ethyl 3-(2,2-dichlorovinyl)-2-ethyl-2-methylcyclopropane-1-carboxylate | 1150668-60-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 3-(2,2-dichlorovinyl)-2-ethyl-2-methylcyclopropane-1-carboxylate
• 英文别名: Ethyl 3-(2,2-dichlorovinyl)-2-ethyl-2-methyl-cyclopropane-1-carboxylate；ethyl 3-(2,2-dichloroethenyl)-2-ethyl-2-methylcyclopropane-1-carboxylate
• CAS: 1150668-60-2
• 化学式: C₁₁H₁₆Cl₂O₂
• 分子量: 251.153
• InChiKey: CEALAKDRIZMDIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 3-(2,2-dichlorovinyl)-2-ethyl-2-methylcyclopropane-1-carboxylate 、 3-苯氧基苄醇 在 potassium tert-butylate 作用下， 100.0~105.0 ℃ 、266.64 Pa 条件下， 以77%的产率得到3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2-ethyl-2-methylcyclopropane-1-carboxylate
  参考文献：
  名称：

  Synthesis and biological activity of permethrin analogs containing various substituents in position 2 of the cyclopropane ring

  摘要：

  A number of permethrin derivatives having various substituents (Me, Et, Pr, Ph, PhCH2, PhCH2CH2) in position 2 of the cyclopropane ring were synthesized and assayed for insecticidal activity against typhoid flies, rice weevils, and black bean aphid and juvenile hormone activity against flour beetle chrysalises. The examined compounds showed a weak insecticidal activity. Some derivatives were found to exert knockdown effect analogous to that of commercial pyrethroid tetramethrin; however, unlike permethrin, they exhibited pronounced juvenile hormone activity.

  DOI：

  10.1134/s1070428009030026
• 作为产物：
  描述：

  ethyl 4-bromo-6,6,6-trichloro-3-ethyl-3-methylhexanoate 在 乙醇 、 sodium ethanolate 作用下， 反应 2.0h， 以52%的产率得到ethyl 3-(2,2-dichlorovinyl)-2-ethyl-2-methylcyclopropane-1-carboxylate
  参考文献：
  名称：

  Synthesis and biological activity of permethrinic acid analogs containing various substituents in position 2 of the cyclopropane ring

  摘要：

  A number of permethrinic acid ethyl ester derivatives having various substituents [Et, Pr, Ph, Ph(CH2)n (n = 1, 2), etc.] in position 2 of the cyclopropane ring were synthesized, and their insecticidal acivity against typhoid flies., rice weevils, and bean aphides, as well as juvenoid activity on flour beetle chrysalises, was studied. The newly synthesized Compounds turned out to exhibit weak insecticidal activity against standard insects but pronounced juvenile hormone activity, which differentiates them from permethrinic acid esters.

  DOI：

  10.1134/s107042800808006x

文献信息

• Synthesis and biological activity of permethrinic acid analogs containing various substituents in position 2 of the cyclopropane ring
  作者：N. S. Mirzabekova、N. E. Kuz’mina、O. I. Lukashov、N. A. Sokolova、S. N. Golosov、P. V. Kazakov、T. G. Perlova、V. V. Potapova、V. A. Kheinman、G. B. Ivanova

  DOI：10.1134/s107042800808006x

  日期：2008.8

  A number of permethrinic acid ethyl ester derivatives having various substituents [Et, Pr, Ph, Ph(CH2)n (n = 1, 2), etc.] in position 2 of the cyclopropane ring were synthesized, and their insecticidal acivity against typhoid flies., rice weevils, and bean aphides, as well as juvenoid activity on flour beetle chrysalises, was studied. The newly synthesized Compounds turned out to exhibit weak insecticidal activity against standard insects but pronounced juvenile hormone activity, which differentiates them from permethrinic acid esters.
• Synthesis and biological activity of permethrin analogs containing various substituents in position 2 of the cyclopropane ring
  作者：N. S. Mirzabekova、N. E. Kuz’mina、O. I. Lukashov、N. A. Sokolova、S. N. Golosov、P. V. Kazakov、T. G. Perlova、V. V. Potapova、V. A. Kheinman、G. B. Ivanova

  DOI：10.1134/s1070428009030026

  日期：2009.3

  A number of permethrin derivatives having various substituents (Me, Et, Pr, Ph, PhCH2, PhCH2CH2) in position 2 of the cyclopropane ring were synthesized and assayed for insecticidal activity against typhoid flies, rice weevils, and black bean aphid and juvenile hormone activity against flour beetle chrysalises. The examined compounds showed a weak insecticidal activity. Some derivatives were found to exert knockdown effect analogous to that of commercial pyrethroid tetramethrin; however, unlike permethrin, they exhibited pronounced juvenile hormone activity.