1-acetyl-9,10-dihydrolysergol | 955957-38-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 麦角林及其衍生物
• 英文名称: 1-acetyl-9,10-dihydrolysergol
• 英文别名: 1-[(6aR,9R,10aR)-9-(hydroxymethyl)-7-methyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinolin-4-yl]ethanone
• CAS: 955957-38-7
• 化学式: C₁₈H₂₂N₂O₂
• 分子量: 298.385
• InChiKey: PJRURPYYGHIRMY-SRCQZFHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-acetyl-9,10-dihydrolysergol 在 二甲基亚砜 、 N,N-二异丙基乙胺 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 以62%的产率得到(6aR,9R,10aR)-4-acetyl-7-methyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-carbaldehyde
  参考文献：
  名称：

  Studies on oxidation of ergot alkaloids: oxidation and desaturation of dihydrolysergol—stereochemical requirements

  摘要：

  A new method for the oxidation of ergoline alcohols to aldehydes was found (TFFA-DMSO, -78 degrees C, then DIPEA). Structural features of ergolines required for successful C7-C8 double bond introduction via Polonovski-Potier reaction of respective 6-N-oxides were defined and experimentally confirmed: (i) the presence of electron-withdrawing group at C-8; (ii) trans-diaxial orientation of N6-O and C7-H bonds ( both requirements are fulfilled for dihydrolyserg-17-al and its 2,4-dinitrophenyl hydrazone prepared in this work). (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.07.099
• 作为产物：
  描述：

  在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以210 mg的产率得到1-acetyl-9,10-dihydrolysergol
  参考文献：
  名称：

  Studies on oxidation of ergot alkaloids: oxidation and desaturation of dihydrolysergol—stereochemical requirements

  摘要：

  A new method for the oxidation of ergoline alcohols to aldehydes was found (TFFA-DMSO, -78 degrees C, then DIPEA). Structural features of ergolines required for successful C7-C8 double bond introduction via Polonovski-Potier reaction of respective 6-N-oxides were defined and experimentally confirmed: (i) the presence of electron-withdrawing group at C-8; (ii) trans-diaxial orientation of N6-O and C7-H bonds ( both requirements are fulfilled for dihydrolyserg-17-al and its 2,4-dinitrophenyl hydrazone prepared in this work). (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.07.099