(2E,4E,6E)-3-Methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trienenitrile

Base Information

• Chemical Name: (2E,4E,6E)-3-Methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trienenitrile
• CAS No.: 135322-84-8
• Molecular Formula: C₁₇H₂₃N
• Molecular Weight: 241.376
• Mol file: 135322-84-8.mol

Synonyms:

Chemical Property of (2E,4E,6E)-3-Methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trienenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4E,6E)-3-Methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trienenitrile

There total 7 articles about (2E,4E,6E)-3-Methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trienenitrile 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:

diethyl 1-cyanomethylphosphonate (2537-48-6) + (E,E)-6-(2,6,6-trimethylcyclohex-1-enyl)hexa-3,5-dien-2-one (99647-05-9) → (2E,4E,6E)-3-Methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trienenitrile (135322-84-8)

Guidance literature:

With sodium hydride; In 1,2-dimethoxyethane; at 0 ℃;

DOI:10.1246/cl.1999.1051

Reference yield:

(E)-β-ionone (79-77-6,14901-07-6) → (2E,4E,6E)-3-Methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trienenitrile (135322-84-8)

Guidance literature:

Multi-step reaction with 5 steps

1: NaClO / methanol

2: LiAlH₄ / diethyl ether / 0 °C

3: MnO₂ / diethyl ether

4: NaOH / H₂O

5: NaH / 1,2-dimethoxy-ethane / 0 °C

With manganese(IV) oxide; sodium hydroxide; sodium hypochlorite; lithium aluminium tetrahydride; sodium hydride; In methanol; 1,2-dimethoxyethane; diethyl ether; water; 1: Oxidation / 2: Reduction / 3: Oxidation / 4: Condensation / 5: Wittig reaction;

DOI:10.1246/cl.1999.1051

Reference yield:

(E)-3-(2,6,6-Trimethyl-cyclohex-1-enyl)-propenal (53018-97-6,4951-40-0) → (2E,4E,6E)-3-Methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trienenitrile (135322-84-8)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOH / H₂O

2: NaH / 1,2-dimethoxy-ethane / 0 °C

With sodium hydroxide; sodium hydride; In 1,2-dimethoxyethane; water; 1: Condensation / 2: Wittig reaction;

DOI:10.1246/cl.1999.1051

upstream raw materials:

(E)-3-(2,6,6-Trimethyl-cyclohex-1-enyl)-propenal

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

diethyl 1-cyanomethylphosphonate

(E,E)-6-(2,6,6-trimethylcyclohex-1-enyl)hexa-3,5-dien-2-one

Downstream raw materials:

(2E,4E,6E)-3-Methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trienal

(2E,4E,6E,8E)-3,5-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenenitrile

(3E,5E,7E)-4-Methyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-3,5,7-trien-2-one

all-trans-11-methyl-9-demethylretinal

Refernces

• 1、 Colmenares, Leticia U.,Liu, Robert S. H.. "11-Methyl-9-demethylretinal and 11-Methyl-9,13-didemethylretinal. Effect of Altered Methyl Substitution Pattern on Polyene Conformation, Photoisomerization and Formation of Visual Pigment Analogs". . p. 3711 - 3718. Retrieved 2007/10/02.