5676-62-0

Upstream product

• 1615-02-7 3-(4-chlorophenyl)prop-2-enoic acid 
• 104-88-1 4-chlorobenzaldehyde 
• 873-73-4 4-n-chlorophenylacetylene 
• 3240-10-6 (4-chlorophenyl)propiolic acid 
• 63757-30-2 ethyl (Z)-3-(4-chlorophenyl)acrylate 
• 20026-96-4 ethyl 3-(4-chlorophenyl)propiolate 
• 20754-24-9 methyl (Z)-3-(p-chlorophenyl)prop-2-enoate 
• 31357-32-1 α,β-dibromo-p-chlorohydrocinnamic acid 
• 24653-99-4 (2RS,3SR)-2,3-dibromo-3-(4-chlorophenyl)propanoic acid 
• 201230-82-2 carbon monoxide 
• 66482-30-2 (Z)-1-bromo-2-(4-chlorophenyl)ethylene 

Downstream Products

• 81509-26-4 p-chloro-phenyl-3 endo bicyclo<2.2.1> heptene-5 carboxylate endo-2 de methyle 
• 81509-29-7 p-Cl-phenyl-3 endo bicyclo<2.2.1>heptane carbolactone 2-6 
• 59259-40-4 acide p-chloro phenyl-3 endo bicyclo<2.2.1>heptene-5 carboxylique-2 endo 
• 18684-82-7 Z-1-chloro-4-(2-chloroethenyl)benzene 
• 59259-40-4 acide p-chloro phenyl-3 exo bicyclo<2.2.1> heptene-5 carboxylique-2 exo 
• 81509-21-9 (1S,3S,6S,7R,9R)-9-(4-Chloro-phenyl)-2-iodo-4-oxa-tricyclo[4.2.1.0^3,7]nonan-5-one 
• 34576-85-7 3,6-Dichlor-benzo--thiophen-2-carbonsaeurechlorid 

Relevant academic research and scientific papers

Understanding the role played by protic ionic liquids (PILs) and the substituent effect for enhancing the generation of: Z-cinnamic acid derivatives

Photoisomerization of a series of substituted E-cinnamic acids in MeCN in their acid forms and as their corresponding protic ionic liquids (PILs) with light of 300 nm is studied. The nature, strength, number, and position effects of substituents on the photochemical behavior of E-cinnamic derivatives are investigated. The photosensitization of the reaction in the presence of Michler's ketone is also studied at 366 nm and it demonstrates that the triplet-excited state is involved in the reaction. As the presence of n-butylamine needed to form the PILs significantly increases the photoproduct yields in all cases, the role of the PILs is also discussed. Thus, understanding of these fundamental aspects has allowed us to establish an excellent and practical synthetic protocol for successfully synthesizing Z-cinnamic acids. This journal is

Semireduction of alkynoic acids via a transition metal-free α borylation-protodeborylation sequence

A method for the semi-reduction of alkynoic acids through an α-borylation and subsequent protodeborylation mechanism has been developed. The transition metal-free protocol is achieved through the activation of bis(pinacolato)diboron by an in situ generated carboxylate moiety yielding aryl acrylic acids. Our studies demonstrate an unprecedented dual role for the carboxylate anion that involves the activation of the diboron reagent and a directing effect in the α-borylation.

Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors

1-O-cis-Cinnamoyl-β-d-glucopyranose is one of the most potent allelochemicals that has been isolated from Spiraea thunbergii Sieb by Hiradate et al. It derives its strong inhibitory activity from cis-cinnamic acid (cis-CA), which is crucial for phytotoxicity. By preparing and assaying a series of cis-CA analogues, it was previously found that the key features of cis-CA for lettuce root growth inhibition are a phenyl ring, cis-configuration of the alkene moiety, and carboxylic acid. On the basis of a structure-activity relationship study, the substituent effects on the aromatic ring of cis-CA were examined by systematic synthesis and the lettuce root growth inhibition assay of a series of cis-CA analogues having substituents on the aromatic ring. While ortho- and para-substituted analogues exhibited low potency in most cases, meta-substitution was not critical for potency, and analogues having a hydrophobic and sterically small substituent were more likely to be potent. Finally, several cis-CA analogues were found to be more potent root growth inhibitors than cis-CA.

