186602-93-7

Usage

Physical Form

White to light yellow crystalline powder

Solubility

Soluble in organic solvents like ethanol and ether

Applications

Intermediate in pharmaceutical synthesis
Intermediate in agrochemical synthesis
Intermediate in organic compound synthesis
Used in dye and pigment production

Biological/Pharmacological Studies

Investigated for potential biological and pharmacological activities

Versatile Use

Finds applications across various industries and research fields.

Upstream product

• 109134-07-8 t-butyl<3-(trifluoromethyl)phenyl>-carbamate 
• 68-12-2 N,N-dimethyl-formamide 
• 109466-87-7 4-(trifluoromethyl)-2-nitrobenzaldehyde 
• 402-13-1 2-amino-4-trifluoromethylbenzoic acid 
• 98-16-8 3-trifluoromethylaniline 
• 320-94-5 2-nitro-4-trifluoromethylbenzoic acid 
• 133605-27-3 (2-nitro-4-(trifluoromethyl)phenyl)methanol 

Downstream Products

• 1396548-59-6 N-(2-formyl-5-(trifluoromethyl)phenyl)-4-methylbenzenesulfonamide 
• 450-62-4 7-(trifluoromethyl)-1,2,3,4-tetrahydroquinoline 
• 109133-94-0 tert-butyl N-(2-formyl-5-trifluoromethyl-phenyl)carbamate 

Relevant academic research and scientific papers

Visible-light-induced radical isocyanide insertion protocol for the synthesis of difluoromethylated spiro[indole-3,3′-quinoline] derivatives

Herein, we report the first protocol for visible-light-induced radical isocyanide insertion reactions between 3-(2-isocyanobenzyl)-indoles and bromodifluoroacetates or bromodifluoroacetamides. The protocol, which has good functional group tolerance and a broad substrate scope, constitutes an efficient and general route to difluoromethylated spiro[indole-3,3′-quinoline] derivatives. This journal is

Highly Diastereoselective Synthesis of Trifluoromethyl Indolines by Interceptive Benzylic Decarboxylative Cycloaddition of Nonvinyl, Trifluoromethyl Benzoxazinanones with Sulfur Ylides under Palladium Catalysis

A highly diastereoselective synthesis of trifluoromethyl-substituted indolines under palladium catalysis is disclosed. The reaction proceeds by interceptive decarboxylative benzylic cycloaddition (IDBC) of nonvinyl, trifluoromethyl benzoxazinanones with sulfur ylides. The palladium-π-benzyl zwitterionic intermediates are suggested for this transformation, and this would be the first example of an IDBC reaction.

Pd-Catalyzed Three-Component Domino Reaction of Vinyl Benzoxazinanones for Regioselective and Stereoselective Synthesis of Allylic Sulfone-Containing Amino Acid Derivatives

A Pd-catalyzed, highly regioselective and stereoselective three-component domino allylic substitution/N-H carbene insertion reaction under mild conditions is described. This reaction demonstrates a wide substrate scope and satisfactory functional group tolerance, providing a broad range of allylic sulfone-containing amino acid derivatives. Moreover, DBU mediates highly diastereoselective cross-dehydrogenative coupling annulation of allylic sulfones without using peroxides or any metal oxidants. This developed protocol affords 7-membered ring heterocyclic compounds incorporating both sulfone-containing amino acid esters and one quaternary carbon center. Mechanistic studies indicate that an unusual umpolung of glycine occurred in this annulation.

Synthesis of quinolines and naphthyridines: Via catalytic retro-aldol reaction of β-hydroxyketones with ortho -aminobenzaldehydes or nicotinaldehydes

A Cu(i)-catalyzed retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes and nicotinaldehydes is reported that produces a range of quinolines and naphthyridines with high efficiency and selectivity. This reaction uses β-hydroxyketones as a regiospecific ketone-protected enolate source via copper-catalyzed retro-aldol Cα-Cβ bond cleavage. The in situ generated copper enolate undergoes kinetically favorable cyclization with ortho-amino aryl aldehydes to produce quinolines and naphthyridines in a chemo- and regioselective manner. The mild and weakly basic reaction conditions also suppress possible side reactions of benzaldehydes under strongly basic conditions, resulting in improved reaction yields.

Decarboxylative [4+2] Cycloaddition by Synergistic Palladium and Organocatalysis

A novel reaction based on synergistic catalysis, combining palladium- and organocatalysis has been developed. The palladium catalyst activates vinyl benzoxazinanones via a decarboxylation to undergo a [4+2] cycloaddition with iminium-ion activated α,β-uns

Cycloadditions with Bromo-Substituted Morita-Baylis-Hillman Adducts of Isatins and N-(ortho-Chloromethyl)aryl Amides

Efficient construction of a challenging aza-spirocycloheptane oxindole scaffold is reported through an unprecedented [4 + 3] cycloaddition reaction with bromo-substituted Morita-Baylis-Hillman adducts of isatins and N-(ortho-chloromethyl)aryl amides. Both reactive intermediates, the allylic phosphonium ylides and aza-o-quinone methides, were in situ generated, chemoselectively facilitated by a Lewis base and Bronsted base, respectively.

N-Heterocyclic Carbene-Catalyzed Synthesis of 2-Aryl Indoles

Transition metal-free catalytic methods for access to 2-arylindole compounds.

Synthesis of polysubstituted cyclopenta[b]indoles via relay gold(i)/Bronsted acid catalysis

An efficient relay catalytic process involving Au(i)/Bronsted acid to access various polysubstituted cyclopentannulated indoles from easily accessible 1-(2-aminophenyl)prop-2-ynols and readily available 1,3-dicarbonyls has been developed. In an unprecedented event, the intermediate 2-indolylmethyl cations undergo the cation-Ene reaction with various 1,3-dicarbonyls followed by an intramolecular Friedel-Crafts-type reaction generating functionalized cyclopenta[b]indoles. This journal is

N-heterocyclic-carbene-catalyzed synthesis of 2-aryl indoles

A convergent and efficient transition-metal-free catalytic synthesis of 2-aryl-indoles has been developed. The interception of a highly reactive and transient aza-ortho-quinone methide by an acyl anion equivalent generated through N-hetereocyclic carbene catalysis is central to this successful strategy. High yields and a wide scope as well as the streamlined synthesis of a kinase inhibitor are reported. Umpolung: N-heterocyclic carbene catalysis is used for the convergent and efficient transition-metal-free synthesis of 2-aryl-indoles. The interception of a highly reactive and transient aza-ortho-quinone methide by an acyl anion equivalent is central to this successful strategy. The reaction exhibits high yields and a wide scope, and it has been applied to a streamlined synthesis of a kinase inhibitor.

Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands

We have reported previously the novel δ opioid agonist KNT-127 which showed high affinity and selectivity for the δ receptor. Moreover, the analgesic effect of subcutaneously administered KNT-127 was more potent than that of a prototypical δ agonist (-)-TAN-67 in the acetic acid writhing test. This study of the structure-activity relationship of KNT-127 derivatives focused on the introduction of substituents onto the 5′-, 6′-, 7′- or 8′-position of the quinoline ring and revealed that many derivatives with 5′- or 8′-substituents showed high affinities and selectivities for the δ receptor. Especially, SYK-153 with an 8′-OH group showed the highest affinity and the most balanced and highest selectivity for the δ receptor among the synthesized compounds.