 1312767-99-9
• Molecular Formula: C₁₃H₂₀O₃
• Molecular Weight: 224.3
• Mol file: 1312767-99-9.mol

Synonyms:6-[3'-hydroxy-4'-methylpent-4'-en-1'-yl]-3-methoxycyclohex-2-en-1-one

Chemical Property of 6-[3'-hydroxy-4'-methylpent-4'-en-1'-yl]-3-methoxycyclohex-2-en-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-[3'-hydroxy-4'-methylpent-4'-en-1'-yl]-3-methoxycyclohex-2-en-1-one

There total 4 articles about 6-[3'-hydroxy-4'-methylpent-4'-en-1'-yl]-3-methoxycyclohex-2-en-1-one 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: 96.0%

6-[3'-[(tert-butyldimethylsilyl)oxy]-4'-methylpent-4'-en-1-yl]-3-methoxycyclohex-2-en-1-one (1312768-01-6) → 6-[3'-hydroxy-4'-methylpent-4'-en-1'-yl]-3-methoxycyclohex-2-en-1-one (1312767-99-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 - 50 ℃; for 3h;

DOI:10.1021/ol2013439

Reference yield:

(3RS)-3-[(tert-butyldimethylsilyl)oxy]-4-methylpent-4-en-1-ol → 6-[3'-hydroxy-4'-methylpent-4'-en-1'-yl]-3-methoxycyclohex-2-en-1-one (1312767-99-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1H-imidazole; iodine; triphenylphosphine / tetrahydrofuran / 0 - 20 °C

2.1: n-butyllithium; diisopropylamine / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane / 1.25 h / -78 - 0 °C

2.2: 10.25 h / -78 - -40 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 - 50 °C

With 1H-imidazole; n-butyllithium; tetrabutyl ammonium fluoride; iodine; diisopropylamine; triphenylphosphine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane;

DOI:10.1021/ol2013439

Reference yield:

(3RS)-5-[(4-methoxyphenyl)methoxy]-2-methylpent-1-en-3-ol (1312768-11-8) → 6-[3'-hydroxy-4'-methylpent-4'-en-1'-yl]-3-methoxycyclohex-2-en-1-one (1312767-99-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 20 °C

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 20 °C / pH 7 / phosphate buffer; Cooling with ice

3.1: 1H-imidazole; iodine; triphenylphosphine / tetrahydrofuran / 0 - 20 °C

4.1: n-butyllithium; diisopropylamine / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane / 1.25 h / -78 - 0 °C

4.2: 10.25 h / -78 - -40 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 - 50 °C

With 1H-imidazole; n-butyllithium; tetrabutyl ammonium fluoride; iodine; diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol2013439

upstream raw materials:

6-[3'-[(tert-butyldimethylsilyl)oxy]-4'-methylpent-4'-en-1-yl]-3-methoxycyclohex-2-en-1-one

(3RS)-5-[(4-methoxyphenyl)methoxy]-2-methylpent-1-en-3-ol

(3RS)-tert-butyl{5-[(4-methoxyphenyl)methoxy]-2-methylpent-1-en-3-yloxy}dimethylsilane

Downstream raw materials:

(±)-platencin

2-(2'-bromoprop-2'-en-1'-yl)-6-[3''-hydroxy-4''-methylpent-4''-en-1''-yl]-3-methoxycyclohex-2-en-1-one

C₂₀H₂₈O₃

6-(3-hydroxy-4-methylpentyl)-3-methoxycyclohex-2-enone