197963-29-4

Basic information

• Product Name: 4-Pentynal, 2,2-dimethyl-5-phenyl-
• CAS NO: 197963-29-4
• Molecular Formula: C13H14O
• Molecular Weight: 186.254
• Mol File: 197963-29-4.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 4-Pentynal, 2,2-dimethyl-5-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Pentynal, 2,2-dimethyl-5-phenyl-(197963-29-4)
• EPA Substance Registry System: 4-Pentynal, 2,2-dimethyl-5-phenyl-(197963-29-4)

Safety Data

• Hazardous Substances Data: 197963-29-4(Hazardous Substances Data)

Upstream product

• 864682-51-9 2,2-dimethyl-5-phenyl-pent-4-ynoic acid ethyl ester 
• 1794-48-5 1-bromo-3-phenylprop-2-yne 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 3355-31-5 1-chloro-3-phenyl-2-propyne 
• 78-84-2 isobutyraldehyde 

Downstream Products

• 197963-30-7 methyl N-(2,2-dimethyl-5-phenylpent-4-ynyl)glycinate 
• 1266235-16-8 2-(2-methyl-5-phenylpent-4-yn-2-yl)hexahydropyrimidine 

Relevant articles and documents

Rhodium-catalyzed arylative cyclization for the enantioselective synthesis of (trifluoromethyl)cyclobutanols

A rhodium-catalyzed cyclization of 1-(trifluoro-methyl)-4-alkyn-1-ones with arylboronic acids is described to yield a novel class of small rings: (trifluoromethyl)cyclobutanols bearing an exocyclic double bond. The use of a rhodium/chiral diene complex allowed the reaction to proceed under mild conditions, often with high enantioselectivity. An X-ray crystal structure was obtained confirming the formation of the four-membered ring products.

Synthesis of 6-(arylmethylidene)octahydropyrrolo[1,2-a]pyrimidines and 5-(arylmethylidene)hexahydropyrrolo[1,2-a]imidazoles by the interaction of alk-4-ynals with a,?-diaminoalkanes in DMSO in the presence of KOH

Cyclization of alk-4-ynals with a,?-diaminoalkanes in DMSO under the action of KOH affords bicyclic N,N-enaminals - 6-(aryl- methylidene)octahydro[1,2-a] pyrimidines and 5-(arylmethylidene)hexahydro[1,2-a]imidazoles.

Synthesis of 5-methylidenehexahydropyrrolo[l,2-a]imidazoles and 6-methylideneoctahydropyrrolo[l,2-a]pyrimidines by the reaction of 1-alkynyl-1-chlorocyclopropanes with lithium derivatives of 1,2- and 1,3-diaminoalkanes

A reaction of 1-alkynyl-1-chlorocyclopropanes with excess of lithium derivative of 1,2-diaminoethane leads to 5-methylidenehexahydropyrrolo[l,2-a] imidazoles in 35-72% yields, whereas analogous reaction with lithium derivative of 1,3-diaminopropane gives 6-methyl-ideneoctahydropyrrolo[l,2-a]pyrimidine in up to 50% yield. A mechanism of these unusual multi-step processes includes dehydrochlorination of 1-alkynyl-1-chlorocyclopropanes to form conjugated alkynylcyclopropenes capable of addition of monoalkylamide ions at the double bond, leading to the corresponding secondary cyclopropylamines; the latter under the reaction conditions isomerize to the linear imines, which further undergo a cascade cyclization with sequential involvement of the C=N and C≡C bonds.