4134-20-7

Usage

Uses

Used in Pharmaceutical Synthesis:
(2E)-2-(phenylmethylidene)hexanoic acid is used as a key intermediate in the synthesis of various pharmaceuticals. Its versatile reactivity allows for the creation of a wide range of medicinal compounds, contributing to the development of new treatments and therapies.
Used in Organic Compound Synthesis:
(2E)-2-(phenylmethylidene)hexanoic acid is also utilized in the synthesis of other organic compounds, showcasing its broad applicability in organic chemistry. Its unique structure and reactivity make it a valuable component in the creation of specialty chemicals and materials.
Used in Fragrance Ingredients:
(2E)-2-(phenylmethylidene)hexanoic acid is used as a fragrance ingredient, capitalizing on its potential to contribute to the scent profiles of various products. Its use in this industry highlights the compound's versatility beyond pharmaceutical and chemical applications.
Used in Flavor Industry:
Similarly, (2E)-2-(phenylmethylidene)hexanoic acid finds use in the flavor industry, where it can be employed to enhance or create unique taste profiles in food and beverage products. Its application in this field underscores the diverse range of industries that can benefit from its chemical properties.
Environmental Considerations:
Given the potential for bioaccumulation and environmental persistence of (2E)-2-(phenylmethylidene)hexanoic acid, it is crucial to handle and dispose of (2E)-2-(phenylmethylidene)hexanoic acid with care. Proper management practices should be implemented to minimize its impact on the environment, ensuring sustainable use in various industries.

Upstream product

• 123707-41-5 (E)-3-butyl-4-phenyl-3-buten-2-one 
• 106-70-7 methyl hexanoate 
• 100-52-7 benzaldehyde 
• 616-05-7 2-bromohexanoic acid 
• 10051-44-2 sodium caproate 
• 109-72-8 n-butyllithium 
• 637-44-5 phenylpropyolic acid 
• 204571-41-5 ethyl α,α-dibromocaproate 
• 3525-31-3 n-pentyl lithium 
• 110-43-0 n-pentyl methyl ketone 
• 124-38-9 carbon dioxide 
• 1129-65-3 (hex-1-yn-1-yl)benzene 
• 122-56-5 tributyl borane 
• 536-74-3 phenylacetylene 

Relevant academic research and scientific papers

Access to α,β-unsaturated carboxylic acids through water-soluble palladium catalyzed hydroxycarbonylation of alkynes using water as the solvent

A sulfoxantphos modified palladium-catalyzed synthesis of α,β-unsaturated carboxylic acids from alkynes with CO and H2O was described. The atom-economic hydroxycarbonylation of various symmetrical and unsymmetrical alkynes can be achieved with chemo-, stereo-, and regioselectivity, affording the corresponding carboxylic acids in good to excellent yields. Using water as the reaction solvent, the water-soluble palladium catalyst was easily separated from the product and could be reused for 5 cycles.

Palladium-Catalyzed Highly Regioselective Hydrocarboxylation of Alkynes with Carbon Dioxide

A Pd-catalyzed highly regioselective hydrocarboxylation of alkynes with carbon dioxide has been established. By the combination of Pd(PPh3)4 and 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (binap), a variety of functionalized alkynes, including aryl alkynes, aliphatic alkynes, propargylamines, and propargyl ethers, could be leveraged to provide a wide array of α-acrylic acids in high yields with high regioselectivity under mild reaction conditions. Experimental and DFT mechanistic studies revealed that this reaction proceeded via the cyclopalladation process of alkynes and carbon dioxide in the presence of binap to generate a five-membered palladalactone intermediate and enabled the formation of Markovnikov adducts. Moreover, this strategy provided an effective method for the late-stage functionalization of alkyne-containing complicated molecules, including natural products and pharmaceuticals.

Copper-Catalyzed Stereodefined Construction of Acrylic Acid Derivatives from Terminal Alkynes via CO2 Insertion

IPrCuCl catalyzes the CO2 insertion reaction undergone by a dialkylvinylborane intermediate derived from alkynyltrialkylborate by a 1,2-alkyl group migration to afford α-alkyl acrylic acids with excellent regio- and stereoselectivities.

