The total synthesis of 3,7-dimethyl-2-tridecanyl propionate, the active component of the sex pheromone of pine sawfly Diprion jingyuanensis is reported. The new synthesis process starts from 2-methyloctanal, then thro...The total synthesis of 3,7-dimethyl-2-tridecanyl propionate, the active component of the sex pheromone of pine sawfly Diprion jingyuanensis is reported. The new synthesis process starts from 2-methyloctanal, then through hydroxyethylenation, transetherification, Claisen rearrangement, hydroxymethylation, hydrogenation to give 3,7- dimethyl-2-tridecanol. Esterification of 3,7-dimethyl-2-tridecanol affords 3,7-dimethyl-2-tridecanyl propionate.展开更多
The total synthesis of 3,7 dimethyl 2 tridecanyl acetate,the active component of the sex pheromone of diprion pini,was investigated in this paper.The two key synthins blocks,2 methyl octan 1 yl lithium and 3,4 ...The total synthesis of 3,7 dimethyl 2 tridecanyl acetate,the active component of the sex pheromone of diprion pini,was investigated in this paper.The two key synthins blocks,2 methyl octan 1 yl lithium and 3,4 dimethyl γ butyrolactone,were obtained from diethyl malonate and 2,3 epoxybutane.2 Methyl octan 1 yl lithium reacted with 3,4 dimethyl γ butyrolactone to yield the ketoalcohol and then followed by Huang Minlong reduction to afford 3,7 dimethyl 2 tridecanol,acylated with acetic anhydide to give 3,7 dimethyl 2 tridecanyl acetate.展开更多
文摘The total synthesis of 3,7-dimethyl-2-tridecanyl propionate, the active component of the sex pheromone of pine sawfly Diprion jingyuanensis is reported. The new synthesis process starts from 2-methyloctanal, then through hydroxyethylenation, transetherification, Claisen rearrangement, hydroxymethylation, hydrogenation to give 3,7- dimethyl-2-tridecanol. Esterification of 3,7-dimethyl-2-tridecanol affords 3,7-dimethyl-2-tridecanyl propionate.
基金Supported by Foundation for University Key Teacher by the Min-istry of Education
文摘The total synthesis of 3,7 dimethyl 2 tridecanyl acetate,the active component of the sex pheromone of diprion pini,was investigated in this paper.The two key synthins blocks,2 methyl octan 1 yl lithium and 3,4 dimethyl γ butyrolactone,were obtained from diethyl malonate and 2,3 epoxybutane.2 Methyl octan 1 yl lithium reacted with 3,4 dimethyl γ butyrolactone to yield the ketoalcohol and then followed by Huang Minlong reduction to afford 3,7 dimethyl 2 tridecanol,acylated with acetic anhydide to give 3,7 dimethyl 2 tridecanyl acetate.
