(Z)-7-Nonadecen-11-one

Base Information

• Chemical Name: (Z)-7-Nonadecen-11-one
• CAS No.: 63408-45-7
• Molecular Formula: C19H36O
• Molecular Weight: 280.494
• Hs Code.: 2914190090
• Mol file: 63408-45-7.mol

Synonyms:12-Nonadecen-9-one,(Z);12-Nonadecen-9-one,(E);

Chemical Property of (Z)-7-Nonadecen-11-one

Chemical Property:

• Boiling Point: 167 °C(Press: 1 Torr)
• PSA: 17.07000
• Density: 0.842±0.06 g/cm3(Predicted)
• LogP: 6.61290

Purity/Quality:

99% ^*data from raw suppliers

(12Z)-Nonadecen-9-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (12Z)-Nonadecen-9-one can be used in biological study of (Z)-7-Tricosene and monounsaturated ketones as sex pheromone components of the Australian guava moth Coscinoptycha improbana: Identification, field trapping, and phenology.

Technology Process of (Z)-7-Nonadecen-11-one

There total 13 articles about (Z)-7-Nonadecen-11-one 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: 89.0%

(Z)-7-nonadecen-11-ol (72855-91-5) → (Z)-12-nonadecen-9-one (63408-45-7) + (E)-7-nonadecen-11-one (63408-51-5)

Guidance literature:

With Dess-Martin periodane; In dichloromethane;

DOI:10.1021/acs.jafc.0c04131

Reference yield: 60.9%

4-oxo-dodecanal (56268-03-2) + triphenylheptylphosphonium bromide (13423-48-8) → (Z)-12-nonadecen-9-one (63408-45-7) + Triphenylphosphine oxide (791-28-6)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; -78 deg C, 1 h then 25 deg C 12 h;

Reference yield:

dodecane-1,4-diol (38146-95-1) + triphenylheptylphosphonium bromide (13423-48-8) → (Z)-12-nonadecen-9-one (63408-45-7) + Triphenylphosphine oxide (791-28-6)

Guidance literature:

With sodium hexamethyldisilazane; pyridinium chlorochromate; Yield given. Multistep reaction; 1) methylene chloride 20-25 deg C 2) THF 20 deg C 30 min, reflux 1 h 3) -78 deg C 1 h, 25 deg C 12 h;

upstream raw materials:

dodecane-1,4-diol

triphenylheptylphosphonium bromide

4-oxo-dodecanal

bromure d'heptyltriphenylphosphonium

Refernces

A New Synthesis of (Z)-13-Eicosen-10-one and (Z)-12-Nonadecen-9-one, the Pheromones of Peach Fruit Moth

10.1246/bcsj.55.3047

The research describes a new and simple synthesis method for (Z)-13-eicosen-10-one and (Z)-12-nonadecen-9-one, which are pheromones of the Japanese peach fruit moth. The synthesis process starts with 1-(p-tolylsulfonyl)nonane and 1-(p-tolylsulfonyl)octane. These compounds are condensed with methyl 4,4-dimethoxybutanoate using lithium diisopropylamide (LDA) to form sulfones. The sulfones are then treated with aluminum amalgam in aqueous tetrahydrofuran (THF) to yield dimethoxy ketones. These ketones are subsequently acidified with hydrochloric acid to form oxo aldehydes. Finally, a salt-free Wittig reaction using heptyltriphenylphosphonium bromide and sodium amide is employed to produce the desired pheromones. The method is advantageous due to its simplicity, short process, and relatively good yield compared to other reported methods.