The Development of a Stereoselective Method for the Synthesis of Tetrasubstituted Derivatives of α,β-Unsaturated Carboxylic Acids

Alkenes possessing four different carbon-linked substituents are the main structural motif of many biologically active compounds. The derivatives of (2E)-3-(3-methoxyphenyl)-2-methylpent-2-enoic acid ((E)-2c) are suitable precursors for the synthesis of Tapentadol, a novel centrally acting analgesic. It was found that the Ni-carbometallation reaction of disubstituted alkyne 8 with CO2and an Et2Zn allows for efficient and practical preparation of (E)-2c as a single (E)-regioisomer in 89% of isolated yield. The influence of the size of the aliphatic substituent of alkyne and the steric hindrance of the organozinc reagent on stereochemical course of the carbometallation reaction was evaluated. Finally, air-stable Ni(dme)Cl2was proposed as an alternative to widely used Ni(cod)2catalyst.

Copper-catalyzed hydrocarboxylation of alkynes using carbon dioxide and hydrosilanes

Getting a fix: The copper-catalyzed hydrocarboxylation of alkynes using carbon dioxide in the presence of a hydrosilane, which serves as a reducing agent, has been developed (see scheme). Copper fluorides bearing N-heterocyclic carbene ligands such as IMes and Cl2IPr show high catalytic activities.

Highly E-selective synthesis of α,β-unsaturated amides from N-2- methoxyphenyl aldimines via lithium ynolates

Lithium ynolates reacted with N-2-methoxyphenyl (OMP) aldimines to afford α,β-unsaturated amides in excellent E-selectivity via a retro- Mannich reaction of the 2:1 adducts (β-lactams), followed by cleavage of the β-lactam enolates. (C) 2000 Elsevier Science Ltd.

Reactions d'addition conjuguee d'organolithiens aux acides carboxyliques α, β-insatures

In THF at -78 deg C, organolithium derivatives and unprotected α,β-unsaturated carboxylic acids give a conjugated addition reaction. Reactions of 1- and 2-napthoic acids with various organolithium derivatives and electrophiles are reported. Two X-ray studies show that the reaction occurs with a good diastereoselectivity: the dilithiated enolate formed as an intermediate adds the electrophile exclusively via the face opposite to that of the organolithium. A study of the 1H NMR spectra of the products obtained shows that these compounds adopt a preffered conformation in solution. The protonolysis of the intermediate enolate by trifluoroacetic acid in an inverted mode gives rise to the formation of 1,2-disubstituted dihydronapthalenes. With acyclic α,β-unsaturated carboxylic acids, the diastereoselectivity of the reaction is marginal. With secondary butyllithium, the protonolysis of the intermediate enolates gives a 1,4-addition and an average diastereoselectivity. Reaction of phenylpropiolic acid with butyllithium gives rise to the formation of a produst resulting from a trans addition to the triple bond; the organolithium derivative adds in α to the carboxylic group. - Key words: 1,4-addition reactions; carboxylic acids; organolithium derivatives.

A highly stereoselective synthesis of tri- and tetrasubstituted olefins via ynolates

A highly stereoselective synthesis of tri- and tetrasubstituted olefins has been accomplished by the reactions of ynolates with aldehydes and ketones.

α-LITHIOALKYLPHOSPHONATES AS FUNCTIONAL GROUP CARRIERS. PART II. A DIRECT (E)-CINNAMIC AND 2-ALKYL-CINNAMIC ACIDS SYNTHESIS.

Sequential treatment of α-lithioalkylphosphonates with tert-butyl fluoroformate or di-tert-butyl dicarbonate and an aromatic aldehyde gives tert-butyl acrylic esters convertible into acrylic acids by protolysis with trifluoroacetic acid.

Contrasting behaviour of (E)-3-(trimethylsilyl)- and (E)-3-phenylpropenoic acids towards n-butyl- and tert-butyllithium

The title compounds 2 and 9 react with tert-buthyllithium to give considerable amounts of 'anti-Michael' adducts 3 and 10, respectively, in which the tert-butyl group is bonded to C-2.A single-electron-transfer (SET) mechanism is proposed for these reacti