(S)-(-)-1(E)-(5,5-dimethyl-2-isopropenylcyclohexylidene)acetonitrile

Base Information

• Chemical Name: (S)-(-)-1(E)-(5,5-dimethyl-2-isopropenylcyclohexylidene)acetonitrile
• CAS No.: 142835-93-6
• Molecular Formula: C₁₃H₁₉N
• Molecular Weight: 189.301
• Mol file: 142835-93-6.mol

Synonyms:(S)-(-)-1(E)-(5,5-dimethyl-2-isopropenylcyclohexylidene)acetonitrile

Chemical Property of (S)-(-)-1(E)-(5,5-dimethyl-2-isopropenylcyclohexylidene)acetonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(-)-1(E)-(5,5-dimethyl-2-isopropenylcyclohexylidene)acetonitrile

There total 4 articles about (S)-(-)-1(E)-(5,5-dimethyl-2-isopropenylcyclohexylidene)acetonitrile 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: 98.0%

(1R,2R,αR,Rs)-(+)-5,5-dimethyl-2-isopropenyl-α-p-toluenesulfinylcyclohexaneacetonitrile (142835-85-6) → (S)-(-)-1(E)-(5,5-dimethyl-2-isopropenylcyclohexylidene)acetonitrile (142835-93-6)

Guidance literature:

In tetrachloromethane; for 4h; Heating;

DOI:10.1016/S0040-4020(01)80539-1

Reference yield:

3,3,7-trimethyl-oct-6-enal (17920-90-0) → (S)-(-)-1(E)-(5,5-dimethyl-2-isopropenylcyclohexylidene)acetonitrile (142835-93-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / piperidinium acetate, molecular sieves 4A / benzene / 24 h / Ambient temperature

2: CH₂Cl₂ / 2 h / -20 °C / diastereoselectivity, Et₂AlCl catalyzed intramolecular ene reaction, other Lewis acids, solvents, temperatures

3: 98 percent / CCl₄ / 4 h / Heating

With 4 A molecular sieve; piperdinium acetate; In tetrachloromethane; dichloromethane; benzene;

DOI:10.1016/S0040-4020(01)80539-1

Reference yield:

(R)-(+)-cyanomethyl p-tolyl sulfoxide (63923-58-0) → (S)-(-)-1(E)-(5,5-dimethyl-2-isopropenylcyclohexylidene)acetonitrile (142835-93-6)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₂AlCl / CH₂Cl₂ / 2 h / -20 °C

2: CCl₄ / Heating

diethylaluminium chloride; In tetrachloromethane; dichloromethane;

DOI:10.1016/S0040-4039(00)92084-7

upstream raw materials:

(1R,2R,αR,Rs)-(+)-5,5-dimethyl-2-isopropenyl-α-p-toluenesulfinylcyclohexaneacetonitrile

3,3,7-trimethyl-oct-6-enal

(S)-(+)-5,5,9-trimethyl-2-p-toluenesulfinyl-2,8-decadienonitrile

(R)-(+)-cyanomethyl p-tolyl sulfoxide

Downstream raw materials:

(S)-(-)-1-(E)-(5,5-dimethyl-2-isopropenylcyclohexylidene)-2-propanone

(S)-(-)-1(E)-(5,5-dimethyl-2-isopropenylcyclohexylidene)acetaldehyde