(1S,3Z,7S,11S,12S)-(+)-verticilla-3,8(19)-dien-7,12,20-triol 20-acetate | 1103491-78-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,3Z,7S,11S,12S)-(+)-verticilla-3,8(19)-dien-7,12,20-triol 20-acetate
• 英文别名: [(1S,3Z,7S,11S,12S)-7,12-dihydroxy-12,15,15-trimethyl-8-methylidene-4-bicyclo[9.3.1]pentadec-3-enyl]methyl acetate
• CAS: 1103491-78-6
• 化学式: C₂₂H₃₆O₄
• 分子量: 364.525
• InChiKey: GJIRORGIXAOOPP-HMJBALJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,3Z,7S,11S,12S)-(+)-verticilla-3,8(19)-dien-7,12,20-triol 20-acetate 、 乙酸酐 在 吡啶 作用下， 反应 14.0h， 生成 (1S,3Z,7S,11S,12S)-(-)-verticilla-3,8(19)-dien-7,12,20-triol 7,20-diacetate
  参考文献：
  名称：

  Oxygenated verticillene derivatives from Bursera suntui

  摘要：

  Medium polarity fractions of the hexane extracts of the stems of Bursera suntui afforded six previously known (1-6) and four hitherto unknown verticillane derivatives: (1S,3Z,7S,8S,11S,12S)-(+)-7,8-epoxyverticill-3-en-12,20-diol (7), (1S,3Z,7S,8S,11S,12S)-(+)-7,8-epoxyverticill-3-en-12,20-diol 20-acetate (8), (1S,3Z,7S,11S,12S)-(+)-verticilla-3,8(19)-dien-7,12,20-triol (9), and (1S,3Z,7S,11S,12S)-(+)-verticilla-3, 8(19)-dien-7,12,20-triol 20-acetate (10). Acetylation of 9 and 10 yielded (IS,3Z7S,1IS,12S)-(+)-verticilla-3,8(19)-dien-7,12,20-triol 7.20-diacetate (11), while hydrolysis of 8 gave 7. The structures and stereochemistry of 7-11 were established by spectroscopic analyses, particularly by 1D and 2D NMR spectra and HRESIMS. The conformational preferences of 7-11 were studied by molecular mechanics modelling employing the Monte Carlo protocol followed by B3LYP/DGDZVP DFT calculation, thus supporting the observed H-1 NMR NOESY cross peaks. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2008.09.013