64309-03-1

Usage

InChI:InChI=1/C16H28O2/c1-6-7-8-16(13(2)3)10-9-14(4)11-12-18-15(5)17/h6,14,16H,1-2,7-12H2,3-5H3

Upstream product

• 150-84-5 citronellyl-acetate 
• 116511-95-6 (benzenesulfonyl)methyllithium 
• 922-67-8 propynoic acid methyl ester 
• 84143-56-6 Acetic acid 6-iodomethyl-3,7-dimethyl-oct-7-enyl ester 
• 108-24-7 acetic anhydride 
• 67548-26-9 2-Methyl-2,6-heptadien-1-ol 
• 7103-09-5 4-but-1-enylmagnesium bromide 
• 7540-51-4 (S)-3,7-dimethyl-6-octen-1-ol 
• 1117-61-9 (3R)-citronellol 
• 71256-71-8 (3RS,6RS)-6-(1-Hydroxy-1-methylethyl)-3-methyl-9-decen-1-yl Acetate 
• 1787-98-0 (3RS,6RS)-6,7-Epoxycitronellyl Acetate 
• 71256-76-3 (3RS,6R)-3-methyl-6-(1-methylethenyl)dec-9-en-1-ol 
• 75-36-5 acetyl chloride 
• 7086-79-5 (R)-4-methyl-3-(3'-oxobutyl)pent-4-enal 

Relevant academic research and scientific papers

Synthesis of the Optical Isomers of 3-Methyl-6-isopropenyl-9-decen-1-yl Acetate, a Component of the California Red Scale Pheromone

The synthesis of the optical isomers of 3-methyl-6-isopropenyl-9-decen-1-yl acetate (1), a component of the California red scale pheromone, and the determination of their biological activity were completed.Initially, (+/-)-citronellol was converted in four steps to a mixture of all four diastereomers of 1, the key step being the reaction of lithium di(3-butenyl)cuprate with 6,7-epoxycitronellyl acetate (4).This mixture strongly attracted male California red scale.To determine which of the four diastereomers of 1 were biologically active, (3R,6RS)- and (3S,6RS)-1 were then prepared from (R)-(+)-citronellol and (S)-(-)-citronellol, respectively.Since the 3S,6RS diastereomeric mixture was found to be a powerful attractant whereas the 3R,6RS diastereomeric mixture was devoid of attractancy, the 3S,6R and 3S,6S diastereomers of 1 were then prepared.The key to the synthesis of each of these two diastereomers of 1 was the high-performance LC separation of the diastereomeric MTP esters 12a and 12b.Lithium aluminium hydride reduction of 12a and 12b gave the corresponding diols 11a and 11b, which were intermediates in the synthesis of (3S,6R)- and (3S,6S)-1, respectively.The assignment of absolute configuration at C-6 in diols 11a and 11b (and therefore of the diastereomers of 1) was made on the basis of induced CD spectra of each diol and of the closely related diol of (10S)-JH III (13).The 3S,6R diastereomer of 1 was found to be more attractive to male California red scale than was the 3S,6S diastereomer.The naturally occuring pheromone component 1, upon examination by capillary GLC under conditions which gave separation of the 3S,6R and 3S,6S diastereomers, eluted with the synthetic 3S,6R diastereomer.

PROCESS FOR PREPARING 6-ISOPROPENYL-3-METHYL-9-DECENYL ACETATE, AND INTERMEDIATES THEREFOR

The present invention provides a process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate (5): wherein Ac represents an acetyl group, the process comprising steps of: subjecting a 2-methyl-2,6-heptadiene compound (1) having a leaving group X at position 1: wherein X represents an acyloxy group having 1 to 10 carbon atoms including the carbon atom of the carbonyl group, an alkanesulfonyloxy group having 1 to 10 carbon atoms, an arenesulfonyloxy group having 6 to 20 carbon atoms, or a halogen atom, to a nucleophilic substitution reaction with a 3-methylpentyl nucleophilic reagent (2) having a protected hydroxyl group at position 5: wherein M represents Li, MgZ1, ZnZ1, Cu, CuZ1, or CuLiZ1, wherein Z1 represents a halogen atom or a CH2CH2CH(CH3)CH2CH2OR group, and R represents a protecting group for a hydroxyl group, to form a 6-isopropenyl-3-methyl-9-decene compound (3) having a protected hydroxyl group at position 1: wherein R is as defined above; subjecting the 6-isopropenyl-3-methyl-9-decene compound (3) having the protected hydroxyl group at position 1 to a deprotection reaction to form 6-isopropenyl-3-methyl-9-decenol (4); and acetylating 6-isopropenyl-3-methyl-9-decenol (4) to form 6-isopropenyl-3-methyl-9-decenyl acetate (5).

