(8S,8aS)-8-hydroxy-8-methyl-6(Z)-<2'(S)-methylhexylidene>-1-azabicyclo<4.3.0>nonane | 92470-99-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 普米里奥毒素、同普米里奥毒素和别普米里奥毒素
• 英文名称: (8S,8aS)-8-hydroxy-8-methyl-6(Z)-<2'(S)-methylhexylidene>-1-azabicyclo<4.3.0>nonane
• 英文别名: pumiliotoxin 251D；C-11 epi-pumiliotoxin 251D；(6Z,8S,8aS)-8-methyl-6-[(2S)-2-methylhexylidene]-1,2,3,5,7,8a-hexahydroindolizin-8-ol
• CAS: 92470-99-0
• 化学式: C₁₆H₂₉NO
• 分子量: 251.412
• InChiKey: OKTQTXDNHCOLHT-XZFLNZQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (8S,8aS)-8-hydroxy-8-methyl-6(E)-<1'-iodo-2'(RS)-methylhexylidene>-1-azabicyclo<4.3.0>nonane 在 甲醇 、 正丁基锂 作用下， 生成 (+)-Pumiliotoxin 251D 、 (8S,8aS)-8-hydroxy-8-methyl-6(Z)-<2'(S)-methylhexylidene>-1-azabicyclo<4.3.0>nonane
  参考文献：
  名称：

  Toxicity of Pumiliotoxin 251D and Synthetic Analogs to the Cotton Pest Heliothis virescens

  摘要：

  A series of 13 simplified analogs of frog skin derived pumiliotoxin indolizidine alkaloids was prepared and evaluated for their toxicity to the larvae of the important cotton pest Heliothis virescens. The alkyl side chain of pumiliotoxin 251D was replaced with a variety of substituents designed to influence or restrict-its conformation and its ability to act as a site of metabolic detoxification. Significantly, a substituent in the R configuration at the C-2' carbon of the side chain was required for toxicity. Computational studies suggested that this substituent may control the active conformation of the side chain. No structural modification led to a significant improvement in toxicity over the natural product.

  DOI：

  10.1021/jf00052a037

文献信息

• Enantioselective total syntheses of pumiliotoxin B and pumiliotoxin 251D. A general entry to the pumiliotoxin A alkaloids via stereospecific iminium ion-vinylsilane cyclizations
  作者：Larry E. Overman、Kenneth L. Bell、Fumitaka Ito

  DOI：10.1021/ja00327a022

  日期：1984.7
• Toxicity of Pumiliotoxin 251D and Synthetic Analogs to the Cotton Pest Heliothis virescens
  作者：Thomas M. Bargar、Renee M. Lett、Peter L. Johnson、James E. Hunter、C. P. Chang、Daniel J. Pernich、Mark R. Sabol、Michael R. Dick

  DOI：10.1021/jf00052a037

  日期：1995.4

  A series of 13 simplified analogs of frog skin derived pumiliotoxin indolizidine alkaloids was prepared and evaluated for their toxicity to the larvae of the important cotton pest Heliothis virescens. The alkyl side chain of pumiliotoxin 251D was replaced with a variety of substituents designed to influence or restrict-its conformation and its ability to act as a site of metabolic detoxification. Significantly, a substituent in the R configuration at the C-2' carbon of the side chain was required for toxicity. Computational studies suggested that this substituent may control the active conformation of the side chain. No structural modification led to a significant improvement in toxicity over the natural product.