80992-93-4

Usage

Uses

Used in Pharmaceutical Industry:
1-[4-(TRIFLUOROMETHYL)PHENYL]BUT-1-EN-3-ONE is used as a synthetic intermediate for the development of new drugs. Its trifluoromethyl group contributes to the modification of the physicochemical properties and pharmacokinetic behavior of the resulting molecules, which is crucial for enhancing drug efficacy and safety.
Used in Agrochemical Industry:
In the agrochemical sector, 1-[4-(TRIFLUOROMETHYL)PHENYL]BUT-1-EN-3-ONE serves as a key building block for the synthesis of various agrochemicals. Its ability to alter the properties of the molecules it is part of makes it instrumental in creating effective and targeted agrochemicals for crop protection and other agricultural applications.
The diverse synthetic applications of 1-[4-(TRIFLUOROMETHYL)PHENYL]BUT-1-EN-3-ONE underscore its importance in the advancement of both pharmaceutical and agrochemical research and development.

InChI:InChI=1/C11H9F3O/c1-8(15)2-3-9-4-6-10(7-5-9)11(12,13)14/h2-7H,1H3/b3-2+

Upstream product

• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 67-64-1 acetone 
• 78-94-4 methyl vinyl ketone 
• 455-14-1 4-trifluoromethylphenylamine 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 123-42-2 4-Hydroxy-4-methyl-2-pentanone 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 113170-92-6 1-(but-3-en-1-yl)-4-(trifluoromethyl)benzene 
• 1360611-42-2 1-(4-(trifluoromethyl)phenyl)but-2-yn-1-ol 

Downstream Products

• 1420293-50-0 4-((4-chlorophenyl)thio)-4-(4-(trifluoromethyl)phenyl)butan-2-one 
• 113947-86-7 1-methyl-4-(p-trifluoromethyl)phenyl-1-butene 
• 1418030-39-3 4-methyl-2,6-diphenyl-10-[4-(trifluoromethyl)phenyl]-2,3-diazaspiro[4.5]dec-3-ene-1,8-dione 
• 1338577-24-4 3-O-[(E)-2-oxo-4-(4-(trifluoromethyl)phenyl)but-3-en-1-yl]kaempferol 
• 57132-19-1 4-(4-(trifluoromethyl)phenyl)butan-2-one 
• 1199945-10-2 (E)-(1-(p-trifluoromethyl)phenyl)-3-methyl-1,5-hexadien-3-ol 
• 80092-72-4 (2R,3S)-7-Chloro-1-[(E)-3-dimethylamino-propylimino]-2-methyl-3-(4-trifluoromethyl-phenyl)-1,3,4,10-tetrahydro-2H-acridin-9-one 

Relevant academic research and scientific papers

Polysubstituted Indole Synthesis via Palladium/Norbornene Cooperative Catalysis of Oxime Esters

Polysubstituted indoles are prevalent in pharmaceuticals, agrochemicals, and organic materials. Presented herein is the fact that polyfunctionalized indoles can be efficiently constructed from easily accessible oxime esters and aryl iodides, involving a palladium/norbornene synergistic synthesis. The reaction is enabled by a unique class of electrophiles in palladium/norbornene cooperative catalysis, which are oxime esters derived from simple ketone. The broad substrate scope and high functional group tolerance could make this method attractive for the synthesis of polysubstituted indoles.

Selective Cross-Dehydrogenative C(sp3)-H Arylation with Arenes

Selective C(sp3)-C(sp2) bond construction is of central interest in chemical synthesis. Despite the success of classic cross-coupling reactions, the cross-dehydrogenative coupling between inert C(sp3)-H and C(sp2)-H bonds represents an attractive alternative toward new C(sp3)-C(sp2) bonds. Herein, we establish a selective inter-and intramolecular C(sp3)-H arylation of alcohols with nondirected arenes that thereby provides a general pathway to access a wide range of β-arylated alcohols, including tetrahydronaphthalen-2-ols and benzopyran-3-ols, with high to excellent chemo-and regioselectivity.

RhIII-Catalyzed Synthesis of Highly Substituted 2-Pyridones using Fluorinated Diazomalonate

A RhIII-catalyzed strategy was developed for the rapid construction of highly substituted 2-pyridone scaffolds using α,β-unsaturated oximes and fluorinated diazomalonate. The reaction proceeds through direct, site-selective alkylation based on migratory insertion and subsequent cyclocondensation. A wide substrate scope with different functional groups was explored. The requirement of fluorinated diazomalonate was explored for this transformation. The developed methodology was further extended with the synthesis of the bioactive compound.

Silica gel-mediated self-aldol reactions of highly volatile aldehydes under organic solvent-free conditions without reflux condenser

Silica gel-mediated self-aldol reactions were catalyzed by piperidine to give the corresponding α,β-conjugated aldehydes in good yields. The aldol reactions of 4-nitro-, 4-trifluoromethyl-, and 4-chlorobenzaldehydes with acetone afforded the corresponding aldol products. Highly volatile aldehydes and acetone could be employed even without a reflux condenser for these reactions. Silica gel could be recycled five times without any significant decrease of the yields of the products.

