127404-74-4

Basic information

• Product Name: (E)-4-(4-tolyl)-3-butenoic acid
• Synonyms: (E)-4-(4-tolyl)-3-butenoic acid
• CAS NO: 127404-74-4
• Molecular Weight: 176.215
• Mol File: 127404-74-4.mol

Chemical Properties

• CAS DataBase Reference: (E)-4-(4-tolyl)-3-butenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4-(4-tolyl)-3-butenoic acid(127404-74-4)
• EPA Substance Registry System: (E)-4-(4-tolyl)-3-butenoic acid(127404-74-4)

Safety Data

• Hazardous Substances Data: 127404-74-4(Hazardous Substances Data)

Upstream product

• 141-82-2 malonic acid 
• 104-09-6 4-methylphenylacetaldehyde 
• 98-59-9 p-toluenesulfonyl chloride 
• 625-38-7 but-3-enoic acid 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 64-18-6 formic acid 
• 122058-30-4 4-methylcinnamyl alcohol 
• 58824-48-9 1-(4-methylphenyl)-2-propen-1-ol 
• 104-87-0 4-methyl-benzaldehyde 
• 51114-94-4 (2-carboxyethyl)triphenylphosphonium bromide 
• 106-38-7 para-bromotoluene 
• 36626-29-6 (2-carboxyethyl)triphenylphosphonium chloride 

Downstream Products

• 1613157-22-4 tert-butyl (E)-4-(p-tolyl)but-3-enoate 
• 20840-08-8 (E)-4-(4-methylphenyl)but-3-en-1-ol 
• 46413-67-6 5-(4-methylphenyl)-1H-pyrazole-3-carboxylic acid 
• 192701-73-8 methyl 5-(p-tolyl)-1H-pyrazole-3-carboxylate 
• 1589523-24-9 methyl (E)-2-diazo-4-(p-tolyl)but-3-enoate 
• 1250907-64-2 methyl (E)-4-(p-tolyl)but-3-enoate 

Relevant articles and documents

Alkene Dioxygenation with Malonoyl Peroxides: Synthesis of γ-Lactones, Isobenzofuranones, and Tetrahydrofurans

Treatment of homoallylic alcohols or carboxylic acids with malonoyl peroxide 1 provides a stereoselective method for the preparation of tetrahydrofurans, γ-lactones, and isobenzofuranones in 44-82% yield and up to 27:1 trans selectivity. Application of this simple and effective heterocyclization in the synthesis of the antidepressant citalopram is also described.

A novel phenylsulfenylation of unsaturated acids or alcohols by methyl phenyl sulfoxide and substoichiometric (COCl)2

Phenylsulfenylation of unsaturated acids and alcohols has been achieved by methyl phenyl sulfoxide (PhSOCH3) and substoichiometric (COCl)2 in CH3CN. The corresponding cyclization products, lactones with a phenylthio group from unsaturated acids were obtained in mediate to good yields, whereas the cyclic ethers with a phenylthio group from unsaturated alcohols in relatively low yields. PhSOH was proposed to be the key active species for phenylsulfenylation, which was generated in situ by the reaction of PhSOCH3 with substiochiometric amount of (COCl)2. Anhydrous HCl could replace (COCl)2 in the reactions to give the comparable results.

Palladium-Catalyzed Direct C-H Arylation of 3-Butenoic Acid Derivatives

We report herein a direct method to synthesize 4-aryl-3-butenoic acid through a carboxylic-acid-directed oxidative Heck reaction. The various 4-aryl-3-butenoic acids are easily prepared in moderate to good yields. In view of the promising bioactivity of 4-phenyl-3-butenoic acid previously reported, its derivatives reported here may be bioactive.

