(5R)-5-isopropenyl-2-methyl-1-trimethyl-silanyloxy-cyclohex-2-ene-1-carbonitrile

Base Information

• Chemical Name: (5R)-5-isopropenyl-2-methyl-1-trimethyl-silanyloxy-cyclohex-2-ene-1-carbonitrile
• CAS No.: 332920-11-3
• Molecular Formula: C₁₄H₂₃NOSi
• Molecular Weight: 249.428
• Mol file: 332920-11-3.mol

Synonyms:(5R)-5-isopropenyl-2-methyl-1-trimethyl-silanyloxy-cyclohex-2-ene-1-carbonitrile

Chemical Property of (5R)-5-isopropenyl-2-methyl-1-trimethyl-silanyloxy-cyclohex-2-ene-1-carbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R)-5-isopropenyl-2-methyl-1-trimethyl-silanyloxy-cyclohex-2-ene-1-carbonitrile

There total 3 articles about (5R)-5-isopropenyl-2-methyl-1-trimethyl-silanyloxy-cyclohex-2-ene-1-carbonitrile 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: 94.0%

trimethylsilyl cyanide (7677-24-9) + (R)-Carvone (6485-40-1,2244-16-8) → (5R)-5-isopropenyl-2-methyl-1-trimethyl-silanyloxy-cyclohex-2-ene-1-carbonitrile (332920-11-3)

Guidance literature:

With n-butyllithium; triethylene glucol monomethyl ether; In tetrahydrofuran; at 22 ℃; for 4h;

DOI:10.1021/ol0069608

Reference yield:

chloro-trimethyl-silane (75-77-4) + (R)-Carvone (6485-40-1,2244-16-8) + sodium cyanide (143-33-9,25596-52-5) → C14H23NOSi + (5R)-5-isopropenyl-2-methyl-1-trimethyl-silanyloxy-cyclohex-2-ene-1-carbonitrile (332920-11-3)

Guidance literature:

In hexane; dimethyl sulfoxide; at 60 ℃; for 0.0833333h;

DOI:10.1021/jo702587e

Reference yield:

(4R,6R)-carveol (99-48-9,1197-06-4,1197-07-5,2102-58-1,2102-59-2,5157-78-8,5503-11-7,7632-16-8,18383-51-2,22567-18-6,20307-86-2) → (5R)-5-isopropenyl-2-methyl-1-trimethyl-silanyloxy-cyclohex-2-ene-1-carbonitrile (332920-11-3)

Guidance literature:

Multi-step reaction with 2 steps

1: chromium(VI) oxide; acetic anhydride / dichloromethane / 0.33 h / -55 °C

2: L-proline lithium salt / 24 h / 20 °C

With chromium(VI) oxide; acetic anhydride; L-proline lithium salt; In dichloromethane; 1: Dauben-Michno oxidation;

DOI:10.1139/v11-026

upstream raw materials:

trimethylsilyl cyanide

(R)-Carvone

chloro-trimethyl-silane

sodium cyanide

Downstream raw materials:

(S)-p-mentha-6,8-dien-2-one

carvotanacetone

(1R,2S,5S)-2-methyl-3-oxo-5-(prop-1-en-2-yl)cyclohexanecarbonitrile

(1S,2S,5S)-2-methyl-3-oxo-5-(prop-1-en-2-yl)cyclohexanecarbonitrile

Refernces

• 1、 Hudlicky, Jason R.,Werner, Lukas,Semak, Vladislav,Simionescu, Razvan,Hudlicky, Tomas. "Dauben-Michno oxidative transposition of allylic cyanohydrins - Enantiomeric switch of (-)-carvone to (+)-carvone". experimental part. p. 535 - 543. Retrieved 2011/10/03.