Discovery of novel 5-methyl-1H-pyrazole derivatives as potential antiprostate cancer agents: Design, synthesis, molecular modeling, and biological evaluation

Androgen receptor (AR) signaling functions as a core driving force for the progression of prostate cancer (PCa), and AR has been proved to be an effective therapeutic target even for castration-resistant prostate cancer (CRPC). Herein, structural modification via a fragments splicing strategy was performed based on two lead compounds T3 and 10e, leading to the discovery of a series of 5-methyl-1H-pyrazole derivatives. AR reporter gene assay revealed compounds A13 and A14 as potent AR antagonists. Some of the compounds in this series inhibited growth of PCa LNCaP cells more efficiently than enzalutamide. A13 and A14 also showed improved metabolic stability compared with 10e in human liver microsomes.

Rh(III)-Catalyzed Enaminone-Directed Alkenyl C-H Activation for the Synthesis of Salicylaldehydes

A Rh(III)-catalyzed enaminone-directed alkenyl C-H coupling with alkynes for the synthesis of salicylaldehyde derivatives is reported. This represents a unique example of benzene ring framework formation through a transition-metal-catalyzed, directed C-H activation strategy. The two incorporated reactive functionalities, aldehyde and hydroxy groups, provide convenient synthetic handles for further structural elaboration.

Gram-scale preparation of dialkylideneacetones through Ca(OH)2-catalyzed Claisen-Schmidt condensation in dilute aqueous EtOH

A synthetic method of dialkylideneacetones has been developed. Compared with known protocols, the method employed catalytic Ca(OH)2 as the cheap, mild base catalyst and dilute aqueous EtOH (20%, v/v) as the green and safe solvent. The procedure was easily operated: In most cases, the product could be isolated by a simple filtration, and purified by washing with water. This paper provided experimental details of the reactions, which could be applied in gram-scale synthesis and should be a very reliable and practical protocol to prepare these useful compounds in laboratory and at the industrial level.

Diastereoselective synthesis of β-amino ketone and acid derivatives by palladium-catalyzed conjugate addition

The first diastereoselective synthesis of β-amino ketone and β-amino acid derivatives by palladium-catalyzed conjugate addition of arylboronic acids to chiral β-enamino ketones and β-enamino esters is reported. The catalytic system employing (S)-4-(tert-butyl)oxazolidin-2-one as the chiral auxiliary in water under an air atmosphere provides β-amino ketone and β-amino acid derivatives in high yields with excellent diastereoselectivity.

A method of preparing alpha,beta-unsaturated ketones

The invention relates to a method of preparing alpha,beta-unsaturated ketones. The method is characterized by comprising steps of (1) adding a copper catalyst and an alkali into a reaction tube, adding a liquid mixture of a solvent and reactants which are a beta-hydroxy ketone and an aromatic aldehyde under nitrogen protection into the reaction tube and reacting the mixture; (2) performing filtration, extraction, drying, and low-pressure solvent removing after the reaction is finished to obtain an alpha,beta-unsaturated ketone crude product; and (3) performing separation and purification to obtain an alpha,beta-unsaturated ketone product. A copper enolate is generated in situ through a retrograde aldol condensation reaction and is further subjected to aldol condensation with the aromatic aldehyde to obtain the final product. The beta-hydroxy ketone and the aromatic aldehyde are injected through injectors under nitrogen protection, and the reaction is performed under stirring in an oil bath pot having a temperature of 25-120 DEG C for 3-8 h. The method has characteristics of mild conditions, simple operation, easily available raw materials, and environment protection and is hopped to be widely applied in the fine chemical synthesis fields such as medicine intermediates, perfume and pesticides.

Discovery of New Monocarbonyl Ligustrazine-Curcumin Hybrids for Intervention of Drug-Sensitive and Drug-Resistant Lung Cancer

The elevation of oxidative stress preferentially in cancer cells by inhibiting thioredoxin reductase (TrxR) and/or enhancing reactive oxygen species (ROS) production has emerged as an effective strategy for selectively targeting cancer cells. In this study, we designed and synthesized 21 ligustrazine-curcumin hybrids (10a-u). Biological evaluation indicated that the most active compound 10d significantly inhibited the proliferation of drug-sensitive (A549, SPC-A-1, LTEP-G-2) and drug-resistant (A549/DDP) lung cancer cells but had little effect on nontumor lung epithelial-like cells (HBE). Furthermore, 10d suppressed the TrxR/Trx system and promoted intracellular ROS accumulation and cancer cell apoptosis. Additionally, 10d inhibited the NF-κB, AKT, and ERK signaling, P-gp-mediated efflux of rhodamine 123, P-gp ATPase activity, and P-gp expression in A549/DDP cells. Finally, 10d repressed the growth of implanted human drug-resistant lung cancer in mice. Together, 10d acts a novel TrxR inhibitor and may be a promising candidate for intervention of lung cancer.