Peachflure

Base Information

• Chemical Name: Peachflure
• CAS No.: 63408-44-6
• Molecular Formula: C20H38O
• Molecular Weight: 294.521
• Mol file: 63408-44-6.mol

Synonyms:(Z)-13-Icosen-10-one;(Z)-7-Icosen-11-one;Peachflure;(Z)-7-Eicosen-11-one;7Z-20-11Kt;(Z)-13-Eicosen-10-one;Z-7-Eicosene-11-one

Chemical Property of Peachflure

Chemical Property:

• Boiling Point: 172 °C(Press: 1 Torr)
• PSA: 17.07000
• Density: 0.842±0.06 g/cm3(Predicted)
• LogP: 7.00300

Purity/Quality:

> 90% ^*data from raw suppliers

(13Z)-Eicosen-10-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (13Z)-Eicosen-10-one can be utilized in biological study and agricultural use in method of producing sustained release lure for pest control, by mixing perimones inducible for e.g. aphids and ticks, with organic solvent, supporting pheromone solution to an inorganic carrier and introducing the complex to sunscreen container.

Technology Process of Peachflure

There total 7 articles about Peachflure 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: 61.0%

triphenylheptylphosphonium bromide (13423-48-8) + 4-oxo-tridecan-1-al (77328-83-7) → (13Z)-eicos-13-en-10-one (63408-44-6) + Triphenylphosphine oxide (791-28-6)

Guidance literature:

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

Reference yield:

1,4-tridecanediol (61828-34-0) + triphenylheptylphosphonium bromide (13423-48-8) → (13Z)-eicos-13-en-10-one (63408-44-6) + Triphenylphosphine oxide (791-28-6)

Guidance literature:

With hexamethyldisilazide; 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, 25 deg C 12 h;

Reference yield:

triphenylheptylphosphonium bromide (13423-48-8) + 4-oxo-tridecan-1-al (77328-83-7) → (13Z)-eicos-13-en-10-one (63408-44-6) + (E)-7-Eicosan-11-one (63408-50-4)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; dichloromethane; at 0 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

upstream raw materials:

1,4-tridecanediol

triphenylheptylphosphonium bromide

4-oxo-tridecan-1-al

n-nonyllithium

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.