29743-74-6

Basic information

• Product Name: 2-Pentenoic acid, 3-phenyl-, ethyl ester, (Z)-
• CAS NO: 29743-74-6
• Molecular Formula: C13H16O2
• Molecular Weight: 204.269
• Mol File: 29743-74-6.mol

Chemical Properties

• CAS DataBase Reference: 2-Pentenoic acid, 3-phenyl-, ethyl ester, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pentenoic acid, 3-phenyl-, ethyl ester, (Z)-(29743-74-6)
• EPA Substance Registry System: 2-Pentenoic acid, 3-phenyl-, ethyl ester, (Z)-(29743-74-6)

Safety Data

• Hazardous Substances Data: 29743-74-6(Hazardous Substances Data)

Upstream product

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 93-55-0 1-phenyl-propan-1-one 
• 2293-61-0 ethyl 3-hydroxy-3-phenylpentanoate 
• 55314-57-3 ethyl pent-2-ynoate 
• 98-80-6 phenylboronic acid 
• 18819-66-4 (Z)-3-chloro-3-phenyl-2-propenoic acid 
• 18819-63-1 (E)-3-chloro-3-phenyl-2-propenoic acid 
• 183614-20-2 1-(1,2,4-triazol-1-yl)-3-phenylpropargyl ethyl ether 
• 6142-95-6 phenylpropargyl aldehyde diethyl acetal 
• 55164-20-0 ethyl-(E)-3-chloro-3-phenyl-2-propenoate 
• 925-90-6 ethylmagnesium bromide 
• 55164-19-7 ethyl-(Z)-3-chloro-3-phenyl-2-propenoate 
• 185987-41-1 (Z)-3-Phenyl-3-phenyltellanyl-acrylic acid ethyl ester 
• 623-51-8 ethyl 2-sulfanylacetate 

Downstream Products

• 1448857-08-6 (Z)-1,3-diphenylpent-2-en-1-one 
• 1448857-48-4 1-(4-methoxyphenyl)-3-methyl-3-phenylpentan-1-one 
• 4887-10-9 (R)-3-methyl-3-phenylpentanoic acid 
• 1448857-21-3 (E)-1-(4-methoxyphenyl)-3-phenylpent-2-en-1-one 
• 1448857-22-4 (E)-1-(4-chlorophenyl)-3-phenylpent-2-en-1-one 
• 1448857-47-3 1-(4-methoxyphenyl)-3-methyl-3-phenylpentan-1-one 
• 1528-58-1 (Z)-3-phenyl-2-pentenoic acid 
• 1376710-87-0 (E)-N-methoxy-N-methyl-3-phenylpent-2-enamidee 
• 384333-59-9 (E)-3-phenyl-pent-2-en-1-ol 
• 1446100-85-1 3-ethyl-5,6-dimethoxy-3-phenylindan-1-one 
• 36872-11-4 β-Ethyl-cinnamaldehyde 
• 36872-10-3 (Z)-3-phenyl-2-pentenal 

Relevant articles and documents

Energy-Transfer-Mediated Photocatalysis by a Bioinspired Organic Perylenephotosensitizer HiBRCP

Energy transfer plays a special role in photocatalysis by utilizing the potential energy of the excited state through indirect excitation, in which a photosensitizer determines the thermodynamic feasibility of the reaction. Bioinspired by the energy-transfer ability of natural product cercosporin, here we developed a green and highly efficient organic photosensitizer HiBRCP (hexaisobutyryl reduced cercosporin) through structural modification of cercosporin. After structural manipulation, its triplet energy was greatly improved, and then, it could markedly promote the efficient geometrical isomerization of alkenes from the E-isomer to the Z-isomer. Moreover, it was also effective for energy-transfer-mediated organometallic catalysis, which allowed realization of the cross-coupling of aryl bromides and carboxylic acids through efficient energy transfer from HiBRCP to nickel complexes. Thus, the study on the relationship between structural manipulation and their photophysical properties provided guidance for further modification of cercosporin, which could be applied to more meaningful and challenging energy-transfer reactions.

Heteroleptic Copper-Based Complexes for Energy-Transfer Processes: E → Z Isomerization and Tandem Photocatalytic Sequences

Energy-transfer processes involving copper complexes are rare. Using an optimized heteroleptic copper complex, Cu(bphen)(XantPhos)BF4, photosensitized E → Z isomerization of olefins is demonstrated. The XantPhos ligand afforded sensitizers with improved catalyst stability, while the bphen ligand lengthened the excited-state lifetime. A series of 25 di- and trisubstituted alkenes underwent photoisomerization, including macrocycles and 1,3-enynes. Cu(bphen)(XantPhos)BF4 could also be employed in a tandem ATRA/photoisomerization process employing arylsulfonyl chlorides, an example of photoisomerization with halide-substituted olefins.

Copper-Photocatalyzed Contra-Thermodynamic Isomerization of Polarized Alkenes

The contra-thermodynamic isomerization of α- and β-substituted cinnamate derivatives catalyzed by the Cu(OAc)2/rac-BINAP complex under blue light irradiation is reported. The use of an oxazolidinone template, which favored the complexation of the copper catalyst to the substrate, allowed the E → Z isomerization of the catalytically formed chromophore under simple and robust reaction conditions in good to excellent ratios. The mechanism of this process based on the transient formation of a chromophore was also studied.

