68109-75-1

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
1-Cyclohexyl-2,5-dihydro-1H-pyrrole serves as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides.
Used in Fragrance Industry:
As a fragrance ingredient, 1-Cyclohexyl-2,5-dihydro-1H-pyrrole is used in perfumes and personal care products to create unique and complex scents, enhancing the sensory experience of these products.
Used in Materials Science:
1-Cyclohexyl-2,5-dihydro-1H-pyrrole has potential applications in the field of materials science, where it may contribute to the development of novel materials with specific properties.
Used in Organic Synthesis:
1-Cyclohexyl-2,5-dihydro-1H-pyrrole is also utilized in organic synthesis, where it can act as a building block for the creation of more complex organic molecules, expanding the scope of chemical research and development.

InChI:InChI=1/C10H17N/c1-2-6-10(7-3-1)11-8-4-5-9-11/h4-5,10H,1-3,6-9H2

Upstream product

• 54391-01-4 N,N-di-2-propenylcyclohexylamine 
• 108-91-8 cyclohexylamine 
• 50-00-0 formaldehyd 
• 18292-76-7 N-(prop-2-yn-1-yl)cyclohexanamine 
• 1953-56-6 (Z)-but-2-ene-1,4-diyl dimethanesulfonate 

Downstream Products

• 31708-14-2 1-cyclohexyl-1H-pyrrole 

Relevant academic research and scientific papers

An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis

The synthesis of N-aryl, N-tosyl, and N-alkyl pyrrolines from allyl alcohols and amines has been developed. The reaction sequence includes a palladium-catalyzed allylation step in which non-manipulated allyl alcohol is used to generate the diallylated amine in good to excellent yield. An excess of allyl alcohol was necessary for efficient diallylation of the amine, where the excess alcohol could be recycled three times. For aryl and tosyl amines, Pd[P(OPh)3]4 was used and for benzyl and alkyl amines a catalytic system comprising Pd(OAc)2, PnBu3, and BEt3 was used. Both the electronic properties and the steric influence of the amine affected the efficiency of the allylation. The isolated diallylated amines were transformed into their corresponding pyrrolines by ring-closing metathesis catalyzed by (H2IMes)(PCy3)Cl 2RuCHPh in good to excellent yield. A one-pot reaction was developed in which aniline was transformed into the corresponding pyrroline without isolating the diallylated intermediate. This one-pot reaction was successfully scaled-up to 1 mL of aniline in which the N-phenyl pyrroline was isolated in 95% yield. The versatility of the reaction in which 3-methyl-1-phenyl pyrroline was prepared in two-steps was demonstrated.

A convenient one-pot synthesis of N-aryl-3-pyrrolines

N-propargylanilines under one-pot homologation conditions, undergo an in situ cyclisation catalysed by Cu(I) to yield 3-pyrrolines in good yield.

A Facile Synthesis of 3-Pyrrolines

N-Substituted 3-pyrrolines were conveniently synthesized in high yield by the treatment of primary amines with cis-2-butene-1,4-diol dimesylate, which was generated from cis-1,4-butenediol.