4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl]but-3-yn-2-one

Base Information

• Chemical Name: 4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl]but-3-yn-2-one
• CAS No.: 224631-90-7
• Molecular Formula: C₁₃H₁₈O₂
• Molecular Weight: 206.285
• Mol file: 224631-90-7.mol

Synonyms:4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl]but-3-yn-2-one

Chemical Property of 4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl]but-3-yn-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl]but-3-yn-2-one

There total 6 articles about 4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl]but-3-yn-2-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: 99.0%

4-({(4R)-4-[(1,1-dimethylethyl)dimethylsilyl]oxy}-2,6,6-trimethylcyclohex-1-enyl)but-3-yn-2-one (322474-87-3) → 4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl]but-3-yn-2-one (224631-90-7)

Guidance literature:

With hydrogen fluoride;

DOI:10.1248/cpb.48.2017

Reference yield:

citroside A <(5-dehydroxygrasshopper ketone-5-yl) 5-β-D-glucopyranoside> (120330-44-1) → 4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl]but-3-yn-2-one (224631-90-7)

Guidance literature:

With β-glucosidase; In water; at 37 ℃; for 24h; pH=5.5; Enzymatic reaction;

DOI:10.1021/jf9807364

Reference yield:

(R)-4-ethynyl-3,5,5-trimethylcyclohex-3-en-1-ol (118829-40-6,118829-45-1) → 4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl]but-3-yn-2-one (224631-90-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 99 percent / DMAP; Et₃N / CH₂Cl₂ / 1.5 h / 20 °C

2.1: BuLi / hexane; tetrahydrofuran / 0.25 h / -40 °C

2.2: hexane; tetrahydrofuran / 0.42 h / -40 - 20 °C

3.1: 4.82 g / MnO₂ / diethyl ether; hexane / 15 h / 20 °C

4.1: 99 percent / aq, HF / acetonitrile / 0.5 h / 20 °C

With dmap; manganese(IV) oxide; n-butyllithium; hydrogen fluoride; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetonitrile;

DOI:10.1039/b208758h

upstream raw materials:

citroside A <(5-dehydroxygrasshopper ketone-5-yl) 5-β-D-glucopyranoside>

4-({(4R)-4-[(1,1-dimethylethyl)dimethylsilyl]oxy}-2,6,6-trimethylcyclohex-1-enyl)but-3-yn-2-one

(R)-4-ethynyl-3,5,5-trimethylcyclohex-3-en-1-ol

1,1-dimethylethyl{[(1R)-4-ethynyl-3,5,5-trimethylcyclohex-3-entl]oxy}dimethylsilane

Downstream raw materials:

3-hydroxymegastigma-5,8-dien-7-one

Damascenon

2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[(S)-3-((R)-4-acetoxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-methyl-prop-2-ynyloxy]-3,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester

2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[(R)-3-((R)-4-acetoxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-methyl-prop-2-ynyloxy]-3,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester