1643-28-3

Usage

Chemical Properties

White powder

InChI:InChI=1/C9H9ClO2/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-4H,5-6H2,(H,11,12)/p-1

Upstream product

• 3752-25-8 o-chlorocinnamic acid 
• 77738-21-7 diethyl 2-(2-chlorobenzyl)malonate 
• 704-96-1 trans-2-chlorocinnamic acid 
• 7315-17-5 3-(2-chloro-phenyl)-propionitrile 
• 107-94-8 chloropropionic acid 
• 108-90-7 chlorobenzene 
• 30573-88-7 ethyl 3-(2-chlorophenyl)propanoate 
• 2033-24-1 cycl-isopropylidene malonate 
• 89-98-5 2-chloro-benzaldehyde 
• 10034-85-2 hydrogen iodide 
• 704-96-1 (Z)-3-(2-chlorophenyl)acrylic acid 
• 95-49-8 2-methylchlorobenzene 
• 611-19-8 1-chloro-2-(chloromethyl)benzene 
• 2444-36-2 2'-chloro-benzeneacetic acid 

Downstream Products

• 495-78-3 3-(2-hydroxyphenyl)propionic acid 
• 52085-97-9 3-(2-chlorophenyl)propionyl chloride 
• 74124-86-0 3-chlorophenylpropionic acid methyl ester 
• 177172-48-4 (R)-3-(2-chlorophenyl)-N-(1-(3'-methoxyphenyl)ethyl)propanamide 
• 3199-71-1 4-chloro-2,3-dihydro-1H-inden-1-ol 
• 15115-59-0 4-chloro-2,3-dihydro-1H-inden-1-one 
• 67120-40-5 4-chloroindane-1-amine 
• 836612-33-0 2-chloro-N-(2,6-dichloro-5-quinolinyl)-benzenepropanamide 
• 3199-69-7 2-bromo-4-chloro-1-indanone 
• 1266727-72-3 (R)-3-(2-chlorophenyl)-N-(1-phenylethyl)propanamide 
• 1266727-75-6 (R)-3-(2-chlorophenyl)-N-(1-phenylethyl)propylamine 
• 1266727-80-3 3-(2-chlorophenyl)-N-(1-(3'-methoxyphenyl)ethyl)propanamide 
• 199325-86-5 3-(2-chlorophenyl)-N-(1-phenylethyl)propanamide 
• 157433-36-8 3-(2-chlorophenyl)propanal 

Relevant academic research and scientific papers

Characterization of a carbon-carbon hydrolase from Mycobacterium tuberculosis involved in cholesterol metabolism

In the recently identified cholesterol catabolic pathway of Mycobacterium tuberculosis, 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase (HsaD) is proposed to catalyze the hydrolysis of a carbon-carbon bond in 4,5-9,10-diseco-3-hydroxy-5,9,17-tri-oxoandrosta-1 (10),2-diene-4-oic acid (DSHA), the cholesterol meta-cleavage product (MCP) and has been implicated in the intracellular survival of the pathogen. Herein, purified HsaD demonstrated 4-33 times higher specificity for DSHA (kcat/Km = 3.3 ± 0.3 × 104 M-1 s-1) than for the biphenyl MCP 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid (HOPDA) and the synthetic analogue 8-(2-chlorophenyl)-2-hydroxy-5-methyl-6-oxoocta-2, 4-dienoic acid (HOPODA), respectively. The S114A variant of HsaD, in which the active site serine was substituted with alanine, was catalytically impaired and bound DSHA with a Kd of 51 ± 2 μM. The S114A·DSHA species absorbed maximally at 456 nm, 60 nm red-shifted versus the DSHA enolate. Crystal structures of the variant in complex with HOPDA, HOPODA, or DSHA to 1.8 -1.9 A indicate that this shift is due to the enzyme-induced strain of the enolate. These data indicate that the catalytic serine catalyzes tautomerization. A second role for this residue is suggested by a solvent molecule whose position in all structures is consistent with its activation by the serine for the nucleophilic attack of the substrate. Finally, the α-helical lid covering the active site displayed a ligand-dependent conformational change involving differences in side chain carbon positions of up to 6.7 A, supporting a two-conformation enzymatic mechanism. Overall, these results provide novel insights into the determinants of specificity in a mycobacterial cholesterol-degrading enzyme as well as into the mechanism of MCP hydrolases.

Discovery of Novel UDP- N-Acetylglucosamine Acyltransferase (LpxA) Inhibitors with Activity against Pseudomonas aeruginosa

This study describes a novel series of UDP-N-acetylglucosamine acyltransferase (LpxA) inhibitors that was identified through affinity-mediated selection from a DNA-encoded compound library. The original hit was a selective inhibitor of Pseudomonas aeruginosa LpxA with no activity against Escherichia coli LpxA. The biochemical potency of the series was optimized through an X-ray crystallography-supported medicinal chemistry program, resulting in compounds with nanomolar activity against P. aeruginosa LpxA (best half-maximal inhibitory concentration (IC50) 20 μM and MIC > 128 μg/mL). The mode of action of analogues was confirmed through genetic analyses. As expected, compounds were active against multidrug-resistant isolates. Further optimization of pharmacokinetics is needed before efficacy studies in mouse infection models can be attempted. To our knowledge, this is the first reported LpxA inhibitor series with selective activity against P. aeruginosa.