Enantioselective Synthesis of γ-Lactams by Lewis Base Catalyzed Sulfenoamidation of Alkenes

A method for the catalytic, enantioselective, intramolecular 1,2-sulfenoamidation of alkenes is described. Lewis base activation of a suitable sulfur electrophile generates an enantioenriched, thiiranium ion intermediate from a β,γ-unsaturated sulfonyl ca

Intramolecular Cyclization of Vinyldiazoacetates as a Versatile Route to Substituted Pyrazoles

Vinyldiazo compounds undergo a thermal electrocyclization to form pyrazoles in yields of up to 95percent. The reactions are operationally simple, use readily available starting materials, require no intervention of a catalyst, and enable the synthesis of mono-, di- A nd tri-substituted pyrazoles. With the ability to produce highly substituted pyrazoles and the flexibility in installing various types of substituents, this method constitutes a new entry to this valuable heterocyclic scaffold and may be of interest to all branches of the chemical industry.

An Enzymatic Platform for the Highly Enantioselective and Stereodivergent Construction of Cyclopropyl-δ-lactones

Abiological enzymes offers new opportunities for sustainable chemistry. Herein, we report the development of biological catalysts derived from sperm whale myoglobin that exploit a carbene transfer mechanism for the asymmetric synthesis of cyclopropane-fused-δ-lactones, which are key structural motifs found in many biologically active natural products. While hemin, wild-type myoglobin, and other hemoproteins are unable to catalyze this reaction, the myoglobin scaffold could be remodeled by protein engineering to permit the intramolecular cyclopropanation of a broad spectrum of homoallylic diazoacetate substrates in high yields and with up to 99 % enantiomeric excess. Via an alternate evolutionary trajectory, a stereodivergent biocatalyst was also obtained for affording mirror-image forms of the desired bicyclic products. In combination with whole-cell transformations, the myoglobin-based biocatalyst was used for the asymmetric construction of a cyclopropyl-δ-lactone scaffold at a gram scale, which could be further elaborated to furnish a variety of enantiopure trisubstituted cyclopropanes.

Direct Enantioselective and Regioselective Alkylation of β,γ-Unsaturated Carboxylic Acids with Chiral Lithium Amides as Traceless Auxiliaries

Efficient asymmetric alkylation of β,γ-unsaturated carboxylic acids without prior functionalization is enabled by chiral lithium amides. Enantioselectivity is imparted by a putative mixed lithium amide-enediolate aggregate that acts a traceless auxiliary formed in situ, allowing for a direct asymmetric alkylation and a simple recovery of the chiral reagent.

Direct palladium-catalyzed carbonylative transformation of allylic alcohols and related derivatives

A direct, palladium-catalyzed, carbonylative transformation of allylic alcohols for the synthesis of β,γ-unsaturated carboxylic acids has been developed. With formic acid as the CO source, various allylic alcohols were conveniently transformed into the corresponding β,γ-unsaturated carboxylic acids with excellent linear and (E)-selectivity. The reaction was performed under mild conditions; toxic CO gas manipulation and high-pressure equipment were avoided in this procedure.

Efficient Pd-Catalyzed Regio- and Stereoselective Carboxylation of Allylic Alcohols with Formic Acid

Formic acid is efficiently used as a C1 source to directly carboxylate allylic alcohols in the presence of a low loading of palladium catalyst and acetic anhydride as additive to afford β,γ-unsaturated carboxylic acids with excellent chemo-, regio-, and stereoselectivity. The reaction proceeds through a carbonylation process with in situ-generated carbon monoxide under mild conditions, avoiding the use of high-pressure gaseous CO. A bisphosphine ligand with a large bite angle (4,5-bis{diphenylphosphino}-9,9-dimethylxanthene, Xantphos) was found to be uniquely effective for this transformation. The regio- and stereoconvergence of this reaction is ascribed to the thermodynamically favored isomerization of the allylic electrophile in the presence of the palladium catalyst.

Catalytic asymmetric aminolactonization of 1,2-disubstituted alkenoic acid esters: Efficient construction of aminolactones with an all-carbon quaternary stereo-centre

Chiral BOX-Cu(OTf)2 catalyzed enantioselective aminolactonization of the tert-butyl ester of alkenoic acids has been developed via in situ aziridination using PhINNs as the nitrene source. It provides exclusively trans-γ- and δ-amino lactones including an additional all-carbon quaternary stereo-centre with up to 98% ee in good to excellent yields. the Partner Organisations 2014.