3,4-Dehydrobrevicomin

Base Information

• Chemical Name: 3,4-Dehydrobrevicomin
• CAS No.: 62255-25-8
• Molecular Formula: C9H14O2
• Molecular Weight: 154.2063
• Mol file: 62255-25-8.mol

Synonyms:(+/-)-exo-Mus musculus pheromone;exo-3,4-dehydrobrevicomin;(+/-)-3,4-dehydro-exo-brevicomin;7-exo-Ethyl-5-methyl-6,8-dioxabicyclo<3.2.1>oct-3-ene;3,4-Dehydrobrevicomin;exo-7-ethyl-5-methyl-6,8-dioxabicyclo

Chemical Property of 3,4-Dehydrobrevicomin

Chemical Property:

• Vapor Pressure: 0.711mmHg at 25°C
• Boiling Point: 191.6°Cat760mmHg
• Flash Point: 64.4°C
• PSA: 18.46000
• Density: 1.023g/cm³
• LogP: 1.85650

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3,4-Dehydrobrevicomin

There total 63 articles about 3,4-Dehydrobrevicomin 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: 100.0%

(Z)-5-((2S,3S)-3-Ethyl-oxiranyl)-pent-3-en-2-one (109322-33-0,109429-38-1,110043-72-6,110043-73-7) → (+/-)-endo-Mus musculus pheromone (62255-25-8,88525-42-2,93426-67-6,109429-32-5,109429-39-2,110043-74-8,159912-77-3)

Guidance literature:

With zinc(II) chloride;

DOI:10.1016/S0040-4039(00)85095-9

Reference yield: 48.0%

exo-7-ethyl-5-methyl-4-phenylseleno-6,8-dioxabicyclo<3.2.1>octane (93426-68-7,97989-76-9,110659-34-2,110659-35-3,110659-36-4,110659-37-5) → exo-7-ethyl-5-methyl-6,8-dioxabicyclo<3.2.1>oct-3-ene (62255-25-8,88525-42-2,93426-67-6,109429-32-5,109429-39-2,110043-74-8,159912-77-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/S0040-4020(01)96072-7

Reference yield: 45.0%

5-((2S,3R)-3-Ethyl-oxiranyl)-pent-3-yn-2-one (109322-32-9) → (2R,5S,7R)-exo-7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]oct-3-ene (62255-25-8,88525-42-2,93426-67-6,109429-32-5,109429-39-2,110043-74-8,159912-77-3) + (Z)-5-((2S,3R)-3-Ethyl-oxiranyl)-pent-3-en-2-one (109322-33-0)

Guidance literature:

With hydrogen; Lindlar's catalyst;

DOI:10.1016/S0040-4039(00)85096-0

upstream raw materials:

(Z)-5-((2S,3R)-3-Ethyl-oxiranyl)-pent-3-en-2-one

5-((2S,3R)-3-Ethyl-oxiranyl)-pent-3-yn-2-one

(2R,4RS,6S,7R)-exo-7-ethyl-5-methyl-4-phenylseleno-6,8-dioxabicyclo[3.2.1]octane

(1S,5S,7R)-7-ethyl-5-methyl-1-p-tolylsulfanyl-6,8-dioxabicyclo<3.2.1>octane

Refernces

• 1、 Mori, Kenji. "Protective group-free syntheses of (±)-frontalin, (±)-endo-brevicomin, (±)-exo-brevicomin, and (±)-3,4- dehydro-exo-brevicomin: Racemic pheromones with a 6,8-dioxabicyclo[3.2.1]octane ring". experimental part. p. 976 - 981. Retrieved 2012/01/05.
• 2、 Tashiro, Takuya,Mori, Kenji. "Pheromone synthesis, CXCVII. Synthesis of the enantiomers of 2-sec- butyl-4,5-dihydrothiazole and (1R,5S,7R)-3,4-dehydro-exo-brevicomin, pheromone components of the male mouse, Mus musculus". . p. 2167 - 2173. Retrieved 2007/10/03.