6-Phenyl-5-hexenoic acid, methyl ester

Base Information

• Chemical Name: 6-Phenyl-5-hexenoic acid, methyl ester
• CAS No.: 85396-64-1
• Molecular Formula: C13H16O2
• Molecular Weight: 204.269
• DSSTox Substance ID: DTXSID101301674
• Nikkaji Number: J2.070.570A,J2.638.004I
• Mol file: 85396-64-1.mol

Synonyms:6-Phenyl-5-hexenoic acid, methyl ester;(E)-6-Phenyl-5-hexenoic acid methyl ester;85396-64-1;methyl 4-(p-styryl)-butanoate;CUAFVHKUQUVEAG-UXBLZVDNSA-N;DTXSID101301674;Methyl (5E)-6-phenyl-5-hexenoate;6-Phenyl-5-hexenoic acid methyl ester;Methyl (5E)-6-phenyl-5-hexenoate #

Chemical Property of 6-Phenyl-5-hexenoic acid, methyl ester

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 204.115029749
• Heavy Atom Count: 15
• Complexity: 203

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)CCCC=CC1=CC=CC=C1
• Isomeric SMILES: COC(=O)CCC/C=C/C1=CC=CC=C1

Technology Process of 6-Phenyl-5-hexenoic acid, methyl ester

There total 12 articles about 6-Phenyl-5-hexenoic acid, methyl ester 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: 88.0%

methyl 5-hexenoate (2396-80-7) + C6H5N2(1+)*BF4 → (E)-6-phenyl-5-hexenoic acid methyl ester (85396-64-1)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In N,N-dimethyl acetamide; at 20 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1021/ja5056774

Reference yield:

methyl 6-phenylhex-5-ynoate (131070-58-1) → (Z)-6-phenyl-5-hexenoic acid methyl ester (85387-68-4) + (E)-6-phenyl-5-hexenoic acid methyl ester (85396-64-1)

Guidance literature:

With diphenylsilane; water; C₃₂H₄₈Cl₂Co₂N₆O₂; sodium triethylborohydride; In tetrahydrofuran; at 30 ℃; for 12h; Overall yield = 78percent; stereoselective reaction;

DOI:10.1021/acscatal.1c04141

Reference yield:

methyl 5-hexenoate (2396-80-7) + phenylboronic acid (98-80-6) → (E)-methyl 5-phenylhex-5-enoate (102312-78-7) + (E)-6-phenyl-5-hexenoic acid methyl ester (85396-64-1) + methyl trans-6-phenyl-4-hexenoate (189080-22-6)

Guidance literature:

With 1,2-bis(phenylsulfinyl)ethane palladium(II) acetate; acetic acid; p-benzoquinone; In 1,4-dioxane; at 20 ℃; for 24h;

DOI:10.1021/ja804120r

upstream raw materials:

diazomethane

(E/Z)-6-Phenylhex-5-enoic acid

methyl 5-iodopentanoate

benzaldehyde

Downstream raw materials:

6-phenylhex-5-en-1-ol

phenyl-6 hexene-5 ol-1 (E)

trans-6-phenyl-5-hexenal

(E)-7-phenylhept-6-en-2-one