2-Acetylamino-3-(3,4-dichloro-phenyl)-acrylic acid

Base Information

• Chemical Name: 2-Acetylamino-3-(3,4-dichloro-phenyl)-acrylic acid
• CAS No.: 14091-10-2
• Molecular Formula: C11H9Cl2NO3
• Molecular Weight: 241.674
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID00372638
• Mol file: 14091-10-2.mol

Synonyms:2-acetylamino-3-(3,4-dichloro-phenyl)-acrylic acid;2-acetamido-3-(3,4-dichlorophenyl)prop-2-enoic acid;14091-10-2;2-ACETYLAMINO-3-(3,4-DICHLOROPHENYL)ACRYLIC ACID;Maybridge4_004628;DTXSID00372638;HSYXRTFLJZJGAM-UHFFFAOYSA-N

Chemical Property of 2-Acetylamino-3-(3,4-dichloro-phenyl)-acrylic acid

Chemical Property:

• PSA: 69.89000
• LogP: 3.39530
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 272.9959485
• Heavy Atom Count: 17
• Complexity: 344

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(=CC1=CC(=C(C=C1)Cl)Cl)C(=O)O

Technology Process of 2-Acetylamino-3-(3,4-dichloro-phenyl)-acrylic acid

There total 27 articles about 2-Acetylamino-3-(3,4-dichloro-phenyl)-acrylic 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: 100.0%

2-acetylamino-2-(4-chlorobenzyl)malonic acid diethyl ester (6941-36-2) → N-acetyl-4-chlorophenylalanine (14091-10-2)

Guidance literature:

With aqueous 48percent KOH; In ethanol; water; for 4h; Heating / reflux;

Reference yield: 81.0%

(Z)-N-(1-(4-chlorophenyl)-3-oxoprop-1-en-2-yl)acetamide → (S)-2-acetamido-3-(4-chlorophenyl)propanoic acid (14091-10-2,23434-92-6,135270-40-5,55478-55-2) + (Z)-2-acetamido-3-(4-chlorophenyl)acrylic acid (88681-63-4)

Guidance literature:

With aldehyde dehydrogenase from bovine lens; ene-reductase from Saccharomyces cerevisiae; NADH; In aq. phosphate buffer; at 30 ℃; for 5h; pH=7; Reagent/catalyst; stereoselective reaction; Enzymatic reaction;

DOI:10.1039/c4ob02282c

Reference yield: 75.0%

acetamide (60-35-5) + carbon monoxide (201230-82-2) + (4-chlorophenyl)acetaldehyde (4251-65-4) → N-acetyl-4-chlorophenylalanine (14091-10-2)

Guidance literature:

With sulfuric acid; lithium bromide; bis(triphenylphosphine)palladium dibromide; In various solvent(s); at 120 ℃; for 12h; under 45003.6 Torr;

DOI:10.1002/(SICI)1521-3765(19980515)4:5<935::AID-CHEM935>3.0.CO;2-#

upstream raw materials:

(Z)-2-acetamido-3-(4-chlorophenyl)acrylic acid

acetamide

carbon monoxide

(4-chlorophenyl)acetaldehyde

Downstream raw materials:

(S)-2-acetamido-3-(4-chlorophenyl)propanoic acid

(S)-ethyl 2-acetamido-3-(4-chlorophenyl)propanoate

methyl 2-acetylamino-3-(4-chlorophenyl)propanoate

p-chlorophenylalanine

Refernces

• 1、 Knaus, Tanja,Mutti, Francesco G.,Humphreys, Luke D.,Turner, Nicholas J.,Scrutton, Nigel S.. "Systematic methodology for the development of biocatalytic hydrogen-borrowing cascades: Application to the synthesis of chiral α-substituted carboxylic acids from α-substituted α,β-unsaturated aldehydes". supporting information. p. 223 - 233. Retrieved 2015/02/19.
• 2、 Boyd, Derek R.,Bell, Mark,Dunne, Katherine S.,Kelly, Brian,Stevenson, Paul J.,Malone, John F.,Allen, Christopher C. R.. "Chemoenzymatic synthesis of a mixed phosphine-phosphine oxide catalyst and its application to asymmetric allylation of aldehydes and hydrogenation of alkenes". experimental part. p. 1388 - 1395. Retrieved 2012/03/27.