3-(5-Oxotetrahydrofuran-2-yl)propanoic acid

Base Information

• Chemical Name: 3-(5-Oxotetrahydrofuran-2-yl)propanoic acid
• CAS No.: 6283-72-3
• Molecular Formula: C7H10O4
• Molecular Weight: 158.154
• NSC Number: 7709
• DSSTox Substance ID: DTXSID901016277
• Nikkaji Number: J1.043.199I
• Mol file: 6283-72-3.mol

Synonyms:6283-72-3;3-(5-oxotetrahydrofuran-2-yl)propanoic acid;3-(5-oxo-tetrahydro-furan-2-yl)-propionic acid;3-(5-oxooxolan-2-yl)propanoic acid;(S)-3-(5-Oxo-tetrahydro-furan-2-yl)-propionic acid;NSC7709;2-Furanpropanoic acid, tetrahydro-5-oxo-;SCHEMBL1114400;DTXSID901016277;NSC 7709;NSC-7709;MFCD20638236;3-(5-Oxo-2-oxolanyl)propionic acid;AKOS015908291;SB38007;SB40358;SB40359;3-(Perhydro-5-oxo-2-furyl)propionic acid;3-(5-oxotetrahydrofuran-2-yl)propanoicacid;CS-0342519;3-(5-Oxotetrahydro-2-furanyl)propanoic acid #;2,3,4,5-tetrahydro-5-oxo-2-furanpropanoic acid

Chemical Property of 3-(5-Oxotetrahydrofuran-2-yl)propanoic acid

Chemical Property:

• Vapor Pressure: 2.27E-07mmHg at 25°C
• Boiling Point: 395.8°Cat760mmHg
• Flash Point: 170.7°C
• Density: 1.265g/cm³
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 158.05790880
• Heavy Atom Count: 11
• Complexity: 175

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)OC1CCC(=O)O

Technology Process of 3-(5-Oxotetrahydrofuran-2-yl)propanoic acid

There total 19 articles about 3-(5-Oxotetrahydrofuran-2-yl)propanoic 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: 96.0%

4-Ketopimelic acid (502-50-1) → 3-(5-oxotetrahydro-2-furanyl)propanoic acid (6283-72-3)

Guidance literature:

With sodium hydroxide; sodium tetrahydroborate; for 12h;

DOI:10.1039/b301329b

Reference yield:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → 3-(5-oxotetrahydro-2-furanyl)propanoic acid (6283-72-3)

Guidance literature:

Multi-step reaction with 4 steps

1: PBr₃ / CH₂Cl₂ / -20 °C

2: 3.5 g / sodium / ethanol / 2 h / Heating

3: 1.8 g / H₂O, NaCl / dimethylsulfoxide / 6 h / 145 - 180 °C

4: methanesulfonic acid, formic acid / 6 h / Heating

With formic acid; methanesulfonic acid; water; sodium; phosphorus tribromide; sodium chloride; In ethanol; dichloromethane; dimethyl sulfoxide;

Reference yield:

4-oxopimelate (6317-49-3) → 3-(5-oxotetrahydro-2-furanyl)propanoic acid (6283-72-3)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / ethanol

2: acidic hydrolysis

With sodium tetrahydroborate; In ethanol;

DOI:10.1021/ja00308a049

upstream raw materials:

4-Ketopimelic acid

heptane-1,4,7-triol

3-(5-oxo-tetrahydro-furan-2-yl)-propionic acid ethyl ester

Diisopropyl γ-hydroxypimelate

Downstream raw materials:

(+/-)-methyl γ-butyrolactone-γ-propionate

γ-(Z)-dec-7-enlactone

(R)-(+)-γ-jasmolactone

(S)-(-)-γ-jasmolactone

Refernces

• 1、 Grayson, David H.,McCarthy, Una,Roycroft, Edwin D.. "Intramolecular acylative ring-switching reactions of 3-(tetrahydro-2′-furyl)propanoic acid derivatives to give butanolides: Mechanism and scope". . p. 1930 - 1937. Retrieved 2007/10/03.
• 2、 Missio,Comasseto. "Enantioselective synthesis of (-)-γ-jasmolactone". . p. 4609 - 4615. Retrieved 2007/10/03.