2,6-Dimethyloct-7-en-4-one

Base Information

• Chemical Name: 2,6-Dimethyloct-7-en-4-one
• CAS No.: 1879-00-1
• Deprecated CAS: 24739-77-3,70286-41-8
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.252
• European Community (EC) Number: 217-532-6
• DSSTox Substance ID: DTXSID70883766
• Nikkaji Number: J199.698C,J85.986I
• Wikidata: Q67879926
• Mol file: 1879-00-1.mol

Synonyms:Dihydro Tagetone;2,6-Dimethyloct-7-en-4-one;Dihydrotagetone;1879-00-1;7-Octen-4-one, 2,6-dimethyl-;EINECS 217-532-6;2,6-Dimethyl-7-octen-4-one;SCHEMBL6903513;DTXSID70883766;(+)-2,6-Dimethyl-7-octen-4-one;AKOS017341560;FT-0667137;J-012098;Q67879926

Chemical Property of 2,6-Dimethyloct-7-en-4-one

Chemical Property:

• Vapor Pressure: 0.289mmHg at 25°C
• Boiling Point: 202.6°Cat760mmHg
• Flash Point: 65.8°C
• PSA: 17.07000
• Density: 0.826g/cm³
• LogP: 2.81380
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 136

Purity/Quality:

98%,99%, ^*data from raw suppliers

DihydroTagetone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(=O)CC(C)C=C
• Uses: A metabolite of Tagetone, an antimicrobial agent against fungi, bacteria and protozoa.

Technology Process of 2,6-Dimethyloct-7-en-4-one

There total 13 articles about 2,6-Dimethyloct-7-en-4-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: 64.0%

3-bromo-1-butene (22037-73-6) + 4-methyl-2-trimethylsilyloxy-1-pentene (59417-87-7) → 2,6-dimethyl-7-octene-4-one (1879-00-1,1005194-62-6)

Guidance literature:

With aluminum oxide; zinc(II) chloride; at -10 ℃; for 1.5h;

DOI:10.1080/00397919908085973

Reference yield: 30.0%

buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) + 4-methyl-2-pentanone (108-10-1) → 2,6-dimethyl-7-octene-4-one (1879-00-1,1005194-62-6)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; In water; at 130 ℃; for 2h; Glovebox; Sealed tube;

Reference yield:

isovaleraldehyde (590-86-3) + isoprene (78-79-5,9003-31-0) → 2,6-dimethyl-7-octene-4-one (1879-00-1,1005194-62-6)

Guidance literature:

With (dcype)CoBr₂; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; zinc; In dichloromethane; at 20 ℃; regioselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.1c06245

upstream raw materials:

(E/Z)-2-buten-1-ol

5-methyl-3-oxo-hexanoic acid ethyl ester

Isobutyl bromide

3-methylpent-4-enoic acid chloride

Downstream raw materials:

3-methylbutyric acid

4-methyl-2-pentanone

butanone

formic acid

Refernces

• 1、 -. "gamma-alkenyl ketone and preparation method thereof". Paragraph 0031; 0156-0159. . Retrieved 2020/02/29.
• 2、 Kad,Singh, Vasundhara,Khurana, Anupam,Chaudhary, Sangeeta,Singh, Jasvinder. "Regioselective α-alkylation of silyl enolates using a mild catalyst- ZnCl2 doped on acidic alumina". . p. 3439 - 3442. Retrieved 2007/10/03.