33116-78-8

Upstream product

• 10395-46-7 1S,3R,4S,6R-(+)-3β,4β-caranediol 
• 498-15-7 (+)-Δ³-carene 
• 22556-08-7 trans-3,4-caranediol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 936-92-5 (1S,3R,4S,6R)-3,4-epoxy-3,7,7-trimethylbicyclo[4.1.0]heptane 
• 10395-46-7 (+)-3α,4β-caranediol 
• 36482-69-6 (1R,4S,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one 
• 1114568-38-5 (1S,3R,4R,6R)-3,7,7-trimethyl-4-(phenylselenyl)bicyclo[4.1.0]heptan-3-ol 
• 1196995-02-4 (1S,3S,4S,6R)-3,7,7-trimethyl-4-(phenylselanyl)bicyclo[4.1.0]heptan-3-ol 

Relevant academic research and scientific papers

Syntheses and reactions of terpene β-hydroxyselenides and β-hydroxydiselenides

A convenient method for the synthesis of optically active trans-hydroxyselenides and trans-hydroxydiselenides from the bicyclic terpene group based on the reactions of sodium selenide or sodium diselenide with cis- and trans-(+)-3-carane, trans-(+)-2-carane and (-)-β-pinane epoxides is described. The corresponding cis-hydroxy and cis-methoxydiselenides were obtained in the reaction of sodium diselenide with β-hydroxy- and β-methoxytosylates. The influence of a hydroxy group at the β-position on the diastereomeric ratio of the products of the asymmetric methoxyselenenylation of styrene has been established by composition of the products, crystal structure analyses, and theoretical calculations using a DFT method on the B3LYP level (6-311G(d)).

Syntheses of the optically active terpene hydroxyphenylselenides

The optically active hydroxyphenylselenides derived from the p-menthane, carane, and pinane systems have been obtained. Two methods of hydroxyphenylselenides synthesis have been compared. The first method is based on the reaction of alkenes with N-(phenylseleno)succinimide in the presence of water, and the second from epoxides as a result of the reaction with sodium benzeneselenolate. The influence of the substrate structures on the composition of the obtained products has been demonstrated.

STEREOCHEMISTRY OF THE CARANE SYSTEM. OXIDATION PRODUCTS OF ISOMERIC 3,4-CARANEDIOLS OBTAINED FROM (+)-3-CARENE

Oxidation of four isomeric 3,4-caranediols has been carried out and reaction products have been investigated.It has been found that cis-diols rather form cyclic ketals than are oxidized under conditions of the Jones reaction.The key intermediate for syntheses of chrysanthemic acid, (-)-2-acetonyl-3,3-dimethylcyclopropaneacetic acid was obtained exclusively by oxidation of (-)-3β,4α-caranediol.