(1S)-2-[(1R,5S,6R,8aR)-1,5,6-trimethyl-5-(4-methylpent-4-enyl)-2,3,6,7,8,8a-hexahydronaphthalen-1-yl]-1-(furan-3-yl)ethanol | 946052-09-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (1S)-2-[(1R,5S,6R,8aR)-1,5,6-trimethyl-5-(4-methylpent-4-enyl)-2,3,6,7,8,8a-hexahydronaphthalen-1-yl]-1-(furan-3-yl)ethanol
• CAS: 946052-09-1
• 化学式: C₂₅H₃₈O₂
• 分子量: 370.576
• InChiKey: PVUVESDYYAEGPI-QOGRTLFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S)-2-[(1R,5S,6R,8aR)-1,5,6-trimethyl-5-(4-methylpent-4-enyl)-2,3,6,7,8,8a-hexahydronaphthalen-1-yl]-1-(furan-3-yl)ethanol 在 氧气 、 rose bengal 、 N,N-二异丙基乙胺 、 草酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.5h， 以89%的产率得到3-[(1S)-2-[(1R,5S,6R,8aR)-1,5,6-trimethyl-5-(4-methylpent-4-enyl)-2,3,6,7,8,8a-hexahydronaphthalen-1-yl]-1-hydroxyethyl]-2-hydroxy-2H-furan-5-one
  参考文献：
  名称：

  Synthesis of novel antitumoural analogues of dysidiolide from ent-halimic acid

  摘要：

  Several sesterterpenolides analogues of dysidiolide have been synthesized and their in vitro antitumoural activity against human HeLa, A549, HT-29 and HL-60 carcinoma cells is presented. The proliferation inhibition data showed a significant antitumour activity of the compounds 1b, 2a, 2b, 3a, 3b, 4a, 4b, 5, inhibiting proliferation of distinct cancer cell types with an IC50 in the low micromolar range. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.06.007
• 作为产物：
  描述：

  3-溴呋喃 、 16(13->14)abeo-18a-homo-ent-halima-1(10),14-dien-18-al 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以49%的产率得到(1R)-2-[(1R,5S,6R,8aR)-1,5,6-trimethyl-5-(4-methylpent-4-enyl)-2,3,6,7,8,8a-hexahydronaphthalen-1-yl]-1-(furan-3-yl)ethanol
  参考文献：
  名称：

  Synthesis of novel antitumoural analogues of dysidiolide from ent-halimic acid

  摘要：

  Several sesterterpenolides analogues of dysidiolide have been synthesized and their in vitro antitumoural activity against human HeLa, A549, HT-29 and HL-60 carcinoma cells is presented. The proliferation inhibition data showed a significant antitumour activity of the compounds 1b, 2a, 2b, 3a, 3b, 4a, 4b, 5, inhibiting proliferation of distinct cancer cell types with an IC50 in the low micromolar range. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.06.007