(1S,3Z,7S,8S,11S,12S)-(+)-7,8-epoxyverticill-3-en-12,20-diol | 1103491-72-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3Z,7S,8S,11S,12S)-(+)-7,8-epoxyverticill-3-en-12,20-diol
• 英文别名: (1S,4S,6S,9Z,12S,15S)-9-(hydroxymethyl)-4,15,16,16-tetramethyl-5-oxatricyclo[10.3.1.04,6]hexadec-9-en-15-ol
• CAS: 1103491-72-0
• 化学式: C₂₀H₃₄O₃
• 分子量: 322.488
• InChiKey: QAOCILWSSJVYIO-CJFOZEQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  53
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1S,3Z,7S,8S,11S,12S)-(+)-7,8-epoxyverticill-3-en-12,20-diol 20 acetate 在 sodium hydroxide 、 水 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以64%的产率得到(1S,3Z,7S,8S,11S,12S)-(+)-7,8-epoxyverticill-3-en-12,20-diol
  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