82528-49-2

Upstream product

• 82528-40-3 (EZ)-6-hydroxy-2-ochtoden-1-yl trifluoroacetate 

Downstream Products

• 41370-30-3 Boll Weevil pheromone 
• 82528-47-0 5-phenylseleno-2-ochtodene-1,6-diol 
• 82528-46-9 1-hydroxy-5-phenylseleno-2-ochtoden-6-one 
• 82528-50-5 C₁₇H₂₄N₂O₃S 
• 73872-82-9 2,4-ochtodien-1,6-diol 
• 121617-96-7 (E)-2-ochtoden-1-ol tetrahydropyranyl ether 
• 121617-98-9 (Z)-2-ochtoden-1-ol tetrahydropyranyl ether 
• 30346-27-1 (E)-2-(3,3-Dimethylcyclohexylidene)ethanol 
• 26532-23-0 (Z)-3,3-Dimethylcyclohexane-Δ^1,β-ethanol 
• 26532-25-2 (E)-3,3-Dimethylcyclohexane-Δ^1,?-acetaldehyde 
• 26532-24-1 (Z)-3,3-Dimethylcyclohexane-Δ^1,?-acetaldehyde 
• 82528-53-8 (2Z)-1-hydroxy-2-ochtoden-6-one 
• 82528-42-5 (2E)-1-hydroxy-2-ochtoden-6-one 
• 82528-42-5 (EZ)-1-hydroxy-2-ochtoden-6-one 

Relevant academic research and scientific papers

Pheromone Synthesis, CXV. - Synthesis of (Z)-2-Ochtoden-1-ol, (E)-2-Ochtoden-1-al, and (Z)-2-Ochtoden-1-al, the Pheromone Components of the Boll Weevil (Anthonomus grandis)

The synthesis of geometrically pure (Z)-2-ochtoden-1-ol (1), (E)-2-ochtoden-1-al (2), and (Z)-2-ochtoden-1-al (3) was achieved starting from myrcene.

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.

NEW OCHTODANE SYNTHESES FROM MYRCENE

The ochtodane skeleton is formed stereoselectively from myrcene via acid-catalyzed cyclization of the benzenesulfenyl chloride adduct and the epoxide in a biogenetic type fashion.Its application to the syntheses of two ochtodane-type monoterpenes, an aldehyde component of the boll weevil pheromone and a diol found in the red alga Ochtodes crockeri, is reported.