4017-83-8

Basic information

• Product Name: (-)-(1R,3R,6S)-4-methylene-7,7-dimethylbicyclo[4.1.0]heptan-3-ol
• Synonyms: (-)-(1R,3R,6S)-4-methylene-7,7-dimethylbicyclo[4.1.0]heptan-3-ol
• CAS NO: 4017-83-8
• Molecular Weight: 152.236
• Mol File: 4017-83-8.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: (-)-(1R,3R,6S)-4-methylene-7,7-dimethylbicyclo[4.1.0]heptan-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(1R,3R,6S)-4-methylene-7,7-dimethylbicyclo[4.1.0]heptan-3-ol(4017-83-8)
• EPA Substance Registry System: (-)-(1R,3R,6S)-4-methylene-7,7-dimethylbicyclo[4.1.0]heptan-3-ol(4017-83-8)

Safety Data

• Hazardous Substances Data: 4017-83-8(Hazardous Substances Data)

Upstream product

• 116872-39-0 (+/-)-10-phenylsulfonylcar-3-ene 
• 10309-63-4 (-)-Caran-3β,4β-diol-4-acetat 
• 22556-08-7 trans-3,4-caranediol 
• 498-15-7 (+)-Δ³-carene 
• 10309-65-6 (-)-4α-acetoxy-3β-hydroxy-trans-carane 
• 936-91-4 3-carene epoxide 
• 4017-86-1 4-Nitro-benzoat von (-)-(1S:4R:6R)-4-Hydroxy-Δ³⁽¹⁰⁾-carven 
• 10309-64-5 (-)-(1R,3R,6S)-4-methylene-7,7-dimethylbicyclo<4.1.0>heptan-3-ol acetate 

Downstream Products

• 4017-88-3 4-isocaranol 
• 4017-89-4 (1S,3S,4R)-caran-4-ol 
• 1330616-27-7 (1S,3R,4R,6R)-7,7-dimethyl-3-(((S)-1-phenylethylamino)methyl)bicyclo[4.1.0]heptane-3,4-diol 
• 1330616-26-6 (1S,3R,4R,6R)-7,7-dimethyl-3-(((R)-1-phenylethylamino)methyl)bicyclo[4.1.0]heptane-3,4-diol 
• 1330616-23-3 (1S,3R,4R,6R)-3-(benzyl((S)-1-phenylethyl)amino)methyl-7,7-dimethylbicyclo[4.1.0]heptane-3,4-diol 
• 1330616-21-1 (1S,3R,4R,6R)-3-(benzyl((R)-1-phenylethyl)amino)methyl-7,7-dimethylbicyclo[4.1.0]heptane-3,4-diol 
• 1330616-20-0 (1S,3R,4R,6R)-3-(benzylamino)methyl-7,7-dimethylbicyclo[4.1.0]heptane-3,4-diol 
• 1330616-18-6 (1S,3R,4R,6R)-3-(dibenzylamino)methyl-7,7-dimethylbicyclo[4.1.0]heptane-3,4-diol 
• 1330616-17-5 (1S,3R,4R,6R)-3-(benzyl(methyl)amino)methyl-7,7-dimethylbicyclo[4.1.0]heptane-3,4-diol 
• 1330616-51-7 (1aR,2aR,6aR,7aS)-6a-hydroxy-1,1-dimethyl-5-((S)-1-phenylethyl)decahydro-3-oxa-5-azacyclopropa[g]naphthalene 
• 1330616-49-3 (1aR,2aR,6aR,7aS)-6a-hydroxy-1,1-dimethyl-5-((R)-1-phenylethyl)decahydro-3-oxa-5-azacyclopropa[g]naphthalene 
• 1330616-41-5 (1aR,2aR,6aR,7aS)-5-benzyl-1,1-dimethyl-6a-hydroxydecahydro-3-oxa-5-azacyclopropa[g]naphthalene 
• 4176-04-9 (1R,4S,6S)-4,7,7-Trimethyl-bicyclo[4.1.0]heptan-3-one 
• 4176-01-6 (-)-isocaranone 

Relevant articles and documents

Stereoselective Synthesis of Carane-Type Hydroxythiols and Disulfides Based on Them

Isomeric 10-sulfanylcaran-4-ols and 4-sulfanylcaran-3-ols were synthesized and used to prepare disulfides in high yields.

Synthesis of chiral thienylpyridines from naturally occurring monoterpenes: Useful ligands for cyclometallated complexes

On treatment with ammonium acetate, α,β-unsaturated ketones or aldehydes can easily undergo condensation with acetylpyridinium salts (Krohnke reaction). Four 'thienylpyridine' ligands, derived from (-)-β-pinene, (+)-camphor, (+)-3-carene and (+)-2-carene, were prepared according to this method. The multistep syntheses to get (1R,5R)-3-methylenenopinone (5), (+)-3-methylenecamphor (10), (-)-3-caren-10-al (15) and (1S,6R)-7,7-dimethyl-3-methylenebicyclo[4.1.0]heptan-2-one (18) are also described.

Acid-catalysed Terpenylations of Olivetol in the Synthesis of Cannabinoids

Examination of the toluene-p-sulphonic acid-catalysed reaction of (1S,2S,3R,6R)-(+)-trans-car-2-ene epoxide with olivetol shows that, inconsistently with the accepted mechanism, (3R,4R)-(-)-o- and -p-cannabidiols are produced as well as (3R,4R)-(-)-Δ1- and Δ6-tetrahydrocannabinols.Evidence is now presented that, as in Petrzilka's reaction employing chiral p-mentha-2,8-dien-1-ols, the reacting species is the delocalised (4R)-p-mentha-2,8-dien-1-yl cation (9).Similar terpenylation using (1S,3S,4R,6R)-(+)-trans-car-3-ene epoxide shows that besides the reported (-)-Δ6-THC, o- and p-cannabidiols, Δ1-THC and Δ4,8-iso-THC can also be produced.The nature of the products, the chirality, and the characteristics of the reaction implicate again the delocalised cation (9).Its formation via Kropp-type rearrangement is excluded and a pathway leading to (4R)-p-mentha-2,6,8-triene, which on protonation gives (9), is proposed.Protonated on C-8, the triene can be trapped and isolated as (4R)-p-mentha-2,6-dien-8-ol.The latter, made in (+/-)-form from citral, proved to be an excellent terpenylating agent for producing cannabinoids.Terpenylation of olivetol by the pinanes (1S,4S,5S)-(-)-cis-verbenol and (1R,5S,7R)-(+)-cis-chrysanthenol is compared.A major drawback of the latter is partial racemisation which occurs in the verbenone-chrysanthenone isomerisation during its photochemical preparation.Whilst Δ1-THC cannot be directly obtained from verbenol, its tertiary allylic cation permits a much higher yielding terpenylation than the secondary cation from chrysanthenol.