(2S,3aS,5aS,9R,9aS,11aR)-2,5a,9,11a-tetramethyl-3-methylenedodecahydro-4H-pentaleno[6a,1-c]inden-2-ol | 371766-36-8

• 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: (2S,3aS,5aS,9R,9aS,11aR)-2,5a,9,11a-tetramethyl-3-methylenedodecahydro-4H-pentaleno[6a,1-c]inden-2-ol
• 英文别名: (1S,4S,8R,9S,12R,14R)-4,8,12,14-tetramethyl-15-methylidenetetracyclo[7.6.0.01,12.04,9]pentadecan-14-ol
• CAS: 371766-36-8
• 化学式: C₂₀H₃₂O
• 分子量: 288.473
• InChiKey: PCLSUDHVDKXZQO-LQYQHUGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2S,3aS,5aS,9R,9aS,11aR)-2,5a,9,11a-tetramethyl-3-methylenedodecahydro-4H-pentaleno[6a,1-c]inden-2-ol 在 N-溴代丁二酰亚胺(NBS) 、 三甲基氯硅烷 、 sodium iodide 作用下， 以 四氯化碳 、 正己烷 、 乙腈 为溶剂， 反应 5.25h， 生成 (3aR,5aS,9R,9aS,11aR)-3-hydroxymethyl-2,5a,9,11a-tetramethyl-1,5,5a,6,7,8,9,10,11,11a-decahydro-4H-pentaleno[6a,1-c]indene
  参考文献：
  名称：

  摘要：

  The tetracyclic diterpene waihoensene has been identified in some specimens of Podocarpus totara, particularly in a varietal form, P. totara var. waihoensis. We detail the structural analysis of this unique compound by nuclear magnetic resonance (NMR) correlation experiments, and describe some chemistry conducted on a previously reported tetracyclic alkene, the product of acid-induced rearrangement of the fenestrane diterpene lauren-1-ene. This work establishes an interrelationship between the triquinane structures of laurenene and waihoensene.

  DOI：

  10.1071/ch01056
• 作为产物：
  描述：

  [5aS-(3aS*,5aα,9α,9aR*,11aα)]-1,5,5a,6,7,8,9,10,11,11a-decahydro-2,3,5a,9,11a-pentamethyl-4H-pentaleno[6a,1-c]indene 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 以61%的产率得到(2S,3aS,5aS,9R,9aS,11aR)-2,5a,9,11a-tetramethyl-3-methylenedodecahydro-4H-pentaleno[6a,1-c]inden-2-ol
  参考文献：
  名称：

  摘要：

  The tetracyclic diterpene waihoensene has been identified in some specimens of Podocarpus totara, particularly in a varietal form, P. totara var. waihoensis. We detail the structural analysis of this unique compound by nuclear magnetic resonance (NMR) correlation experiments, and describe some chemistry conducted on a previously reported tetracyclic alkene, the product of acid-induced rearrangement of the fenestrane diterpene lauren-1-ene. This work establishes an interrelationship between the triquinane structures of laurenene and waihoensene.

  DOI：

  10.1071/ch01056

文献信息

• Waihoensene. A new laurenene-related diterpene from Podocarpus totara var waihoensis
  作者：Don B. Clarke、Simon F.R. Hinkley、Rex T. Weavers

  DOI：10.1016/s0040-4039(97)00884-8

  日期：1997.6

  New natural sources are reported for the unique rosettane diterpene, (−)-lauren-1-ene (1) along with the structure of the first laurenene-related plant metabolite. This new compound (4), isolated from the New Zealand podocarp, Podocarpus totara var waihoensis and named waihoensene, has a perhydro-4H-pentaleno[6a,1-c]indene ring system. Waihoensene is a double bond position isomer of a compound which

  据报道，独特的玫瑰烯二萜（-）-月桂烯-1-烯（1）的新自然来源以及首个与月桂烯有关的植物代谢物的结构。该新化合物（4）分离自新西兰罗汉松罗汉松（Podocarpus totara var waihoensis），命名为waihoensene，具有全氢4H-戊烯[6a，1- c ]茚环体系。Waihoensene是化合物的双键位置异构体，该化合物先前已通过对月桂烯进行酸处理而形成。