17,18,19,25-tetranor-cheilanth-13(24)-en-16-al | 870692-57-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 17,18,19,25-tetranor-cheilanth-13(24)-en-16-al
• 英文别名: 2-[(1R,4aR,4bS,8aS,10aS)-4b,8,8,10a-tetramethyl-2-methylidene-1,3,4,4a,5,6,7,8a,9,10-decahydrophenanthren-1-yl]acetaldehyde
• CAS: 870692-57-2
• 化学式: C₂₁H₃₄O
• 分子量: 302.5
• InChiKey: PVCPPRIFCUIJMK-JOTVOLILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  17,18,19,25-tetranor-cheilanth-13(24)-en-16-al 在 吡啶 、 正丁基锂 、 氧气 、 rose bengal 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 17.25h， 生成 [(1R)-2-[(1S,4aR,4bS,8aS,10aR)-4b,8,8,10a-tetramethylspiro[1,3,4,4a,5,6,7,8a,9,10-decahydrophenanthrene-2,2'-oxirane]-1-yl]-1-(2-hydroxy-5-oxo-2H-furan-3-yl)ethyl] acetate
  参考文献：
  名称：

  Synthesis of Three Marine Natural Sesterterpenolides from Methyl Isoanticopalate. First Enantioselective Synthesis of Luffolide

  摘要：

  The synthesis of three marine sponge metabolites, luffolide (4), 5, and 6, are described for the first time, establishing the absolute configuration of these compounds. The key intermediate, aldehyde 17, wash obtained from methyl isoanticopalate, 11. The addition of 3-furyllithium to 17 and subsequent photochemical oxidation give the gamma-hydroxybutenolide 5 and its epimer at C-16. Sesterterpenolide 6 is obtained by dehydration of 5. From the key aldehyde 17, luffolide (4) was obtained in six steps.

  DOI：

  10.1021/jo0515529
• 作为产物：
  描述：

  (10S,14R)-(-)-isoagath-12-en-15-ol 在 四丙基高钌酸铵 水 、 sodium hexamethyldisilazane 、 对甲苯磺酸 、 N-甲基吗啉氧化物 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 18.66h， 生成 17,18,19,25-tetranor-cheilanth-13(24)-en-16-al
  参考文献：
  名称：

  Synthesis of Three Marine Natural Sesterterpenolides from Methyl Isoanticopalate. First Enantioselective Synthesis of Luffolide

  摘要：

  The synthesis of three marine sponge metabolites, luffolide (4), 5, and 6, are described for the first time, establishing the absolute configuration of these compounds. The key intermediate, aldehyde 17, wash obtained from methyl isoanticopalate, 11. The addition of 3-furyllithium to 17 and subsequent photochemical oxidation give the gamma-hydroxybutenolide 5 and its epimer at C-16. Sesterterpenolide 6 is obtained by dehydration of 5. From the key aldehyde 17, luffolide (4) was obtained in six steps.

  DOI：

  10.1021/jo0515529

文献信息

• Synthesis of Three Marine Natural Sesterterpenolides from Methyl Isoanticopalate. First Enantioselective Synthesis of Luffolide
  作者：P. Basabe、S. Delgado、I. S. Marcos、D. Diez、A. Diego、M. De Román、J. G. Urones

  DOI：10.1021/jo0515529

  日期：2005.11.1

  The synthesis of three marine sponge metabolites, luffolide (4), 5, and 6, are described for the first time, establishing the absolute configuration of these compounds. The key intermediate, aldehyde 17, wash obtained from methyl isoanticopalate, 11. The addition of 3-furyllithium to 17 and subsequent photochemical oxidation give the gamma-hydroxybutenolide 5 and its epimer at C-16. Sesterterpenolide 6 is obtained by dehydration of 5. From the key aldehyde 17, luffolide (4) was obtained in six steps.