3-heptenoic acid, 6-methyl-

Base Information

• Chemical Name: 3-heptenoic acid, 6-methyl-
• CAS No.: 168213-35-2
• Molecular Formula: C₈H₁₄O₂
• Molecular Weight: 142.198
• Mol file: 168213-35-2.mol

Synonyms:

Chemical Property of 3-heptenoic acid, 6-methyl-

Chemical Property:

• Vapor Pressure: 0.016mmHg at 25°C

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-heptenoic acid, 6-methyl-

There total 12 articles about 3-heptenoic acid, 6-methyl- 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%

penta-3,4-dienoic acid (60053-24-9) + isopropylmagnesium bromide (920-39-8) → (E)-6-methylhept-3-enoic acid (1016225-27-6,168213-35-2)

Guidance literature:

penta-3,4-dienoic acid; isopropylmagnesium bromide; With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; at 0 ℃; for 3h; Reflux; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; water; Reagent/catalyst; Temperature; stereoselective reaction; Inert atmosphere;

DOI:10.1002/chem.201403294

Reference yield: 68.0%

malonic acid (141-82-2) + isovaleraldehyde (590-86-3) → C8H14O2 (168213-35-2)

Guidance literature:

With piperidine; acetic acid; In dimethyl sulfoxide; at 20 - 100 ℃;

DOI:10.1021/acs.orglett.7b01392

Reference yield: 63.0%

malonic acid (141-82-2) + isocaproic aldehyde (1119-16-0) → (E)-6-methylhept-3-enoic acid (1016225-27-6,168213-35-2)

Guidance literature:

With piperidine; acetic acid; In dimethyl sulfoxide; at 20 - 110 ℃; for 4.5h;

DOI:10.1021/ja710492q

upstream raw materials:

trans-1-Bromo-5-methylhex-2-ene

carbon dioxide

malonic acid

isocaproic aldehyde

Downstream raw materials:

(S)-3-hydroxy-6-methylheptanoic acid phenyl amide

(S)-6-methyl-3-(4,4,6-trimethyl-1,3,2-dioxaborato)heptanoic acid phenyl amide

Refernces

• 1、 Wang, Hao,Bai, Zibo,Jiao, Tangqian,Deng, Zhiqiang,Tong, Huarong,He, Gang,Peng, Qian,Chen, Gong. "Palladium-Catalyzed Amide-Directed Enantioselective Hydrocarbofunctionalization of Unactivated Alkenes Using a Chiral Monodentate Oxazoline Ligand". supporting information. p. 3542 - 3546. Retrieved 2018/03/21.
• 2、 Desrat, Sandy,Gray, Philip J.,Penny, Matthew R.,Motherwell, William B.. "Taming the carboxyl group for directed carbometalation: Observations on the use of anions, dianions and ester enolates". . p. 8918 - 8922. Retrieved 2014/07/22.