trans-4'-iso-propyl-4-nitrostilbene | 345667-61-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: trans-4'-iso-propyl-4-nitrostilbene
• 英文别名: 4'-Isopropyl-4-nitrostilbene, (E)-；1-[(E)-2-(4-nitrophenyl)ethenyl]-4-propan-2-ylbenzene
• CAS: 345667-61-0
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: AVHQSZUZIFHYNU-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二乙基(4-硝基苯甲基)磷酸盐 、 4-异丙基苯甲醛 生成 cis-4'-iso-propyl-4-nitrostilbene 、 trans-4'-iso-propyl-4-nitrostilbene
  参考文献：
  名称：

  The effects of 4′-alkyl substituents on the mutagenic activity of 4-amino- and 4-nitrostilbenes in Salmonella typhimurium

  摘要：

  Six derivatives of trans-4-aminostilbene bearing different alkyl groups in the 4'-position and six of the corresponding nitro compounds were synthesized and tested for their mutagenic potency in Salmonella typhimurium strains TA98 and TA100. Regarding the test series in presence of SE-mix, maximum activity was observed for those trans-4-aminostilbenes and trans-4-nitrostilbenes bearing small alkyl substituents like methyl and ethyl. More bulky substituents reduced the mutagenic potential in the order iso-propyl < sec-butyl < tert-butyl for the aminostilbenes. The corresponding nitrostilbenes showed a similar trend under these conditions although the mutagenic activity of the tert-butyl-substituted compound was unexpectedly high in TA100. In the series without metabolic activation the nitrostilbenes showed a continuous decrease of mutagenic activity with the size of the substituents (methyl > ethyl > iso-propyl > sec-butyl > tert-butyl). These trends have been compared with quantitative structure activity relationship (QSAR) model predictions, leading to the conclusion that steric demand is an important factor for mutagenicity of substituted aminostilbenes and nitrostilbenes. The unexpected result for the tert-butyl nitrostilbene tested with metabolic activation may be attributed to a different metabolic pathway. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s1383-5718(01)00142-5

文献信息

• The effects of 4′-alkyl substituents on the mutagenic activity of 4-amino- and 4-nitrostilbenes in Salmonella typhimurium
  作者：Björn Ludolph、Markus Klein、Lothar Erdinger、Gernot Boche

  DOI：10.1016/s1383-5718(01)00142-5

  日期：2001.4

  Six derivatives of trans-4-aminostilbene bearing different alkyl groups in the 4'-position and six of the corresponding nitro compounds were synthesized and tested for their mutagenic potency in Salmonella typhimurium strains TA98 and TA100. Regarding the test series in presence of SE-mix, maximum activity was observed for those trans-4-aminostilbenes and trans-4-nitrostilbenes bearing small alkyl substituents like methyl and ethyl. More bulky substituents reduced the mutagenic potential in the order iso-propyl < sec-butyl < tert-butyl for the aminostilbenes. The corresponding nitrostilbenes showed a similar trend under these conditions although the mutagenic activity of the tert-butyl-substituted compound was unexpectedly high in TA100. In the series without metabolic activation the nitrostilbenes showed a continuous decrease of mutagenic activity with the size of the substituents (methyl > ethyl > iso-propyl > sec-butyl > tert-butyl). These trends have been compared with quantitative structure activity relationship (QSAR) model predictions, leading to the conclusion that steric demand is an important factor for mutagenicity of substituted aminostilbenes and nitrostilbenes. The unexpected result for the tert-butyl nitrostilbene tested with metabolic activation may be attributed to a different metabolic pathway. (C) 2001 Elsevier Science B.V. All rights reserved.