(2S,3aS,5aS,9R,9aS,11aR)-2,5a,9,11a-tetramethyl-3-methylenedodecahydro-4H-pentaleno[6a,1-c]inden-2-yl acetate | 371766-39-1

• 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-yl acetate
• 英文别名: [(1S,4S,8R,9S,12R,14R)-4,8,12,14-tetramethyl-15-methylidene-14-tetracyclo[7.6.0.01,12.04,9]pentadecanyl] acetate
• CAS: 371766-39-1
• 化学式: C₂₂H₃₄O₂
• 分子量: 330.511
• InChiKey: DJTNUEQCLSJWKC-PIFREUSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

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-yl acetate 在 N-溴代丁二酰亚胺(NBS) 、 lithium 、 乙胺 作用下， 以 四氯化碳 为溶剂， 反应 2.75h， 生成 (3aR,5aS,9R,9aS,11aR)-2-hydroxymethyl-3,5a,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：

  乙酸酐 、 (2S,3aS,5aS,9R,9aS,11aR)-2,5a,9,11a-tetramethyl-3-methylenedodecahydro-4H-pentaleno[6a,1-c]inden-2-ol 在 4-二甲氨基吡啶 、 三乙胺 作用下， 反应 26.0h， 以26%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-yl acetate
  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