(Z)-1-ethoxy-1-eicosene | 1195790-16-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-1-ethoxy-1-eicosene
• CAS: 1195790-16-9
• 化学式: C₂₂H₄₄O
• 分子量: 324.591
• InChiKey: SBRJWHAUNGNBSK-DQRAZIAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.19
• 重原子数：
  23.0
• 可旋转键数：
  19.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  乙基烯丙基醚 、 1-碘十七烷 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 8.25h， 以88%的产率得到(Z)-1-ethoxy-1-eicosene
  参考文献：
  名称：

  Attempted synthesis of 3-hydroxy-2-octadecylindole. Proposed structural revision of previously prepared 3-hydroxy-2-octadecylindole and a proposed structure of fistulosin

  摘要：

  A synthetic route to 3-hydroxy-2-octadecylindole, the putative structure of the novel indole alkaloid fistulosin, starting from 2-nitro-1-iodobenzene was examined. Key steps include formation of a 1-stannyl-substituted 1-methoxy-1-alkene from a Fischer chromium carbene, intermolecular Kosugi-Migita-Stille coupling, and a palladium-catalyzed reductive N-heteroannulation. Demethylation of 3-methoxy-2-octadecylindole, a possible immediate precursor to 3-hydroxy-2-octadecylindole, was unsuccessful and gave instead methyl 2-(1-oxononadecanyl)aminobenzoate. The structure of the isolated alkaloid was suggested to be 2-(1-oxooctaclecanyl)aminobenzoate by comparison of analytical data with a synthetic sample. In addition. oxidation of 2-octadecylindole gave a 2,2'-dimer, a compound identical to previously prepared 3-hydroxy-2-octadecylindole. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.055