eudesm-3β,4β,11-triol | 253864-02-7

• 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: eudesm-3β,4β,11-triol
• 英文别名: (1R,2S,4aS,7R,8aR)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-2,3,4,5,6,7,8,8a-octahydronaphthalene-1,2-diol
• CAS: 253864-02-7
• 化学式: C₁₅H₂₈O₃
• 分子量: 256.386
• InChiKey: MIELSHSRDNXCSQ-RKEKIRQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.69
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-(-)-α-甲氧基-α-(三氟甲基)苯乙酸 、 eudesm-3β,4β,11-triol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以1.2 mg的产率得到[(1R,2S,4aS,7R,8aR)-1-hydroxy-1,4a-dimethyl-7-[2-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxypropan-2-yl]-2,3,4,5,6,7,8,8a-octahydronaphthalen-2-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  A revision of the positive sign of the optical rotation and its maximum value of α-eudesmol

  摘要：

  The ether extract of the liverwort Porella perrottetiana afforded (-)-alpha-eudesmol, which showed an opposite sign of the optical rotation to that found in higher plants. Present work on the absolute configuration and an optical purity of (-)-alpha-eudesmol strongly suggested that the positive values (e.g. + 28.5 degrees) described in many previous papers should be revised. Since the absolute configuration of (-)-alpha-eudesmol was identical to that of (+)-beta-eudesmol found in the higher plants, it was apparent that the expression of the positive sign might be revised to (-)-alpha-eudesmol. The optical purity, reconfirmation of the absolute configuration and synthesis of (-)-alpha-eudesmol will be discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00299-x
• 作为产物：
  描述：

  (4aR,7R,8aR)-4a-methyl-7-(2-triethylsilyloxypropan-2-yl)-2,3,4,5,6,7,8,8a-octahydronaphthalen-1-one 在 六甲基磷酰三胺 、 四氧化锇 、 四(三苯基膦)钯 、 四丁基氟化铵 、 双氧水 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正庚烷 、 乙基苯 为溶剂， 反应 42.0h， 生成 eudesm-3β,4β,11-triol
  参考文献：
  名称：

  A revision of the positive sign of the optical rotation and its maximum value of α-eudesmol

  摘要：

  The ether extract of the liverwort Porella perrottetiana afforded (-)-alpha-eudesmol, which showed an opposite sign of the optical rotation to that found in higher plants. Present work on the absolute configuration and an optical purity of (-)-alpha-eudesmol strongly suggested that the positive values (e.g. + 28.5 degrees) described in many previous papers should be revised. Since the absolute configuration of (-)-alpha-eudesmol was identical to that of (+)-beta-eudesmol found in the higher plants, it was apparent that the expression of the positive sign might be revised to (-)-alpha-eudesmol. The optical purity, reconfirmation of the absolute configuration and synthesis of (-)-alpha-eudesmol will be discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00299-x