(E)-3-hydroxy-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)pent-4-enenitrile

Base Information

• Chemical Name: (E)-3-hydroxy-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)pent-4-enenitrile
• CAS No.: 94326-16-6
• Molecular Formula: C₁₅H₂₃NO
• Molecular Weight: 233.354
• Mol file: 94326-16-6.mol

Synonyms:(E)-3-hydroxy-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)pent-4-enenitrile

Chemical Property of (E)-3-hydroxy-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)pent-4-enenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-hydroxy-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)pent-4-enenitrile

There total 5 articles about (E)-3-hydroxy-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)pent-4-enenitrile 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: 85.0%

(E)-β-ionone (79-77-6,14901-07-6) + acetonitrile (75-05-8,26809-02-9) → (E)-3-hydroxy-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)pent-4-enenitrile (94326-16-6)

Guidance literature:

acetonitrile; With n-butyllithium; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

(E)-β-ionone; In tetrahydrofuran; at -78 - 20 ℃; for 3.16667h; Inert atmosphere;

DOI:10.1016/j.ejmech.2013.09.057

Reference yield: 63.0%

(7E)-9-ethynyl-β-ionol (17974-59-3) → (E)-3-hydroxy-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)pent-4-enenitrile (94326-16-6) + C15H24N2

Guidance literature:

With C₂₄H₂₀N₂O₄Ru; hydrazine hydrate; In toluene; at 150 ℃; Inert atmosphere; Microwave irradiation;

DOI:10.24820/ark.5550190.p010.893

Reference yield:

4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one (79-77-6,14901-07-6) + cyanomethyl bromide (590-17-0) → 3-Hydroxy-3-methyl-1-(2.6.6-trimethyl-cyclohexen-(1)-yl)-penten-(1)-saeure-(5)-nitril, β-Ionolacetonitril (94326-16-6)

Guidance literature:

With zinc;

upstream raw materials:

4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one

cyanomethyl bromide

(E)-β-ionone

acetonitrile

Downstream raw materials:

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

(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoic acid

(2Z,4E)-3-methyl-5-(2’,6’,6’-trimethylcyclohex-1’-en-1’-yl)-penta-2,4-dienenitrile

Refernces

• 1、 Pori, Matteo,Galletti, Paola,Soldati, Roberto,Calzà, Laura,Mangano, Chiara,Giacomini, Daria. "Azetidinone-retinoid hybrids: Synthesis and differentiative effects". . p. 857 - 863. Retrieved 2013/12/04.