38741-11-6

Upstream product

• 498-15-7 (+)-Δ³-carene 
• 936-92-5 (1S,3R,4S,6R)-3,4-epoxy-3,7,7-trimethylbicyclo[4.1.0]heptane 
• 13466-78-9 3-carene 
• 936-91-4 (1S,3R,4S,6R)-3,4-epoxycarane 
• 936-91-4 α-3,4-Epoxycarane 

Downstream Products

• 22556-08-7 trans-3,4-caranediol 
• 58930-63-5 (3¹R,3³S)-3²,3²-dimethyl-3(1,3)cyclopropyla-5-oxohexanoic acid 
• 24348-06-9 (+)-3β-hydroxy-4-caranone 
• 936-92-5 (1S,3R,4S,6R)-3,4-epoxy-3,7,7-trimethylbicyclo[4.1.0]heptane 
• 36482-69-6 (1R,4S,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one 
• 10395-46-7 (+)-3α,4β-caranediol 
• 33116-78-8 (1S,3R)-(+)-3-hydroxy-4-isocaranyl tosylate 

Relevant academic research and scientific papers

Monoterpenediol insect repellents

An insect repellent comprising as an active ingredient a monoterpenediol compound having the formula, STR1 wherein R1, R2 and R3 have either one of the following definitions: (i) all of R1, R2 and R3 are hydrogen, (ii) R1 is hydrogen and R2 and R3, taken together, form a carbon-carbon single bond, or (iii) R2 is hydrogen, R1 and R3, taken together, form a carbon-carbon single bond, and the hydroxyl bonded to the carbon atom marked with an asterisk takes an α-configuration.

ONE-POT TWO-STEP SYNTHESIS OF 1,2-DIOL

Diols can be prepared by hydroxilation of alkenes with m-chloroperoxybenzoic acid in water.The process occurs with high yield and complete anti stereospecificity.

Transformations of 3-carene oxide at rhenium-containing catalysts

The transformations of 3-carene oxide at rhenium-containing catalysts were studied.The introduction of rhenium into the catalytic system significantly increases the reaction rate and leads to the formation of compounds not previously encountered in the products from the isomerization of 3-carene oxide, i.e., 3-carene, 3(10),4-caradiene, 3,3,6-trimethylcycloheptanone, and 3-caren-10-ol.

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.