methyl (E)-5-hydroxypent-2-enoate

Base Information

• Chemical Name: methyl (E)-5-hydroxypent-2-enoate
• CAS No.: 62592-80-7
• Molecular Formula: C6H10O3
• Molecular Weight: 130.1418
• NSC Number: 266089
• Nikkaji Number: J1.762.903D
• Mol file: 62592-80-7.mol

Synonyms:methyl (E)-5-hydroxypent-2-enoate;62592-80-7;(2E)-5-Hydroxy-2-pentenoic Acid Methyl Ester;NSC266089;SCHEMBL13408037;NSC-266089;(E)-5-Hydroxy-2-pentenoic acid methyl ester;A934920

Chemical Property of methyl (E)-5-hydroxypent-2-enoate

Chemical Property:

• Vapor Pressure: 0.0386mmHg at 25°C
• Boiling Point: 212.5°C at 760 mmHg
• Flash Point: 87.5°C
• PSA: 46.53000
• Density: 1.065g/cm³
• LogP: 0.09800
• Storage Temp.: Refrigerator
• Solubility.: Ethyl Acetate, Methanol
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 130.062994177
• Heavy Atom Count: 9
• Complexity: 107

Purity/Quality:

99% ^*data from raw suppliers

(2E)-5-Hydroxy-2-pentenoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C=CCCO
• Isomeric SMILES: COC(=O)/C=C/CCO
• Uses: (2E)-5-Hydroxy-2-pentenoic Acid Methyl Ester is an intermediate in the preparation of unusual amino acids that are potential Michael acceptor based antiplasmodial and antitrypanosomal cysteine protease inhibitors.

Technology Process of methyl (E)-5-hydroxypent-2-enoate

There total 3 articles about methyl (E)-5-hydroxypent-2-enoate 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: 90.0%

(E)-methyl 5-[(tert-butyldimethylsilyl)oxy]pent-2-enoate (688801-64-1) → methyl trans-5-hydroxy-2-pentenoate (62592-80-7)

Guidance literature:

With hydrogen fluoride; In tetrahydrofuran; water; at 20 ℃; for 6h;

DOI:10.1016/j.tetlet.2009.03.145

Reference yield: 66.0%

methyl (2E)-5-(4-methoxybenzyloxy)-2-pentenoate (201667-72-3) → methyl trans-5-hydroxy-2-pentenoate (62592-80-7)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; at 20 ℃; for 1h;

DOI:10.1002/1099-0690(200206)2002:12<1941::AID-EJOC1941>3.0.CO;2-T

Reference yield: 55.0%

(methyloxycarbonylmethyl)triphenylphosphonium bromide (1779-58-4) + trimethyleneglycol (504-63-2) → methyl trans-5-hydroxy-2-pentenoate (62592-80-7)

Guidance literature:

(methyloxycarbonylmethyl)triphenylphosphonium bromide; With triethylamine; In dichloromethane; at 20 ℃; for 0.0833333h;

trimethyleneglycol; With manganese(IV) oxide; In dichloromethane; at 20 ℃; for 24h; Concentration;

DOI:10.1021/acs.joc.1c00580

upstream raw materials:

methyl (2E)-5-(4-methoxybenzyloxy)-2-pentenoate

(E)-methyl 5-[(tert-butyldimethylsilyl)oxy]pent-2-enoate

(methyloxycarbonylmethyl)triphenylphosphonium bromide

trimethyleneglycol

Downstream raw materials:

methyl (E)-5-bromo-2-pentenoate

3-methylene-2-pent-4-enyl-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indole

N-(p-toluenesulfonyl)-2-(3-(methoxycarbonyl)propyl)-3-methylene-2,3-dihydroindole

N-(4-(methoxycarbonyl)-1-butenyl)-N-(p-toluenesulfonyl)-2-ethenylaniline

Refernces

• 1、 English, Brandon J.,Williams, Robert M.. "Synthesis of (±)-oleocanthal via a tandem intramolecular Michael cyclization-HWE olefination". experimental part. p. 2713 - 2715. Retrieved 2009/09/06.