1574469-96-7

Basic information

• Product Name: (Z)-3-[(2-aminophenyl)amino]-4-(4-(tert-butyl)phenyl)-1-(4-chlorophenyl)but-2-en-1-one
• Synonyms: (Z)-3-[(2-aminophenyl)amino]-4-(4-(tert-butyl)phenyl)-1-(4-chlorophenyl)but-2-en-1-one
• CAS NO: 1574469-96-7
• Molecular Weight: 418.966
• Mol File: 1574469-96-7.mol

Chemical Properties

• CAS DataBase Reference: (Z)-3-[(2-aminophenyl)amino]-4-(4-(tert-butyl)phenyl)-1-(4-chlorophenyl)but-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-3-[(2-aminophenyl)amino]-4-(4-(tert-butyl)phenyl)-1-(4-chlorophenyl)but-2-en-1-one(1574469-96-7)
• EPA Substance Registry System: (Z)-3-[(2-aminophenyl)amino]-4-(4-(tert-butyl)phenyl)-1-(4-chlorophenyl)but-2-en-1-one(1574469-96-7)

Safety Data

• Hazardous Substances Data: 1574469-96-7(Hazardous Substances Data)

Upstream product

• 852211-48-4 1-(4-chlorophenyl)-4-(4-tert-butylphenyl)but-3-yn-1-one 
• 95-54-5 1,2-diamino-benzene 

Relevant articles and documents

Regioselective “hydroamination” of alk-3-ynones with non-symmetrical o-phenylenediamines. Synthesis of diversely substituted 3H-1,5-benzodiazepines via (Z)-3-amino-2-alkenones

The reaction of alk-3-yn-1-ones (a bifunctional reagent) with o-phenylenediamines provides an effective synthetic method with high atom economy for the preparation of diversely substituted 1,5-3H-benzodiazepines. The reaction initially leads to the formation of conjugated enaminones (3-amino-2-alkenones, 51-99%), at room temperature, which constitutes a formal non-catalyzed hydroamination of the non-conjugated alkyne. Non-symmetrical o-phenylenediamines react in a regioselective fashion with respect to amino groups. Both the direct microwave-accelerated reaction of o-phenylenediamines with alkynones in ethanol and the intramolecular cyclization of intermediate enaminones in ethanol/acetic acid lead to substituted 1,5-benzodiazepines with good yields (39-92 and 26-99%). The regio- and stereochemical outcomes of these processes are confirmed by the X-ray structure determination of (Z)-3-[(2-amino-4-methylanilino)-4-(4-methylphenyl)-1-phenylbut-2-en-1-one], 4-[(4-methylphenyl)methyl]-7-nitro-2-phenyl-3H-1,5-benzodiazepine and 6,8-dimethyl-4-(4-methylbenzyl)-2-phenyl-3H-benzo[b][1,5]diazepine.

Catalyst-free chemo-/regio-/stereo-selective amination of alk-3-ynones. Synthesis of 1,5-benzodiazepines and 3-amino-2-alkenones

Reaction of alk-3-yn-1-ones with o-phenylenediamines provides an effective method with high atom economy for the synthesis of diversely substituted benzodiazepines and conjugated enaminones. This microwave-accelerated reaction proceeds in ethanol in the absence of a catalyst and leads to benzyl-substituted 1,5-benzodiazepines with good yields (70-92%). A room temperature protocol with the same set of reagents (stabilized with triethylamine) leads to enaminones (3-amino-2-alkenones, 70-99%). The tautomer formed and the regio- and stereochemistry of the process are confirmed by the X-ray crystallographic structure determination of 2-(4-methylbenzyl)-4-phenyl-3H-benzo[b][1,5]diazepine and (Z)-3-[(2-amino-4,5-dimethylphenyl)amino]-4-(4-tert-butylphenyl)-1-(4- chlorophenyl)but-2-en-1-one.