cis/trans-2,2-Dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylic acid hydrazide | 309274-90-6

• 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: cis/trans-2,2-Dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylic acid hydrazide
• 英文别名: 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylic acid hydrazide；3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane-1-carbohydrazide
• CAS: 309274-90-6
• 化学式: C₈H₁₂Cl₂N₂O
• 分子量: 223.102
• InChiKey: DRNSQYMFYNBCAG-UHFFFAOYSA-N

物化性质

• 沸点：
  354.3±35.0 °C(Predicted)
• 密度：
  1.387±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis/trans-2,2-Dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylic acid hydrazide 在 碳酸氢钠 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 trans-2-[2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropyl]-5-phenyl-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis and Quantitative Structure−Activity Relationships of New 2,5-Disubstituted-1,3,4-oxadiazoles

  摘要：

  Fourteen new 2,5-disubstituted-1,3,4-oxadiazoles, namely (i) six 2- [2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropyl] -5-substituted-1,3,4-oxadiazoles and (ii) eight 2-substituted-phenoxymethyl-5-substituted-aryl-1,3,4-oxadiazoles, were synthesized and evaluated for their insect growth regulatory activity against second-instar larvae of armyworm (Pseudaletia separata Walker). Two of these compounds (7 and 8) showed good insecticidal activities, with LC50 values of 14.33 and 15.85 mug/mL, respectively. Steric parameters (e.g., the molecular length d and the ratio of the nonpolar surface area and polar surface area V-1/V-2) and semiempirical quantum parameters (e.g., the molecular total energy E-t and the lowest unoccupied molecular orbital energy E-LUMO and so on) of these compounds, as well as those of six other 2,5-disubstituted-1,3,4-oxadiazoles reported, were acquired by the molecular modeling method and the PM3-SCF-MO method, respectively. With the help of the synthons' activity contribution method based on the Free-Wilson approach in its Fujita-Ban variant, quantitative structure-activity relationships were studied by regressing half-lethal concentrations against the above parameters.

  DOI：

  10.1021/jf0007941
• 作为产物：
  描述：

  3-(2,2-二氯乙烯基)-2,2-二甲基环丙烷羧酸甲酯 在 一水合肼 作用下， 反应 12.0h， 生成 cis/trans-2,2-Dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylic acid hydrazide
  参考文献：
  名称：

  Synthesis and Quantitative Structure−Activity Relationships of New 2,5-Disubstituted-1,3,4-oxadiazoles

  摘要：

  Fourteen new 2,5-disubstituted-1,3,4-oxadiazoles, namely (i) six 2- [2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropyl] -5-substituted-1,3,4-oxadiazoles and (ii) eight 2-substituted-phenoxymethyl-5-substituted-aryl-1,3,4-oxadiazoles, were synthesized and evaluated for their insect growth regulatory activity against second-instar larvae of armyworm (Pseudaletia separata Walker). Two of these compounds (7 and 8) showed good insecticidal activities, with LC50 values of 14.33 and 15.85 mug/mL, respectively. Steric parameters (e.g., the molecular length d and the ratio of the nonpolar surface area and polar surface area V-1/V-2) and semiempirical quantum parameters (e.g., the molecular total energy E-t and the lowest unoccupied molecular orbital energy E-LUMO and so on) of these compounds, as well as those of six other 2,5-disubstituted-1,3,4-oxadiazoles reported, were acquired by the molecular modeling method and the PM3-SCF-MO method, respectively. With the help of the synthons' activity contribution method based on the Free-Wilson approach in its Fujita-Ban variant, quantitative structure-activity relationships were studied by regressing half-lethal concentrations against the above parameters.

  DOI：

  10.1021/jf0007941

文献信息

• Srinivas; Subba Reddy; Yadav, Journal of Chemical Research - Part S, 2000, # 8, p. 376 - 377
  作者：Srinivas、Subba Reddy、Yadav、Ramalingam

  DOI：——

  日期：——
• Syntheses and insecticidal activities of novel 2-fluorophenyl-5-aryl/cyclopropyl-1,3,4-oxadiazoles
  作者：Wei Shi、Xuhong Qian、Gonghua Song、Rong Zhang、Rongpo Li

  DOI：10.1016/s0022-1139(00)00323-7

  日期：2000.12

  Two 2-fluorophenyl-5-substitued cyclopropyl-1,3,4-oxadiazoles (IIIa-b) with cis/trans isomers were synthesized from the corresponding hydrazide (Ia) and aroyl chlorides by two-step reactions. Six asymmetrical 2-(2,4-dichloro-5-fluorophenyl)-5-aryl-1,3,4-oxadiazoles (IIIc- h) were obtained by one step reaction of 2,4-dichloro-5-fluorobenzoic acid hydrazide (Ic) with the corresponding aromatic carboxylic acid in the presence of phosphorus oxychloride under reflux. However, the similar reaction of 4-fluorophenoxyacetic acid hydrazide (Ib) with 2,4-dichloro-5-fluorobenzoic acid failed to yield the desired asymmetrical 2-(2,4-dichloro-5-fluorophenyl)-5-(fluorophenoxymethyl)-1,3,4-oxadiazole, and the resulting product was characterized as symmetric al 2,5-bis(2,4-dichloro-5-fluorophenyl) -1,3,4-oxadiazole (DCFPO). A possible reaction mechanism is suggested. Insecticidal activities of these nine new compounds against armyworms (Pseudaletia separata Walker) were determined. (C) 2000 Elsevier Science S.A. All rights reserved.