Anti-Hydroarylation of Activated Internal Alkynes: Merging Pd and Energy Transfer Catalysis

A general catalytic anti-hydroarylation of electron-deficient internal alkynes compatible with both electron-poor and electron-rich aryl reagents is reported. This selectivity is achieved through a sequential syn-carbopalladation of the alkyne by an Ar-Pd species, followed by a tandem, Ir-photocatalyzed, counter-thermodynamic E → Z isomerization. The use of ortho-substituted boronic acids enables direct access to pharmaceutically relevant heterocyclic cores via a cascade process. Mechanistic insight into the involvement of Ar-Pd versus Pd-H as an active species is provided.

Enantioselective epoxidation of β,β-disubstituted enamides with a manganese catalyst and aqueous hydrogen peroxide

Enantioselective epoxidation of β,β-disubstituted enamides with aqueous hydrogen peroxide and a novel manganese catalyst is described. Epoxidation is stereospecific and proceeds fast under mild conditions. Amides are disclosed as key functional groups to enable high enantioselectivity.

Highly Selective and Catalytic Generation of Acyclic Quaternary Carbon Stereocenters via Functionalization of 1,3-Dienes with CO2

The catalytic asymmetric functionalization of readily available 1,3-dienes is highly important, but current examples are mostly limited to the construction of tertiary chiral centers. The asymmetric generation of acyclic products containing all-carbon quaternary stereocenters from substituted 1,3-dienes represents a more challenging, but highly desirable, synthetic process for which there are very few examples. Herein, we report the highly selective copper-catalyzed generation of chiral all-carbon acyclic quaternary stereocenters via functionalization of 1,3-dienes with CO2. A variety of readily available 1,1-disubstituted 1,3-dienes, as well as a 1,3,5-triene, undergo reductive hydroxymethylation with high chemo-, regio-, E/Z-, and enantioselectivities. The reported method features good functional group tolerance, is readily scaled up to at least 5 mmol of starting diene, and generates chiral products that are useful building blocks for further derivatization. Systemic mechanistic investigations using density functional theory calculations were performed and provided the first theoretical investigation for an asymmetric transformation involving CO2. These computational results indicate that the 1,2-hydrocupration of 1,3-diene proceeds with high π-facial selectivity to generate an (S)-allylcopper intermediate, which further induces the chirality of the quaternary carbon center in the final product. The 1,4-addition of an internal allylcopper complex, which differs from previous reports involving terminal allylmetallic intermediates, to CO2 kinetically determines the E/Z- and regioselectivity. The rapid reduction of a copper carboxylate intermediate to the corresponding silyl-ether in the presence of Me(MeO)2SiH provides the exergonic impetus and leads to chemoselective hydroxymethylation rather than carboxylation. These results provide new insights for guiding further development of asymmetric C-C bond formations with CO2

Spatiotemporal Control of Pre-existing Alkene Geometry: A Bio-Inspired Route to 4-Trifluoromethyl-2H-chromenes

Routes to prepare C4-trifluoromethyl analogues of the 2H-chromene scaffold are scarce: this is particularly striking given the importance of fluorine in pharmaceutical development. To address this limitation, a facile strategy has been developed that is reliant on catalytic, geometric isomerization of easily accessible allylic alcohols (up to >95:5) followed by intramolecular cyclization via Pd catalysis (up to 96%). This concise biomimetic approach emulates the photoisomerization/cyclization cascade inherent to phenylpropanoid biosynthesis.

Rh-Catalyzed Asymmetric Hydrogenation of β-Branched Enol Esters for the Synthesis of β-Chiral Primary Alcohols

An asymmetric hydrogenation of β-branched enol esters has been developed for the first time, providing a new route for the synthesis of β-chiral primary alcohols. Using a (S)-SKP-Rh complex bearing a large bite angle and enol ester substrates possessing an O-fomyl directing group, the desired products were obtained in quantitative yields and with excellent enantioselectivities.

Copper(i)-catalysed asymmetric allylic reductions with hydrosilanes

A copper(i)-catalysed asymmetric allylic reduction enables a regio- and stereoselective transfer of a hydride nucleophile in an SN2′-fashion onto allylic bromides. This transformation represents a conceptually orthogonal approach to allylic substitution reactions with carbon nucleophiles. A copper(i) complex based upon a chiral N-heterocyclic carbene (NHC) ligand allows for stereoselectivity reaching 99% ee. The catalyst enables a stereoconvergent reaction irrespective of the double bond configuration of the starting materials.

Pd(II)/Bipyridine-Catalyzed Conjugate Addition of Arylboronic Acids to α,β-Unsaturated Carboxylic Acids. Synthesis of β-Quaternary Carbons Substituted Carboxylic Acids

Pd(II)/bipyridine-catalyzed conjugate addition of arylboronic acids to α,β-unsaturated carboxylic acids (including β,β-disubstituted acrylic acids) was developed and optimized, which provided a mild and convenient method for the highly challenging synthesis of β-quaternary carbons substituted carboxylic acids.