117076-42-3

Basic information

• Product Name: 2-Propenoic acid, 3-[4-(chlorocarbonyl)phenyl]-, methyl ester, (2E)-
• CAS NO: 117076-42-3
• Molecular Formula: C11H9ClO3
• Molecular Weight: 224.644
• Mol File: 117076-42-3.mol

Chemical Properties

• CAS DataBase Reference: 2-Propenoic acid, 3-[4-(chlorocarbonyl)phenyl]-, methyl ester, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 3-[4-(chlorocarbonyl)phenyl]-, methyl ester, (2E)-(117076-42-3)
• EPA Substance Registry System: 2-Propenoic acid, 3-[4-(chlorocarbonyl)phenyl]-, methyl ester, (2E)-(117076-42-3)

Safety Data

• Hazardous Substances Data: 117076-42-3(Hazardous Substances Data)

Upstream product

• 115974-97-5 methyl (E)-4-carboxyl cinnamate 
• 619-66-9 4-Carboxybenzaldehyde 
• 456-25-7 p-carboxyphenyl diazonium tetrafluoroborate 

Relevant articles and documents

Design, synthesis and biological evaluation of quinoline derivatives as HDAC class I inhibitors

Inhibition of histone deacetylase (HDAC) has been regarded as a potential therapeutic approach for treatment of multiple diseases including cancer. Based on pharmacophore model of HDAC inhibitors, a series of quinoline-based N-hydroxycinnamamides and N-hydroxybenzamides were designed and synthesized as potent HDAC inhibitors. All target compounds were evaluated for their in?vitro HDAC inhibitory activities and anti-proliferative activities and the best compound 4a surpass Vorinostat in both enzymatic inhibitory activity and cellular anti-proliferative activity. In terms of HDAC isoforms selectivity, compounds 4a exhibited preferable inhibition for class I HDACs, especially for HDAC8, the IC50 value (442?nM) was much lower than that of Vorinostat (7468?nM). Subsequently, we performed class I & IIa HDACs whole cell enzyme assay to evaluate inhibitory activity in whole cell context. Compounds 4a and 4e displayed much better cellular activity for class I HDACs than that for class IIa HDACs, which indicated that 4a and 4e might be potent class I HDAC inhibitors. Meanwhile, flow cytometry analysis showed that compound 4a and 4e can promote cell apoptosis in?vitro.

Palladium-Catalyzed, ortho-Selective C-H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides

A palladium-catalyzed, ortho-selective C-H halogenation methodology is reported herein. The highlight of the work is the highly selective C(sp2)-H functionalization of benzyl nitriles in the presence of activated C(sp3)-H bond, which results in good yields of the halogenated products with excellent regioselectivity. Along with benzyl nitriles, aryl Weinreb amides and anilides have been evaluated for the transformation using aprotic conditions. Mechanistic studies yield interesting aspects with respect to the pathway of the reaction and the directing group abilities.

A New Series of Highly Potent Non-Peptide Bradykinin B2 Receptor Antagonists Incorporating the 4-Heteroarylquinoline Framework. Improvement of Aqueous Solubility and New Insights into Species Difference

Introduction of nitrogen-containing heteroaromatic groups at the 4-position of the quinoline moiety of our non-peptide B2 receptor antagonists resulted in enhancing binding affinities for the human B 2 receptor and reducing binding affinities for the guinea pig one, providing new structural insights into species difference. A CoMFA study focused on the diversity of the quinoline moiety afforded correlative and predictive QSAR models of binding for the human B2 receptor but not for the guinea pig one. A series of 4-(1-imidazolyl)quinoline derivatives could be dissolved in a 5% aqueous solution of citric acid up to a concentration of 10 mg/mL. A representative compound 48a inhibited the specific binding of [ 3H]BK to the cloned human B2 receptor expressed in Chinese hamster ovary cells with an IC50 value of 0.26 nM and significantly inhibited BK-induced bronchoconstriction in guinea pigs even at 1 μg/kg by intravenous administration.

Synthesis of unsymmetrical divinylbenzenes by palladium catalyzed sequential heck reactions starting from carboxybenzenediazonium salts

Six p-, m- and o-unsymmetrical divinylbenzenes 5a, 5b, 6a, 6b, 6c and 7a are synthesized from p-, m- and o- carboxybenzenediazonium tetrafluoroborates via sequential Heck reactions in good overall yield.

Intramolecular Cycloaddition Reactions with Azomethine Ylides: Synthesis and NMR Investigations of Some Macrolide-Type Paracyclophanes

Several aziridine derivatives bearing a para-substituted phenyl group have been prepared as precursors of azomethine ylides for intramolecular 1,3-dipolar cycloadditions.Upon heating in refluxing toluene, the expected reactions take place resulting in the