Method for synthesizing phenylpropionic acid compounds through heterogeneous palladium metal catalysis

The invention discloses a method for synthesizing phenylpropionic acid compounds by heterogeneous catalysis. The method comprises the following steps: sequentially adding Pd@POL, toluene, styrene, formic acid and acetic anhydride into a reaction flask, stirring the reaction mixture at 80 DEG C to react, cooling the reaction solution to room temperature after the reaction is finished, diluting with dichloromethane, and transferring the solution into a separating funnel, washing with a sodium hydroxide solution, acidifying the water layer with a hydrochloric acid aqueous solution, extracting with dichloromethane, merging organic phases, drying with anhydrous sodium sulfate, and carrying out vacuum concentration to obtain the phenylpropionic acid compound. The method can remove heavy metal residues, is green and environment-friendly, is simple to operate and easy to implement, and the prepared phenylpropionic acid compound has a good application prospect.

Harnessing Applied Potential: Selective β-Hydrocarboxylation of Substituted Olefins

The construction of carboxylic acid compounds in a selective fashion from low value materials such as alkenes remains a long-standing challenge to synthetic chemists. In particular, β-addition to styrenes is underdeveloped. Herein we report a new electrosynthetic approach to the selective hydrocarboxylation of alkenes that overcomes the limitations of current transition metal and photochemical approaches. The reported method allows unprecedented direct access to carboxylic acids derived from β,β-trisubstituted alkenes, in a highly regioselective manner.

Cyclohexyl-Fused, Spirobiindane-Derived, Phosphine-Catalyzed Synthesis of Tricyclic ?3-Lactams and Kinetic Resolution of ?3-Substituted Allenoates

A C2-symmetric chiral phosphine catalyst, NUSIOC-Phos, which can be easily derived from cyclohexyl-fused spirobiindane, was introduced. A highly enantioselective domino process involving pyrrolidine-2,3-diones and γ-substituted allenoates catalyzed by NUSIOC-Phos has been disclosed. Diastereospecific tricyclic γ-lactams containing five contiguous stereogenic centers were obtained in high yields and with nearly perfect enantioselectivities. A kinetic resolution process of racemic γ-substituted allenoates was developed for the generation of optically enriched chiral allenoates.

Synthesis of N-Substituted Condensed Tetrahydropyridine-Based Enaminones via Palladium-Catalyzed Intramolecular C–N Cross-coupling

A number of β-enaminones with secondary amino group (alkyl, cyclopropyl, and aryl) were prepared from corresponding β-diketones. Two general protocols for their palladium-catalyzed intramolecular C–N cross-coupling were established to give corresponding N-substituted condensed tetrahydropyridines in good yields. The methodology is applicable for a wide variety of structural motifs. The work also extends the applicability of novel, recently established, palladium precatalysts to new substrates.

Regioselectivity inversion tuned by iron(iii) salts in palladium-catalyzed carbonylations

Impactful regioselectivity control is crucial for cost-effective chemical synthesis. By using cheap and abundant iron(iii) salts, the hydroxycarbonylations of both aromatic and aliphatic alkenes were significantly enhanced in both reactivity and selectivity (iso/n or n/iso up to >99:1). Moreover, Pd-catalyzed carbonylation selectivity can be switched from branched to linear by using different Fe(iii) salts. In addition, similar results were obtained for the carbonylation of secondary alcohols.

A Ligand-Directed Catalytic Regioselective Hydrocarboxylation of Aryl Olefins with Pd and Formic Acid

An effective Pd-catalyzed hydrocarboxylation of aryl olefins with Ac2O and formic acid is described. A variety of 2- and 3-arylpropanoic acids can be regioselectively formed by the judicious choice of ligand without the use of toxic CO gas.

An intramolecular C-N cross-coupling of β-enaminones: A simple and efficient way to precursors of some alkaloids of Galipea officinalis

2-Aroylmethylidene-1,2,3,4-tetrahydroquinolines with the appropriate substituents can be suitable precursors for the synthesis of alkaloids from Galipea officinalis (cuspareine, galipeine, galipinine, angustureine). However, only two, rather low-yielding procedures for their synthesis are described in the literature. We have developed a simple and efficient protocol for an intramolecular, palladium or copper-catalysed amination of both chloro- and bromo-substituted 3-amino-1,5-diphenylpent-2-en-1-ones leading to the above-mentioned tetrahydroquinoline moiety. The methodology is superior to the methods published to date.

Simultaneous control of regioselectivity and enantioselectivity in the hydroxycarbonylation and methoxycarbonylation of vinyl arenes

Using a family of novel mononuclear and dinuclear palladium complexes of phanephos ligands, the simultaneous control of regioselectivity and enantioselectivity in the hydroxycarbonylation and alkoxycarbonylation of styrene derivatives has been realised for the first time. The Royal Society of Chemistry 2013.