[3-(2,5-Dimethylphenyl)-2,8-dioxo-1-azaspiro[4.5]dec-3-en-4-yl] 2-(4-methoxyphenyl)acetate | 1374226-58-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [3-(2,5-Dimethylphenyl)-2,8-dioxo-1-azaspiro[4.5]dec-3-en-4-yl] 2-(4-methoxyphenyl)acetate
• 英文别名: [3-(2,5-dimethylphenyl)-2,8-dioxo-1-azaspiro[4.5]dec-3-en-4-yl] 2-(4-methoxyphenyl)acetate
• CAS: 1374226-58-0
• 化学式: C₂₆H₂₇NO₅
• 分子量: 433.504
• InChiKey: ZMUUYAASUNJJHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-氨基-4-恶环己烷羧酸乙烯 在 盐酸 、 4-二甲氨基吡啶 、 potassium tert-butylate 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 12.0h， 生成 [3-(2,5-Dimethylphenyl)-2,8-dioxo-1-azaspiro[4.5]dec-3-en-4-yl] 2-(4-methoxyphenyl)acetate
  参考文献：
  名称：

  Design, Synthesis, and Analysis of the Quantitative Structure–Activity Relationships of 4-Phenyl-acyl-substituted 3-(2,5-Dimethylphenyl)-4-hydroxy-1-azaspiro[4.5]dec-3-ene-2,8-dione Derivatives

  摘要：

  A series of 4-phenyl-acyl-substituted 3-(2,5-dimethylphenyl)-4-hydroxy-1-azaspiro[4.5]dec-3-ene-2,8-dione derivatives were designed and synthesized, and their structures were characterized using H-1 NMR (or C-13 NMR), mass spectrometry, and elemental analysis. The bioactivities of the new compounds were evaluated. These compounds exhibited good inhibition activities against bean aphids (Aphis fabae) and carmine spider mite (Tetranychus cinnabarinus), and 4-phenyl acyl esters showed stronger bioactivity than 4-arylesterases and alkyl esters. The results showed that compound 8-I-e, which contains a para-methoxy group on the phenyl acyl, and compound 8-I-m, which contains a para-trifluoromethyl group on the phenyl acyl, displayed potent insecticidal activity against A. fabae and T. cinnabarinus respectively. The insecticidal activity showed a clear structure-activity relationship, confirming the importance of the flexible bridge. The DFT/B3LYP/6-31(d) level method was used to calculate molecular geometries and electronic descriptors. These factors included total energy, charge distribution, and the linear orbital level of the title compounds. Quantitative structure-activity relationship studies were performed on these compounds using quantum-chemical and physicochemical parameters as independent variables and insecticidal activity as a dependent variable. Insecticidal activity was most closely correlated (r > 0.8) with quantum chemical and physicochemical parameters.

  DOI：

  10.1021/jf3002069

文献信息

• Design, Synthesis, and Analysis of the Quantitative Structure–Activity Relationships of 4-Phenyl-acyl-substituted 3-(2,5-Dimethylphenyl)-4-hydroxy-1-azaspiro[4.5]dec-3-ene-2,8-dione Derivatives
  作者：Jinhao Zhao、Jiangong Zhang、Bingrong Xu、Zongcheng Wang、Jingli Cheng、Guonian Zhu

  DOI：10.1021/jf3002069

  日期：2012.5.16

  A series of 4-phenyl-acyl-substituted 3-(2,5-dimethylphenyl)-4-hydroxy-1-azaspiro[4.5]dec-3-ene-2,8-dione derivatives were designed and synthesized, and their structures were characterized using H-1 NMR (or C-13 NMR), mass spectrometry, and elemental analysis. The bioactivities of the new compounds were evaluated. These compounds exhibited good inhibition activities against bean aphids (Aphis fabae) and carmine spider mite (Tetranychus cinnabarinus), and 4-phenyl acyl esters showed stronger bioactivity than 4-arylesterases and alkyl esters. The results showed that compound 8-I-e, which contains a para-methoxy group on the phenyl acyl, and compound 8-I-m, which contains a para-trifluoromethyl group on the phenyl acyl, displayed potent insecticidal activity against A. fabae and T. cinnabarinus respectively. The insecticidal activity showed a clear structure-activity relationship, confirming the importance of the flexible bridge. The DFT/B3LYP/6-31(d) level method was used to calculate molecular geometries and electronic descriptors. These factors included total energy, charge distribution, and the linear orbital level of the title compounds. Quantitative structure-activity relationship studies were performed on these compounds using quantum-chemical and physicochemical parameters as independent variables and insecticidal activity as a dependent variable. Insecticidal activity was most closely correlated (r > 0.8) with quantum chemical and physicochemical parameters.