21100-66-3

Basic information

• Product Name: 4,4,4-trichloro-1-phenyl-but-2-en-1-one
• Synonyms: 4,4,4-trichloro-1-phenyl-but-2-en-1-one
• CAS NO: 21100-66-3
• Molecular Weight: 249.524
• Mol File: 21100-66-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4,4,4-trichloro-1-phenyl-but-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4,4-trichloro-1-phenyl-but-2-en-1-one(21100-66-3)
• EPA Substance Registry System: 4,4,4-trichloro-1-phenyl-but-2-en-1-one(21100-66-3)

Safety Data

• Hazardous Substances Data: 21100-66-3(Hazardous Substances Data)

Upstream product

• 768-03-6 Phenyl vinyl ketone 
• 98-86-2 acetophenone 
• 13505-41-4 4,4,4-trichloro-3-hydroxy-1-phenylbutan-1-one 
• 7664-93-9 sulfuric acid 
• 64-17-5 ethanol 

Downstream Products

• 40646-34-2 4,4,4-trichloro-1,3-diphenyl-butan-1-one 
• 22175-78-6 3-phenyl-6H-1,2-oxazin-6-one 
• 73498-36-9 3-Phenyl-5-trichlormethyl-Δ²-isoxazolin 
• 1184912-96-6 5-dichloromethyl-3-phenyl-2-pyrazoline 
• 807331-42-6 4,4-dichloro-1-phenylbut-3-en-1-one 
• 1184913-18-5 1-methyl-3-phenyl-5-trichloromethyl-2-pyrazoline 
• 1318796-27-8 C₁₇H₁₅Cl₃N₂O₂ 
• 1298064-82-0 C₁₆H₁₂Cl₃N₃O 
• 1316227-82-3 4,4,4-trichloro-3-(7-methyl-1H-indol-3-yl)-1-phenylbutan-1-one 

Relevant articles and documents

Changing stereoselectivity and regioselectivity in copper(i)-catalyzed 5-: Exo cyclization by chelation and rigidity in aminoalkyl radicals: Synthesis towards diverse bioactive N-heterocycles

The work reveals that a chelate-Type interaction in the transition state of a β-Aminoalkyl radical in a copper(i)-catalyzed 5-exo-Trig radical cyclization step changes the usual stereochemistry of the NH-pyrrolidine ring predicted by the Beckwith-Houk transition state model. In contrast, the rigidity in the fused β-Aminoalkyl radical changes the Baldwin's predicted 5-exo to 6-endo cyclization mode, preferentially forming a piperidine ring over a pyrrolidine ring via a geometrically constrained transition state. The resultant diverse NH-pyrrolidines, pyrrolines and piperidines are sources of the bioactive natural product roseophilin and the drug Ritalin among others.