32147-13-0

Basic information

• Product Name: 3-(4-methylphenyl)-2-butenoic acid
• Synonyms: 3-(4-methylphenyl)-2-butenoic acid
• CAS NO: 32147-13-0
• Molecular Weight: 176.215
• Mol File: 32147-13-0.mol

Chemical Properties

• CAS DataBase Reference: 3-(4-methylphenyl)-2-butenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-methylphenyl)-2-butenoic acid(32147-13-0)
• EPA Substance Registry System: 3-(4-methylphenyl)-2-butenoic acid(32147-13-0)

Safety Data

• Hazardous Substances Data: 32147-13-0(Hazardous Substances Data)

Upstream product

• 105-39-5 chloroacetic acid ethyl ester 
• 122-00-9 para-methylacetophenone 
• 107-93-7 (E)-but-2-enoic acid 
• 624-31-7 4-tolyl iodide 
• 3095-95-2 diethylphosphonoacetic acid 
• 70964-89-5 E-methyl β-methyl-p-methylcinnamate 
• 6305-61-9 ethyl (E)-3-p-tolylbut-2-enoate 

Downstream Products

• 166986-36-3 (Z)-3-(p-tolyl)but-2-enoic acid 
• 105556-74-9 methyl N-<(E)-3-p-tolyl-2-butenoyl>-(S)-prolinate 
• 947383-46-2 (E)-1-methyl-4-(1-nitroprop-1-en-2-yl)benzene 
• 14002-90-5 4,7-dimethyl-coumarin 
• 4389-57-5 3-phenyl-3-p-tolylbutanoic acid 
• 1201-85-0 (S)-3-(4-methylphenyl)butanoic acid 

Relevant articles and documents

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.

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.

Pd-Catalyzed decarboxylative cross-coupling reactions of epoxides with α,β-unsaturated carboxylic acids

A Pd-catalyzed decarboxylative cross-coupling of α,β-unsaturated carboxylic acids with cyclic and acyclic epoxides has been developed. Both β-monosubstituted and β-disubstituted unsaturated carboxylic acids, as well as conjugated diene unsaturated carboxylic acids are suitable reaction substrates. Substituted homoallylic alcohols were obtained in moderate to good yields. The product was obtained as a mixture of diastereomers favoring the anti diastereomer of the cyclic epoxides. This work provides a method for the modification of complex organic molecules containing α,β-unsaturated carboxylic acids.

DMAP-Catalyzed [4 + 2] Cycloaddition of α,β-Unsaturated Carboxylic Acids with Ketones for Synthesis of α,β-Unsaturated δ-Lactones

The DMAP-catalyzed [4 + 2] cycloaddition of α,β-unsaturated carboxylic acids with ketones furnishing α,β-unsaturated δ-lactones in good yields (up to 80%) is described, which is the first example of remote γ-C(sp3)-H activation of α,β-unsaturated carboxylic acids facilitated by DMAP, a pyridine-based catalyst. Copyright

Diastereoselective hydrogenation of α,β-unsaturated but-2-enamides to access the chiral 3-(p-tolyl) butanoic acids

An alternative methodology for the synthesis of chiral 3-(p-tolyl) butanoic acids is presented. This was accomplished through the diastereoselective hydrogenation reaction of different chiral N-3-(p-tolyl) but-2-enamides, using Pd/C in EtOH, to produce the corresponding chiral N-3-(p-tolyl) butanamides with high chemical yields and moderate diastereomeric ratios. Removal of the chiral auxiliary from N-3-(p-tolyl) butanamides gave the respective enantiomerically pure acids.

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.

One Photocatalyst, n Activation Modes Strategy for Cascade Catalysis: Emulating Coumarin Biosynthesis with (-)-Riboflavin

Generating molecular complexity using a single catalyst, where the requisite activation modes are sequentially exploited as the reaction proceeds, is an attractive guiding principle in synthesis. This requires that each substrate transposition exposes a catalyst activation mode (AM) to which all preceding or future intermediates are resistant. While this concept is exemplified by MacMillan's beautiful merger of enamine and iminium ion activation, examples in other fields of contemporary catalysis remain elusive. Herein, we extend this tactic to organic photochemistry. By harnessing the two discrete photochemical activation modes of (-)-riboflavin, it is possible to sequentially induce isomerization and cyclization by energy transfer (ET) and single-electron transfer (SET) activation pathways, respectively. This catalytic approach has been utilized to emulate the coumarin biosynthesis pathway, which features a key photochemical E → Z isomerization step. Since the ensuing SET-based cyclization eliminates the need for a prefunctionalized aryl ring, this constitutes a novel disconnection of a pharmaceutically important scaffold.

Synthesis of substituted nitroolefins: A copper catalyzed nitrodecarboxylation of unsaturated carboxylic acids

A novel, mild and convenient method for the nitrodecarboxylation of substituted cinnamic acid derivatives to their nitroolefins is achieved using a catalytic amount of CuCl (10 mol%) and tert-butyl nitrite (2 equiv.) as a nitrating agent in the presence of air. This reaction provides a useful method for the synthesis of β,β-disubstituted nitroolefin derivatives, which are generally difficult to access from other conventional methods. Additionally, this reaction is selective as the E-isomer of the acid derivatives furnishes the corresponding E-nitroolefins. One more salient feature of the method is, unlike other methods, no metal nitrates or HNO3 are employed for the transformation.

Construction of C-S bonds with a quaternary stereocenter through a formal Michael reaction: Asymmetric synthesis of tertiary thiols

Quaternary stereocenters that bear a sulfur substituent can be created with nearly perfect stereocontrol through an intramolecular Michael-type process. Lewis acids (L.A.) accelerate the intramolecular sulfur-atom transfer from the oxazolidine-2-thione functionality to the β carbon atom of the β,β-disubstituted enoyl moiety, whereas the chirality of the oxazolidine-2-thione portion controls reaction stereochemistry (see scheme).

Application of amberlite IRA-400 (basic) as a base in heck reaction

Amberlite IRA-400 (basic) has been used as a base in the Heck reaction and the generated quarternary ammonium salt might also be assisting in the reaction. The reaction is clean, simple and yields are high. The resin can be regenerated, recycled and the work-up procedure becomes simple compared to other bases used.