(2Z,4E)-3-METHYL-5-(2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)-PENTA-2,4-DIENENITRILE

Base Information

• Chemical Name: (2Z,4E)-3-METHYL-5-(2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)-PENTA-2,4-DIENENITRILE
• CAS No.: 1155402-76-8
• Molecular Formula: C₁₅H₂₁N
• Molecular Weight: 215.338
• Mol file: 1155402-76-8.mol

Synonyms:(2Z,4E)-3-METHYL-5-(2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)-PENTA-2,4-DIENENITRILE;(+/-)-(7E,9Z)-(α-Ionylidene)acetonitrile

Chemical Property of (2Z,4E)-3-METHYL-5-(2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)-PENTA-2,4-DIENENITRILE

Chemical Property:

• Boiling Point: 78-84°C @ 0.1mm
• PSA: 23.79000
• LogP: 4.53908
• Solubility.: Dichloromethane, Ether, Ethyl Acetate, Hexane

Purity/Quality:

98%Min ^*data from raw suppliers

(2Z,4E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)penta-2,4-dienenitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An intermediate of (3R,3'R,6'R)-Lutein and (3R,3'R)-Zeaxanthin, two dietary carotenoids that are present in most fruits and vegetables An intermediate of (3R,3''R,6''R)-Lutein and (3R,3''R)-Zeaxanthin, two dietary carotenoids that are present in most fruits and vegetables.

Technology Process of (2Z,4E)-3-METHYL-5-(2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)-PENTA-2,4-DIENENITRILE

There total 12 articles about (2Z,4E)-3-METHYL-5-(2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)-PENTA-2,4-DIENENITRILE 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:

diisopropyl (cyanomethyl)phosphonate (21658-95-7) + alpha-ionone (127-41-3,6901-97-9,14398-36-8,24190-29-2,30685-95-1,31798-12-6,52340-45-1,67529-94-6,67529-95-7) → (2E,4E)-3-methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)penta-2,4-dienenitrile (58260-81-4,1155402-76-8) + (2Z,4E)-3-methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)penta-2,4-dienenitrile (1155402-76-8)

Guidance literature:

diisopropyl (cyanomethyl)phosphonate; With sodium methylate; In tert-butyl methyl ether; at 0 - 20 ℃; Inert atmosphere;

alpha-ionone; In tert-butyl methyl ether; at 0 - 20 ℃; optical yield given as %de; Inert atmosphere;

DOI:10.1021/jo900432r

Reference yield:

diisopropyl (cyanomethyl)phosphonate (21658-95-7) + alpha-ionone (127-41-3,6901-97-9,14398-36-8,24190-29-2,30685-95-1,31798-12-6,52340-45-1,67529-94-6,67529-95-7) → (2E,4E)-3-methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)penta-2,4-dienenitrile (58260-81-4,1155402-76-8) + (2Z,4E)-3-methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)penta-2,4-dienenitrile (1155402-76-8)

Guidance literature:

diisopropyl (cyanomethyl)phosphonate; With sodium methylate; In tert-butyl methyl ether; at 0 - 20 ℃; Inert atmosphere;

alpha-ionone; In tert-butyl methyl ether; at 0 - 20 ℃; optical yield given as %de; Inert atmosphere;

DOI:10.1021/jo900432r

Reference yield:

alpha-ionone (127-41-3,6901-97-9,14398-36-8,24190-29-2,30685-95-1,31798-12-6,52340-45-1,67529-94-6,67529-95-7) + cyanoacetic acid (372-09-8) → (2E,4E)-3-methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)penta-2,4-dienenitrile (58260-81-4,1155402-76-8) + (2Z,4E)-3-methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)penta-2,4-dienenitrile (1155402-76-8)

Guidance literature:

With cyclohexylamine; at 80 - 85 ℃; for 3.5h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/jo900432r

upstream raw materials:

alpha-ionone

diethyl (3-cyano-2-methyl-2-trans-propenyl)phosphonate

α-cyclocitral

diisopropyl (cyanomethyl)phosphonate

Refernces

• 1、 -. "Process for Synthesis of (3R,3'R,6'R)-Lutein and its Stereoisomers". Page/Page column 6-7; 19. . Retrieved 2009/10/30.