PROCESS FOR PREPARING 6-ISOPROPENYL-3-METHYL-9-DECENYL ACETATE AND INTERMEDIATES THEREOF

A process for process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate of the following formula (3), wherein Ac represents an acetyl group, the process comprising steps of: preparing a nucleophilic reagent, 5-isopropenyl-2-methyl-8-nonenyl compound, of the following general formula (1): wherein M1 represents Li, MgZ1, ZnZ1, Cu, CuZ1, or CuLiZ1, wherein Z1 represents a halogen atom or a 5-isopropenyl-2-methyl-8-nonenyl group, from a 5-isopropenyl-2-methyl-8-nonenyl halide compound of the following general formula (4): wherein X1 represents a halogen atom; subjecting the nucleophilic reagent (1), 5-isopropenyl-2-methyl-8-nonenyl compound, to an addition reaction with at least one electrophilic reagent selected from the group consisting of formaldehyde, paraformaldehyde, and 1,3,5-trioxane, followed by a hydrolysis reaction to form 6-isopropenyl-3-methyl-9-decenol of the following formula (2); and acetylating 6-isopropenyl-3-methyl-9-decenol (2) to form 6-isopropenyl-3-methyl-9-decenyl acetate (3).

Efficient synthesis of the Aonidiella aurantii (Mask.) sex pheromone component: (3S,6RS)-3-methyl-6-(1-methylethenyl)-9-decenyl acetate

The title compound, active component of the sex pheromone of Aonidiella aurantii (California Red Scale), was synthesized in three steps starting from S-citronellyl acetate with a 30% overall yield. The key feature of the synthesis is a copper salt assisted, highly regioselective attack of the 4-butenyl bromide Grignard reagent on the γ-site of the chloroallylic system of (S)-8-chloro-3,7-dimethyl-6-octenyl acetate (8a).

44. Vitamin-B12-Catalyzed C,C-Bond Formation. Synthesis of a California Red Scale Phermone

A mixture of (3S,6R)- and (3R,6R)-3-methyl-6-(1-methylethenyl)dec-9-enyl acetate (1a and 1b, respectively) - 1a being a phermone of the California red scale - is synthesized in 14 steps from (+)-(R)-limonene (4).The key step is the reductive vitamin-B12-catalyzed coupling of (R)-5-(2-iodoethyl)-6-methylhept-6-en-2-one ethylene acetal (8) and methyl crotonate (3).

A SIMPLE AND EFFICIENT SYNTHESIS OF 3-METHYL-6-(1-METHYLETHENYL)-9-DECEN-1-YL ACETATE A COMPONENT OF THE CALIFORNIA RED SCALE PHEROMONE

A diastereomeric mixture of (3S,6R) and (3S,6S) 3-methyl-6-(1-methylethenyl)-9-decen-1-yl acetate 1(a,b) has been synthesized in high yield starting from (S)-(-)-citronellol.The key step of the synthesis is the regioselective coupling of the benzothiazole

NEW SYNTHESIS OF THE CALIFORNIA RED SCALE SEX PHEROMONE

The target molecules 1 and 2 were synthesized from a common intermediate 6 prepared from (R)-Limonene.The first enantioselective synthesis of 2 is described.

Ethylaluminum Dichloride Catalyzed Ene Reactions of Aldehydes with Nonnucleophilic Alkenes

Ethylaluminum dichloride, which is a strong Lewis acid and a proton scavenger, catalyzes the ene reactions of aliphatic aldehydes with nonnucleophilic alkenes.Higher aldehydes give good yields of ene adducts with terminal alkenes.Formaldehyde gives good yields of adducts with electron-deficient alkenes.This reaction has been used for the synthesis of recifeiolide, ricinelaidic acid, and the insect pheromones (E,E)-8,10-dodecadienyl acetate and (E)-9,11-dodecadienyl acetate.

Intermediates for insect pheromone

Synthesis and intermediates for making insect pheromone useful in the control of red scale, Aonidiella aurantii.