The synthesis of 2,2-dimethyl-3-(2'-chloro-3',3',3'-trifluoro-1-propenyl) cyclopropanecarboxylic acid-α-substituent p-methoxymethylbenzyl esters and it's biological activities

Abstract

The synthesis of the title acid as well as p-MeOCH2C6H4CHROH (R = H, CYCH) and p-MeOCH2C6H4CHO are reported. The (+)-cis and (-)-cis acids were obtained by resoln. of the (?-cis-acids. (?-Cis, (+)-cis, (-)-cis acids were esterified with the alcs. and the aldehyde to give esters I (R = H, cyano, CYCH). To establish the influence of the absolute configuration at the chiral centers of the acid on the biol. activity of I, the activity of the esters were tested. The results showed that the (+)-cis isomer exhibited the highest activity.

Key words: BIOLOGICAL ACTIVITY, SYNTHETIC PYRETHROID-INSECTICIDES, PYRETHRINS, CYCLOPROPANE P, BENZALCOHOL P, CYCLOPROPANE CARBOXYLIC ACID P, ORGANO FLUORINE COMPOUNDS, MESOTOMY, ORGANOCHLORINE INSECTICIDES, CONFIGURATION, PROPENYL GROUP, ORGANOFLUORINE INSECTICIDES

CLC Number:

O629

Cite this article

GU KEQUAN;WANG XUESHENG. The synthesis of 2,2-dimethyl-3-(2'-chloro-3',3',3'-trifluoro-1-propenyl) cyclopropanecarboxylic acid-α-substituent p-methoxymethylbenzyl esters and it's biological activities[J]. Chin. J. Org. Chem., 1989, 9(1): 75-80.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Mingjia Guang, Shuo Jiang, Baoyu Zhu, Rusong Zhang, Kunpeng Wang, Minghui Wang, Liangzhong Xu. Design, Synthesis and Insecticidal, Acaricidal Activities of Novel Pyrrole-2-carboxylic Acid and Their Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2895-2904.
[2]	Desheng Ning, Yuxia Fu, Lianchun Li, Zhiqi Zou, Zhenghong Pan. A New Monoterpene-Phenylpropanoid from Illicium difengpi [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1591-1595.
[3]	Qifan Wang, Yuanquan Zhang, Li Xing, Yuanxiang Zhou, Chenyu Gong, Bangcan He, Nian Zhang, Yongjun Wu, Wei Xue. Design, Synthesis and Biological Activity of Myricetin Derivatives Containing 1,2,4-Triazolo[3,4-b]-1,3,4-thiadiazole [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1525-1536.
[4]	Can Yong, Yun Li, Tao Bi, Guofeng Chen, Dongxia Zheng, Zhouyu Wang, Yuanyuan Zhang. Research Progress on the Synthesis and Activity of D-Galactose Derived Small Galectin Inhibitors [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1307-1325.
[5]	Huixin Xu, Lu Wang, Liping Zhang, Wei Liu, Qingbo Zhang, Haibo Zhang, Changsheng Zhang, Wenjun Zhang. Configurational Assignment of Malfilamentoside A and a New Furanone Glycoside Malfilamentoside D [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1229-1234.
[6]	Jie Luo, Yaqian Yan, Haoxin Wang, Yaoyao Li. Discovery of a New Polycyclic Tetramate Macrolactam Clifednamide K [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1224-1228.
[7]	Rui Ge, Yuanyuan Zhu, Haifeng Wang, Shuangxi Gu. Methods and Application of Absolute Configuration Assignment for Chiral Compounds [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 424-433.
[8]	Yajun Mao, Xiangmin Shao, Yangjie Li, Ruimei Cao, Yali Feng, Guangyu Zhai. Research Progress on the Synthesis of Quercetin Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3588-3605.
[9]	Hongliang Xu, Jing Su, Zishi Wang, Chenxin Hou, Pengchong Wu, Yue Xing, Xiangshuai Li, Xiaolei Zhu, Yuncai Lu, Lijian Xu. Synthesis, Design and Three-Dimensional Quantitative Structure Activity Relationship (3D-QSAR) Research of Phenylpyrrole Fungicides [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3560-3570.
[10]	Xiaotian Qin, Junchao Zhang, Yuqing He, Rui Zhang, Hua Cheng, Cheng Chen, Xin Qin. Synthesis and Biological Activities of Coenzyme Q Derivatives Containing (4-Aryloxylaryl)amino Moiety [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2045-2054.
[11]	Meng Xu, Shenyuan Gao, Yuanxu Zeng, Anhui Gao, Lixin Gao, Lei Xu, Yubo Zhou, Jianrong Gao, Qing Ye, Jia Li. Synthesis and Evaluation of 3-(Indol-3-yl)-4-(pyrazolo[3,4- c]pyridazin-3-yl)maleimides as Potent Mutant Isocitrate Dehydrogenase-1 Inhibitors [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1991-2000.
[12]	Ting Jiang, Hong Pu, Yanwen Duan, Xiaohui Yan, Yong Huang. New Natural Products of Streptomyces Sourced from Deep-Sea, Desert, Volcanic, and Polar Regions from 2009 to 2020 [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1804-1820.
[13]	Jun He, Xuemei Tang, Qing Zhou, Feng Peng, Tingting Liu, Liwei Liu, Ming He, Chengwei Xie, Wei Xue. Design, Synthesis and Biological Activities of Myricetin Derivatives Containing Quinazoline Thioether Moiety [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 708-718.
[14]	Zhenguo Zhang, Xiaoxiao Liu, Xinlong Zong, Yalin Yuan, Shuanglei Liu, Ting Zhang, Zishang Wu, Jingying Yang, Zhenhua Jia. Recent Advance on the Synthesis of 3,3'-Bisindolylmethane Derivatives under Transition-Metal-Free Catalytic Conditions [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 52-64.
[15]	Liang Wei, Tan Chengxia, Weng Jianquan, Liu Xinghai. Advances on Synthesis and Biological Activities of Mesoionic Compounds [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2702-2713.

2,2-二甲基-3-(2'-氯3',3',3'-三氟丙烯基)环丙烷羧酸-α-取代基对甲氧甲基苄酯的合成及活性研究