127-91-3Relevant articles and documents
A Convenient Synthesis of (+)-β-Pinene from (+)-α-Pinene
Harwood, Laurence M.,Julia, Marc
, p. 456 - 457 (1980)
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Hydroboration of Terpenes. 9. A Simple Improved Procedure for Upgrading the Optical Purity of Commercially Available α- and β-Pinenes. Conversion of (+)-α-Pinene to (+)-β-Pinene via Hydroboration-Isomerisation.
Brown, Herbert C.,Joshi, Nawalkishore N.
, p. 4059 - 4062 (1988)
An improved method for the preparation of optically pure diisopinocampheylborane (Ipc2BH) from commercially available (+)- and (-)-α-pinene (91-92percent ee) is described.The procedure, which is based on selective incorporation of the major enantiomer of α-pinene in crystalline dialkylborane, is both simple and efficient.Treatment with benzaldehyde liberates the parent olefin in very high enantiomeric excess (>99.5percent).The intermediate Ipc2BH can be thermally isomerized (130 deg C, 12h) to dimyrtanylborane, which is readily converted into the otherwise inaccessible (+)-β-pinene (>99.5) percent ee).In the course of this study it was established that the optical purification of commercial (-)-β-pinene too can be easily achieved by the formation and recrystallisation of tri-cis-myrtanylborane.Thus, simple manipulations via hydroboration provide easy access to all four enantiomers of α- and β-pinenes in very high optical purity.
Contra-thermodynamic Olefin Isomerization by Chain-Walking Hydroboration and Dehydroboration
Bloomer, Brandon,Butcher, Trevor W.,Ciccia, Nicodemo R.,Conk, Richard J.,Hanna, Steven,Hartwig, John F.
supporting information, p. 1005 - 1010 (2022/02/10)
We report a dehydroboration process that can be coupled with chain-walking hydroboration to create a one-pot, contra-thermodynamic, short-or long-range isomerization of internal olefins to terminal olefins. This dehydroboration occurs by a sequence comprising activation with a nucleophile, iodination, and base-promoted elimination. The isomerization proceeds at room temperature without the need for a fluoride base, and the substrate scope of this isomerization is expanded over those of previous isomerizations we have reported with silanes.
Oxidation of α-pinene by atmospheric oxygen in the supercritical CO2-ethyl acetate system in the presence of Co(II) complexes
Anikeev,Ilina,Kurbakova,Nefedov,Volcho,Salakhutdinov
experimental part, p. 190 - 195 (2012/03/12)
The reactivity of monoterpene α-pinene in a flow reactor in the presence of cobalt catalyst in a complex supercritical solvent consisting of CO2 and ethyl acetate is studied over the temperature range of 190-320°C and a pressure range of 110-125 atm. It was found that the main isomerization products include compounds with bicyclo[2.2.1]heptane and p-menthane backbones; the reaction is accompanied by partial racemization. The formation of oxidation products is observed in the presence of air, with epoxydation rather than allylic oxidation being the predominant process at the first stage. The oxidized products (campholenic aldehyde, verbenone, pinocamphone) are shown to be formed with a high enantioselectivity; the formation of acetoxylation products is observed at temperatures above 200°C.
ORALLY EFFECTIVE CANNABINOID ANALOGS
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Page/Page column 33-35, (2008/06/13)
The present invention relates to orally effective ligands of the peripheral cannabinoid thereof, receptor CB2 especially (+)-α pinene derivatives, and to pharmaceutical compositions thereof, which are useful for prevention, alleviation or treatment of autoimmune neurodegenerative disorders, in particular multiple sclerosis and associated symptoms. Methods of the invention are useful when the active ingredient is administered alone or in combination with existing therapeutic modalities. The compositions are administered by oral route.