Isovellerdiol | 196501-18-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Isovellerdiol
• 英文别名: [(1aR,3aR,6aR,6bS)-1a-(hydroxymethyl)-5,5,6b-trimethyl-3a,4,6,6a-tetrahydro-1H-cyclopropa[e]inden-2-yl]methanol
• CAS: 196501-18-5
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: PXOZBWDPKXNHFQ-FDEJFUCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Isovellerdiol 以83%的产率得到
  参考文献：
  名称：

  THOMPSON, SCOTT K.;HEATHCOCK, CLAYTON H., J. ORG. CHEM., 55,(1990) N 10, C. 783

  摘要：

  DOI：
• 作为产物：
  描述：

  (1aα,3aβ,6aβ,6bα)-(+/-)-3a,4,5,6,6a,6b-hexahydro-5,5,6b-trimethylcyclopropindene-1a,2(1H)-dimethanol 在 吡啶 、 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 Isovellerdiol
  参考文献：
  名称：

  The preparation and bioactivities of (−)-isovelleral1,2

  摘要：

  The resolution of synthetic (+/-)-isovelleral (1), via chromatographic separation of the two diastereomers of the (-)-menthoxyacetic acid diester of the corresponding (+/-)-diol (3), yielded both enantiomers of the bioactive fungal metabolite (+)-isovelleral (1). While the antimicrobial and cytotoxic activities of the two enantiomers are comparable, natural (+)-1 is approximately 10 times more mutagenic towards Ames' tester strain TA98 than (-)-1. The two enantiomers of the cyclopropane ring isomer 2 also possess negligible mutagenicity compared to (+)-1. Both (+)-1 and (-)-1 have the same affinity for the vanilloid receptor, but significant different affinity for the dopamine D1 receptor. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00055-2

文献信息

• THOMPSON, SCOTT K.;HEATHCOCK, CLAYTON H., J. ORG. CHEM., 55,(1990) N 10, C. 783
  作者：THOMPSON, SCOTT K.、HEATHCOCK, CLAYTON H.

  DOI：——

  日期：——
• The preparation and bioactivities of (−)-isovelleral1,2
  作者：Mikael Jonassohn、Rikard Hjertberg、Heidrun Anke、Kim Dekermendjian、Arpad Szallasi、Eckhard Thines、Robin Witt、Olov Sterner

  DOI：10.1016/s0968-0896(97)00055-2

  日期：1997.7

  The resolution of synthetic (+/-)-isovelleral (1), via chromatographic separation of the two diastereomers of the (-)-menthoxyacetic acid diester of the corresponding (+/-)-diol (3), yielded both enantiomers of the bioactive fungal metabolite (+)-isovelleral (1). While the antimicrobial and cytotoxic activities of the two enantiomers are comparable, natural (+)-1 is approximately 10 times more mutagenic towards Ames' tester strain TA98 than (-)-1. The two enantiomers of the cyclopropane ring isomer 2 also possess negligible mutagenicity compared to (+)-1. Both (+)-1 and (-)-1 have the same affinity for the vanilloid receptor, but significant different affinity for the dopamine D1 receptor. (C) 1997 Elsevier Science Ltd.