94836-03-0

Upstream product

• 123-35-3 7-methyl-3-methene-1,6-octadiene 
• 931-59-9 benzenesulfenyl chloride 
• 70473-42-6 [1-(1-Chloro-1-methyl-ethyl)-4-methylene-hex-5-enylsulfanyl]-benzene 
• 80527-38-4 Acetic acid 1,1-dimethyl-5-methylene-2-phenylsulfanyl-hept-6-enyl ester 

Downstream Products

• 95495-79-7 2-(5,5-dimethyl-cyclohex-1-enyl)-ethanol 
• 95495-81-1 (5,5-dimethyl-cyclohex-1-enyl)-acetic acid 
• 82528-38-9 1-acetoxy-6-phenylthio-2-ochtodene 
• 55298-95-8 (5,5-dimethyl-cyclohex-1-enyl)-acetic acid methyl ester 
• 55298-96-9 (3,3-Dimethyl-cyclohex-1-enyl)-acetic acid methyl ester 

Relevant academic research and scientific papers

FACILE FUNCTIONALIZATION OF THE ISOPROPYLIDENE TERMINUS OF ACYCLIC MONOTERPENES BY WAY OF BENZENESULFENYL CHLORIDE ADDITION

Highly site- and regioselective terminal functionalizations of acyclic monoterpenes 1 via benzenesulfenyl chloride addition followed by hydrolysis assisted by silica gel, dehydrochlorination under neutral or weakly basic condition, or dehydrochlorination by strongly basic treatment respectively providing β-hydroxy sulfides 3, terminal methallylic sulfides 4, or vinylsulfides 5 are developed.Conversion of 4 to terminal trans-allylic alcohols 10 via sulfoxides 9 by the Evans procedure is also described.

SYNTHETIC STUDIES ON THE OCHTODANE TYPE TERPENES I. STEREOSELECTIVE CONSTRUCTION OF THE OCHTODANE SKELETON FROM MYRCENE.

The ochtodane skeleton, the Carbon framework of 1,1-dimethyl-3-ethylcyclohexane (1) was constructed highly stereoselectively by the acid-catalyzed (SnCl//4 or CF//3CO//2H) cyclization of the terminally functionalized myrcene derivatives, the benzenesulfenyl chloride adduct (7), the terminal beta -hydroxy sulfide (8) derived from 7, and myrcene 6,7-epoxide (10). The stereoselectivity of the 3-exo-double bond in 1 formed concomitantly in the cyclization reaction was found to depend remarkably upon the reaction temperture and the 85-94% of E-stereoselectivity was attained at minus 78 degree C. By the method, the ochtodane derivatives with the sulfur- or oxygen-functional groups on the C(6)-position were obtained.