3-Benzyl-4-methoxy-4-oxobutanoate

Base Information

• Chemical Name: 3-Benzyl-4-methoxy-4-oxobutanoate
• CAS No.: 182247-45-6
• Molecular Formula: C12H14O4
• Molecular Weight: 222.241
• Hs Code.: 29171990
• DSSTox Substance ID: DTXSID50939553
• Wikidata: Q82916050
• Mol file: 182247-45-6.mol

Synonyms:DTXSID50939553;3-Benzyl-4-methoxy-4-oxobutanoate;(S)-(-)-3-Methoxycarbonyl-4-phenylbutyric acid

Chemical Property of 3-Benzyl-4-methoxy-4-oxobutanoate

Chemical Property:

• Appearance/Colour: yellow viscous liquid
• Vapor Pressure: 5.84E-06mmHg at 25°C
• Refractive Index: 1.529
• Boiling Point: 364.7 °C at 760 mmHg
• Flash Point: 138.8 °C
• PSA: 63.60000
• Density: 1.189 g/cm³
• LogP: 1.49300
• Storage Temp.: Refrigerator (+4°C)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 221.08138389
• Heavy Atom Count: 16
• Complexity: 238

Purity/Quality:

97% ^*data from raw suppliers

(S)-3-Benzyl-4-methoxy-4-oxobutanoicacid 95+% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CC1=CC=CC=C1)CC(=O)[O-]
• Isomeric SMILES: COC(=O)[C@@H](CC1=CC=CC=C1)CC(=O)[O-]

Technology Process of 3-Benzyl-4-methoxy-4-oxobutanoate

There total 3 articles about 3-Benzyl-4-methoxy-4-oxobutanoate 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:

3-(methoxycarbonyl)-4phenylbut-3-enoic acid → (S)-3-benzyl-4-methoxy-4-oxobutanoic acid (182247-45-6) + (R)-3-benzyl-4-methoxy-4-oxobutanoic acid (119807-84-0)

Guidance literature:

With hydrogen; [Rh(S,S,R,R)TangPhos(nbd)]SbF₆; In tetrahydrofuran; at 20 ℃; for 24h; under 1034.32 Torr; Title compound not separated from byproducts.;

DOI:10.1021/ol0272592

Reference yield:

3-(methoxycarbonyl)-4phenylbut-3-enoic acid → (S)-3-benzyl-4-methoxy-4-oxobutanoic acid (182247-45-6)

Guidance literature:

With hydrogen; 2,3-bis-[(R,R)-2,5-dimethylphospholan-1-yl]-maleic anhydride; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; In dichloromethane; at 25 ℃; for 5h; under 3000.3 Torr;

DOI:10.1002/adsc.200404080

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + dimethyl 2-benzylsuccinate (35262-43-2) → (S)-3-benzyl-4-methoxy-4-oxobutanoic acid (182247-45-6)

Guidance literature:

With porcine pancrease lipase; Yield given. Multistep reaction; 1) 0.1M KHPO₄ buffer (pH = 7.2), 3) 0.1M KHPO₄ buffer (pH = 7.2);

DOI:10.1016/0040-4039(96)01339-1

upstream raw materials:

diazomethane

dimethyl 2-benzylsuccinate

Downstream raw materials:

(S)-2-Benzyl-succinic acid bis-(2-trimethylsilanyl-ethyl) ester

(2S)-benzylsuccinic acid