(-)-(1S)-1-[(6,6-dimethyl-1-cyclohexen-1-yl)methyl]-2-propynyl pivalate

Base Information

• Chemical Name: (-)-(1S)-1-[(6,6-dimethyl-1-cyclohexen-1-yl)methyl]-2-propynyl pivalate
• CAS No.: 899421-04-6
• Molecular Formula: C₁₇H₂₆O₂
• Molecular Weight: 262.392
• Mol file: 899421-04-6.mol

Synonyms:(-)-(1S)-1-[(6,6-dimethyl-1-cyclohexen-1-yl)methyl]-2-propynyl pivalate

Chemical Property of (-)-(1S)-1-[(6,6-dimethyl-1-cyclohexen-1-yl)methyl]-2-propynyl pivalate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1S)-1-[(6,6-dimethyl-1-cyclohexen-1-yl)methyl]-2-propynyl pivalate

There total 7 articles about (-)-(1S)-1-[(6,6-dimethyl-1-cyclohexen-1-yl)methyl]-2-propynyl pivalate 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: 85.0%

(-)-(1S)-1-[(6,6-dimethyl-1-cyclohexen-1-yl)methyl]-4-hydroxy-4-methyl-2-pentynyl pivalate (1197241-07-8) → (-)-(1S)-1-[(6,6-dimethyl-1-cyclohexen-1-yl)methyl]-2-propynyl pivalate (899421-04-6)

Guidance literature:

With 18-crown-6 ether; potassium carbonate; In toluene; for 24h; optical yield given as %ee; Reflux;

DOI:10.1002/chem.200901292

Reference yield:

(S)-1-(6,6-Dimethyl-cyclohex-1-enyl)-but-3-yn-2-ol + pivaloyl chloride (3282-30-2) → (-)-(1S)-1-[(6,6-dimethyl-1-cyclohexen-1-yl)methyl]-2-propynyl pivalate (899421-04-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1002/anie.200504543

Reference yield:

(6,6-dimethyl-1-cyclohexen-1-yl)-acetaldehyde (408524-50-5) → (-)-(1S)-1-[(6,6-dimethyl-1-cyclohexen-1-yl)methyl]-2-propynyl pivalate (899421-04-6)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 0.75 h / 25 - 28 °C

2: 4-(N,N-dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 2 h / 0 °C

With dmap; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1002/anie.200504543

upstream raw materials:

pivaloyl chloride

(6,6-dimethyl-1-cyclohexen-1-yl)-acetaldehyde

2-(6,6-dimethylcyclohex-1-en-1-yl)ethan-1-ol

2,2-dimethyl-cyclohexanone