3,3-Dimethyl-4-pentenoic acid

Base Information

• Chemical Name: 3,3-Dimethyl-4-pentenoic acid
• CAS No.: 7796-73-8
• Molecular Formula: C7H12O2
• Molecular Weight: 128.171
• DSSTox Substance ID: DTXSID70442630
• Nikkaji Number: J1.090.121I
• Wikidata: Q82260012
• Mol file: 7796-73-8.mol

Synonyms:3,3-DIMETHYL-4-PENTENOIC ACID;7796-73-8;3,3-dimethylpent-4-enoic Acid;4-Pentenoic acid, 3,3-dimethyl-;3,3-Dimethylpentensaure;3,3-dimethypent-4-enoic acid;SCHEMBL1821089;4-Pentenoicacid,3,3-dimethyl-;DTXSID70442630;FYYOTZLMLLTWAP-UHFFFAOYSA-N;MFCD03425851;AKOS000278319;BS-36187;CS-0222065;EN300-110223;Z1198162637

Chemical Property of 3,3-Dimethyl-4-pentenoic acid

Chemical Property:

• PSA: 37.30000
• LogP: 1.67330
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 128.083729621
• Heavy Atom Count: 9
• Complexity: 125

Purity/Quality:

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

3,3-dimethyl-4-pentenoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(CC(=O)O)C=C

Technology Process of 3,3-Dimethyl-4-pentenoic acid

There total 12 articles about 3,3-Dimethyl-4-pentenoic acid 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%

methyl 3,3-dimethyl-4-penteneoate (63721-05-1) → 3,3-dimethylpent-4-enoic acid (7796-73-8)

Guidance literature:

methyl 3,3-dimethyl-4-penteneoate; With sodium hydroxide; In water; Reflux;

With hydrogenchloride; In water; at 20 ℃;

DOI:10.1021/jacs.8b02124

Reference yield: 95.0%

Triethyl orthoacetate (78-39-7) + 3-methyl-2-buten-1-ol (556-82-1) → 3,3-dimethylpent-4-enoic acid (7796-73-8)

Guidance literature:

Triethyl orthoacetate; 3-methyl-2-buten-1-ol; With phenol; at 160 ℃; for 16h; Dean-Stark;

With sodium hydroxide; In methanol; water; at 100 ℃; for 1h; Dean-Stark;

DOI:10.1021/acs.orglett.8b00996

Reference yield: 74.0%

ethyl 3,3-dimethylpent-4-enoate (7796-72-7) → 3,3-dimethylpent-4-enoic acid (7796-73-8)

Guidance literature:

With sodium hydroxide; for 4h; Ambient temperature;

DOI:10.1021/jo00376a076

upstream raw materials:

1-diazo-5-methyl-hex-4-en-2-one

ethyl 3,3-dimethylpent-4-enoate

Triethyl orthoacetate

3-methyl-2-buten-1-ol

Downstream raw materials:

3,3-Dimethyl-4-penten-4-olide

Refernces

• 1、 Mori, Kenji. "Pheromone synthesis. Part 264: Synthesis of the core 3-oxabicyclo[3.3.0]octane structures of gomadalactones A, B and C, the components of the contact sex pheromone of the white-spotted longicorn beetle, Anoplophora malasiaca". . p. 3387 - 3398. Retrieved 2019/05/15.
• 2、 McCourt, Ruairi O.,Dénès, Fabrice,Sanchez-Sanz, Goar,Scanlan, Eoin M.. "Rapid Access to Thiolactone Derivatives through Radical-Mediated Acyl Thiol-Ene and Acyl Thiol-Yne Cyclization". supporting information. p. 2948 - 2951. Retrieved 2018/05/28.