A linear solvation energy relationship study for the reactivity of 2-(4-substituted phenyl)-cyclohe-1-enecarboxylic, 2-(4-substituted phenyl)-benzoic, and 2-(4-substituted phenyl)-acrylic acids with diazodiphenylmethane in various solvents

The reactivities of 2-(4-substituted phenyl)-cyclohex-1-enecarboxylic acids, 2-(4-substituted phenyl)-benzoic acids, and 2-(4-substituted phenyl)-acrylic acids with diazodiphenylmethane in various solvents were investigated. To explain the kinetic results through solvent effects, the second-order rate constants of the examined acids were correlated using the Kamlet-Taft solvatochromic equation. The correlations of the kinetic data were carried out by means of multiple linear regression analysis, and the solvent effects on the reaction rates were analyzed in terms of initial and transition state contributions. The signs of the equation coefficients support the proposed reaction mechanism. The solvation models for all investigated carboxylic acids are suggested. The quantitative relationship between the molecular structure and the chemical reactivity is discussed, as well as the effect of geometry on the reactivity of the examined molecules.

Dimethyl sulfoxide mediated elimination reactions in 3-aryl 2,3-dihalopropanoates: Scope and mechanistic insights

(Chemical Equation Presented) Dimethyl sulfoxide (DMSO) efficiently causes the reductive elimination of 3-aryl 2,3-dibromopropanoates to cinnamates with good yield. With 3-phenyl 2,3-dihalopropanoates, debromination is the major pathway providing 3-phenylacrylate derivatives in high yields, whereas dehydrobromination is a competing pathway with thiophene derivatives. 1H NMR, 81Br NMR, and MS techniques indicated the formation of brominated-DMSO, MeBr, and HBr as byproducts in this transformation with no evidence for the formation of Br2. The dual role of DMSO as a nucleophile and bromine scavenger accounts for the products formed in this reaction.

Novel cinnamic amides

E-cinnamic amides of piperazine derivatives according to formula (I) wherein X is chloro or fluoro and R1 is an aromatic or heteroaromatic group, their pharmaceutically acceptable salts or solvates. The invention also relates to pharmaceutical

Synthesis and pharmacology of site-specific cocaine abuse treatment agents: 2-(Aminomethyl)-3-phenylbicyclo [2.2.2]- and - [2.2.1] alkane dopamine uptake inhibitors

As part of a program to develop site-specific medications for cocaine abuse, a series of 2-(aminomethyl)-3-phenylbicyclo[2.2.2]- and -[2.2.1]alkane derivatives was synthesized and tested for inhibitory potency in [3H]WIN 35,428 binding and [3H]dopamine uptake assays using rat striatal tissue. Selected compounds were tested for their ability to substitute for cocaine in rat drug discrimination tests. Synthesis was accomplished by a series of Diels-Alder reactions, using cis- and trans-cinnamic acid derivatives (nitrile, acid, acid chloride) with cyclohexadiene and cyclopentadiene. Standard manipulations produced the aminomethyl side chain. Many of the compounds bound with high affinity (median IC50 = 223 nM) to the cocaine binding site as marked by [3H]WIN 35,428. Potency in the binding assay was strongly enhanced by chlorine atoms in the 3- and/or 4-position on the aromatic ring and was little affected by corresponding methoxy groups. In the [2.2.2] series there was little difference in potency between cis and trans compounds or between N,N-dimethylamines and primary amines. In the [2.2.1] series the trans exo compounds tended to be least potent against binding, whereas the cis exo compounds were the most potent (4-Cl cis exo: IC50 = 7.7 nM, 27-fold more potent than 4-Cl trans-exo). Although the potencies of the bicyclic derivatives in the binding and uptake assays were highly correlated, some of the compounds were 5-7-fold less potent at inhibiting [3H]-dopamine uptake than [3H]WIN 35,428 binding (for comparison, cocaine has a lower discrimination ratio (DR) of 2.5). The DR values were higher for almost all primary amines and for the trans-[2.2.2] series as compared to the cis-[2.2.2]. Most of the compounds had Hill coefficients approaching unity, except for the [2.2.2] 3,4-dichloro derivatives, which all had n(H) values of about 2.0. Two of the compounds were shown to fully substitute for cocaine in drug discrimination tests in rats, and one had a very long duration of action.

Analogues of Capsaicin with Agonist Activity as Novel Analgesic Agents; Structure-Activity Studies. 3. The Hydrophobic Side-Chain "C-Region"

Structural variants of the hydrophobic side chain ("C region") of the capsaicin molecule have been incorporated into a series of vanillylamides and vanillylthioureas.These compounds have been tested in an in vitro assay for agonism (45Ca2+ infl

A CONVENIENT METHOD FOR THE CONVERSION OF trans to cis-CINNAMIC ACIDS

trans-Cinnamic acids react in sequence with bromine, base, and carbon monoxide to give cis-acids in reasonable yields.