NONACOSADIENE (7Z,11Z)

Base Information

• Chemical Name: NONACOSADIENE (7Z,11Z)
• CAS No.: 104410-91-5
• Molecular Formula: C29H56
• Molecular Weight: 404.75500
• Mol file: 104410-91-5.mol

Synonyms:

Chemical Property of NONACOSADIENE (7Z,11Z)

Chemical Property:

• PSA: 0.00000
• LogP: 11.11090

Purity/Quality:

98.5% ^*data from raw suppliers

7(Z),11(Z)-Nonacosadiene ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Unsaturated cuticular hydrocarbons serve as pheromones in insects. In D. melanogaster, these hydrocarbons are sexually dimorphic in both their occurrence and their effects. 7(Z),11(Z)-Nonacosadiene is a cuticular pheromone in female fruit flies that stimulates male courtship behavior. The biosynthesis of this C29 diene appears to be mediated by an elongase with female-based expression.

Technology Process of NONACOSADIENE (7Z,11Z)

There total 32 articles about NONACOSADIENE (7Z,11Z) 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: 95.0%

Methanesulfonic acid (7Z,11Z)-1-undecyl-octadeca-7,11-dienyl ester (125043-72-3) → 7(Z),11(Z)-nonacosadiene (104410-91-5)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; 1) 0 deg C, 0.5 h; 2) 30 deg C, 1 h;

Reference yield:

C30H58O3S → 7(Z),11(Z)-nonacosadiene (104410-91-5)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 - 30 ℃; for 1.5h; Inert atmosphere;

DOI:10.1016/j.tetlet.2017.03.061

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → 7(Z),11(Z)-nonacosadiene (104410-91-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Mg, 2.) methyl Grignard reagent / 2.) bis(diphenylphosphino)propanenickel(II) chloride / 1.) Et₂O, 2.) C₆H₆, reflux, overnight

2: 54 percent / PCC / CH₂Cl₂ / 4 h / 25 °C

3: HMPT / hexane; tetrahydrofuran / -65 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; methyl Grignard reagent; magnesium; pyridinium chlorochromate; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1055/s-1989-27435

upstream raw materials:

(Z)-undec-4-en-1-ol

Phosphonium salt of [1-BROMOOCTADECANE]

(Z)-4-undecenal

Octadecyltriphenylphosphorane