3-methyl-2-thiomethyl-5-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-2,4-pentadienenitrile

Base Information

• Chemical Name: 3-methyl-2-thiomethyl-5-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-2,4-pentadienenitrile
• CAS No.: 330808-35-0
• Molecular Formula: C₁₆H₂₃NS
• Molecular Weight: 261.431
• Mol file: 330808-35-0.mol

Synonyms:3-methyl-2-thiomethyl-5-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-2,4-pentadienenitrile

Chemical Property of 3-methyl-2-thiomethyl-5-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-2,4-pentadienenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-methyl-2-thiomethyl-5-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-2,4-pentadienenitrile

There total 2 articles about 3-methyl-2-thiomethyl-5-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-2,4-pentadienenitrile 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: 97.0%

methyl thiocyanate (556-64-9) + (2E,4E)-3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienenitrile (5299-98-9) → 3-methyl-2-thiomethyl-5-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-2,4-pentadienenitrile (330808-35-0)

Guidance literature:

With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -85 ℃;

DOI:10.1021/jo0009595

Reference yield:

(E)-β-ionone (79-77-6,14901-07-6) → 3-methyl-2-thiomethyl-5-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-2,4-pentadienenitrile (330808-35-0)

Guidance literature:

Multi-step reaction with 2 steps

1: BuLi / tetrahydrofuran; hexane / 2 h / -80 - 20 °C

2: 97 percent / i-Pr₂NH; BuLi / tetrahydrofuran; hexane / -85 °C

With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; 1: Horner-Emmonds reaction;

DOI:10.1021/jo0009595

Reference yield: 34.0%

3-methyl-2-thiomethyl-5-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-2,4-pentadienenitrile (330808-35-0) → 3-methyl-2-thiomethyl-5-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-2,4-pentadienal (330808-37-2)

Guidance literature:

With diisobutylaluminium hydride; In hexane; Petroleum ether; at -50 ℃; for 0.333333h;

DOI:10.1021/jo0009595

upstream raw materials:

methyl thiocyanate

(2E,4E)-3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienenitrile

(E)-β-ionone

Downstream raw materials:

3-methyl-2-thiomethyl-5-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-2,4-pentadienal