Pentanoic acid, 4-methyl-2-methylene-, phenylmethyl ester

Base Information

• Chemical Name: Pentanoic acid, 4-methyl-2-methylene-, phenylmethyl ester
• CAS No.: 118053-31-9
• Molecular Formula: C14H18O2
• Molecular Weight: 218.296
• DSSTox Substance ID: DTXSID50457969
• Nikkaji Number: J1.876.551I
• Mol file: 118053-31-9.mol

Synonyms:benzyl 2-isobutylacrylate;Pentanoic acid, 4-methyl-2-methylene-, phenylmethyl ester;118053-31-9;SCHEMBL6851044;DTXSID50457969;KRRNMUYRNUTOTQ-UHFFFAOYSA-N;2-Isobutylacrylic acid benzyl ester

Chemical Property of Pentanoic acid, 4-methyl-2-methylene-, phenylmethyl ester

Chemical Property:

• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 218.130679813
• Heavy Atom Count: 16
• Complexity: 237

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(=C)C(=O)OCC1=CC=CC=C1

Technology Process of Pentanoic acid, 4-methyl-2-methylene-, phenylmethyl ester

There total 4 articles about Pentanoic acid, 4-methyl-2-methylene-, phenylmethyl 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: 94.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2-acetyl-4-methyl-pentanoic acid benzyl ester (501330-86-5) → benzyl 4-methyl-2-methylenepentanoate (118053-31-9)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at 20 ℃; for 6h;

DOI:10.1021/jo026738b

Reference yield: 62.0%

2-iodo-propane (75-30-9) + benzyl 2-((phenylsulfonyl)methyl)acrylate → benzyl 4-methyl-2-methylenepentanoate (118053-31-9)

Guidance literature:

With dimanganese decacarbonyl; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; In dimethyl sulfoxide; at 20 ℃; for 24h; Inert atmosphere; Sealed tube; Irradiation;

DOI:10.1021/acs.joc.0c00861

Reference yield:

benzyl acetoacetate (5396-89-4) → benzyl 4-methyl-2-methylenepentanoate (118053-31-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / t-BuOK / tetrahydrofuran / 12 h / 70 °C

2: 94 percent / LiHMDS / tetrahydrofuran / 6 h / 20 °C

With potassium tert-butylate; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1021/jo026738b

upstream raw materials:

formaldehyd

2-acetyl-4-methyl-pentanoic acid benzyl ester

benzyl acetoacetate

2-isopropoxyisoindoline-1,3-dione

Downstream raw materials:

(R,R,S,S)-2-isobutyl-3-((1-(N-(9-fluorenylmethoxycarbonyl)amino)-2-phenylethyl)-hydroxyphosphinyl) propanoic acid, benzyl ester

(R,R,S,S)-2-isobutyl-3-((1-(N-(9-fluorenylmethoxycarbonyl)amino)-ethyl)-hydroxyphosphinyl) propanoic acid, benzyl ester

[(RS)-2-[(benzyloxy)carbonyl]-4-methylpentyl]phosphinic acid

(S)-2-[2-(Benzyl-methoxy-phosphinoylmethyl)-4-methyl-pentanoylamino]-propionic acid methyl ester