(1S)-(+)-3-Carene

The Uses of (1S)-(+)-3-Carene

Chiral building block for the preparation of bicyclo[3.2.0]heptenes that are useful intermediates in the synthesis of (+)-lineatin and both enantiomers of capnellene. Has been converted to its corresponding allenyl allylic ether for studies of its thermal isomerization chemistry. Precursor to di(4-isocaranyl)borane, an asymmetric hydroboration reagent for olefins.

Definition

ChEBI: A car-3-ene (3,7,7-trimethylbicyclo[4.1.0]hept-3-ene) that has S configuration at position 1 and R configuration at position 6.

Production Methods

3-Carene is obtained exclusively by fractional distillation of certain turpentines.

General Description

(1S)-(+)-3-Carene is a monoterpene.

Chemical Reactivity

3-Carene readily undergoes autoxidation and resinification in air. Addition of pyrogallol or resorcinol as stabilizers is recommended. On treatment with peracetic acid in glacial acetic acid and subsequent saponification, 3-carene is oxidized to 3,4- caranediol. Pyrolysis at 300–580 ℃ in the presence of Fe(III) oxide on carriers gives p-cymene as the main product.