黑麦震颤素B | 81771-19-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 中文名称: 黑麦震颤素B
• 英文名称: lolitrem B
• 英文别名: (1S,9R,13R,19S,22S,23S,25R,26R,28S,31S,33S,36R)-22-hydroxy-1,10,10,12,12,30,30,36-octamethyl-28-(2-methylprop-1-enyl)-11,24,27,29,32-pentaoxa-3-azadecacyclo[17.17.0.02,17.04,16.07,15.09,13.022,36.023,25.023,33.026,31]hexatriaconta-2(17),4(16),5,7(15)-tetraen-8-one
• CAS: 81771-19-9
• 化学式: C₄₂H₅₅NO₇
• 分子量: 685.901
• InChiKey: HGBZMCXKHKZYBF-WZGHVFPCSA-N

物化性质

• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  50
• 可旋转键数：
  1
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  黑麦震颤素B 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 31-epi-lolitrem B
  参考文献：
  名称：

  Structure Elucidation of Lolitrem F, a Naturally Occurring Stereoisomer of the Tremorgenic Mycotoxin Lolitrem B, Isolated from Lolium perenne Infected with Acremonium lolii

  摘要：

  A new lolitrem, lolitrem F (2), was isolated from endophyte-infected perennial ryegrass. Its structure was shown by mass spectrometry and one- and two-dimensional NMR spectroscopy to be a 31,35-cis-fused isomer of lolitrem B. Base-catalyzed epimerization of 2 and lolitrem B (1) afforded their 31-epimers (4 and 3, respectively). Comparison with spectral data for 1 and 31-epi-lolitrem B (3) established lolitrem F to be 35-epi-lolitrem B. Compounds 1, 2, and 4 were equally tremorgenic in a mouse bioassay, but 3 was nontremorgenic. Base-catalyzed exchange of II-Si was found to permit efficient incorporation of deuterium (and potentially, therefore, of tritium) into 1 and 3.

  DOI：

  10.1021/jf950396b