trans-(5R,7R,8R,9S,10R)-labda-12,14-diene-7α,8β-diol | 1400572-73-7

• 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: trans-(5R,7R,8R,9S,10R)-labda-12,14-diene-7α,8β-diol
• 英文别名: (-)-nidorellol；(2R,3R,4S,4aR,8aR)-3,4a,8,8-tetramethyl-4-[(2E)-3-methylpenta-2,4-dienyl]-2,4,5,6,7,8a-hexahydro-1H-naphthalene-2,3-diol
• CAS: 1400572-73-7
• 化学式: C₂₀H₃₄O₂
• 分子量: 306.489
• InChiKey: MVPAUVKWONUNAG-OVEYIJDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  trans-(5R,7R,8R,9S,10R)-labda-12,14-diene-7α,8β-diol 在 臭氧 作用下， 以 水 、 丙酮 为溶剂， 反应 507.0h， 生成 (3aR,4R,5aR,9aR,9bS)-4-hydroxy-3a,6,6,9a-tetramethyl-1,4,5,5a,7,8,9,9b-octahydrobenzo[e][1]benzofuran-2-one
  参考文献：
  名称：

  Synthesis of ent-ambrox® from (−)-nidorellol

  摘要：

  Using ozonolysis of the acid-catalyzed cyclized products of (-)-nidorellol and air-autoxidation as the key steps, (+)-ambrox was obtained in 53% overall yield. In the course of our synthesis, we discovered that (-)-nidorellol provided (+)-ambrox instead of the expected product, (-)-ambrox. Thus the absolute configuration of (-)-nidorellol was proved to be trans-(5R*,7R*,8R*,9S*,10R*)-labda-12,14-diene-7 alpha,8 beta-diol, which is opposite to that illustrated in a previous report. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.120

文献信息

• Synthesis of ent-ambrox® from (−)-nidorellol
  作者：Sunisa Suwancharoen、Surachai Pornpakakul、Nongnuj Muangsin

  DOI：10.1016/j.tetlet.2012.07.120

  日期：2012.10

  Using ozonolysis of the acid-catalyzed cyclized products of (-)-nidorellol and air-autoxidation as the key steps, (+)-ambrox was obtained in 53% overall yield. In the course of our synthesis, we discovered that (-)-nidorellol provided (+)-ambrox instead of the expected product, (-)-ambrox. Thus the absolute configuration of (-)-nidorellol was proved to be trans-(5R*,7R*,8R*,9S*,10R*)-labda-12,14-diene-7 alpha,8 beta-diol, which is opposite to that illustrated in a previous report. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.