synthesis of 4-(2,6,6-trimethyl -2-cyclohexen-1-yl) -3-buten-2-ketoxime-n-o-alkyl ethers合成4 -(2,6,6-trimethyl 2-cyclohexen-1-yl)3 -buten-2 -ketoxime-n-o-alkyl醚.pdfVIP

Molecules 2005, 10, 990–999 molecules ISSN 1420-3049 Synthesis of 4-(2,6,6-Trimethyl -2-Cyclohexen-1-yl) -3-Buten- 2-Ketoxime-N-O-Alkyl Ethers Tirthankar Banerjee and Prem Dureja* Division of Agricultural Chemicals, Indian Agricultural Research Institute, New Delhi – 110 012 India *Author to whom correspondence should be addressed; E-mail: Pd_dureja@ Received: 2 April 2004; in revised form: 23 April 2005 / Accepted: 25 April 2005 / Published: 31 August 2005 Abstract: 4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-ketoxime-N-O-alkyl ethers have been synthesized starting from α-ionone, separated into their E and Z isomers and characterized on the basis of 1H-NMR and mass spectra. Keywords: α-Ionone, Condensation reaction. Introduction Interest in the oxime ether group of pesticides has grown considerably in recent years because of their overall impact on the insect endocrine system. Among the oxime ether group of insect growth regulators acetaldoxime ether showed high activity against M. domestica [1]. A variety of terpenoid juvenile hormone (JH) analogues have been introduced [2] and some of them such as methoprene are now in practical use for control of major insect pests. Most of the earlier JH analogues have terpenoid or sesquiterpenoid structures [3]. A number of oxime ethers of terpenes are also known as insect growth regulators [4]. Based on this observation, we report in this paper the synthesis of some oxime ethers of α-ionone and their separation into the corresponding E and Z isomers. Results and Discussion 4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-ketoxime needed for preparat