16,17-Didehydro-5-oxo-18-(phenylsulfonyl)aspidofractinine

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 白坚木瑞亭生物碱
• 英文名称: 16,17-Didehydro-5-oxo-18-(phenylsulfonyl)aspidofractinine
• 化学式: C₂₅H₂₄N₂O₃S
• 分子量: 432.543
• InChiKey: BHRDPVFFKVWWLK-AFCFGPHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  31.0
• 可旋转键数：
  2.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  66.48
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  16,17-Didehydro-5-oxo-18-(phenylsulfonyl)aspidofractinine 在 lithium aluminium tetrahydride 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙二醇 为溶剂， 反应 23.0h， 生成 aspidospermidine
  参考文献：
  名称：

  Total Synthesis of (.+-.)-Aspidofractinine and (.+-.)-Aspidospermidine

  摘要：

  Functional group manipulations on a previously constructed, easily accessible deethylaspidospermidine derivative have transformed the latter in few steps into a ring E diene, whose Diels-Alder reaction with phenyl vinyl sulfone and subsequent reductions has led to (+/-)-aspidofractinine. One-bond unraveling of a (phenylsulfonyl)aspidofractinine intermediate, followed by reductions, provided a second-generation pathway to (+/-)-aspidospermidine.

  DOI：

  10.1021/jo00104a023
• 作为产物：
  描述：

  (1S,12S,19R)-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,9-tetraene-11,17-dione 在 sodium tetrahydroborate 、 正丁基锂 、 cerium(III) chloride 、 三氟化硼乙醚 、 硫代乙氧基锂 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 正己烷 、 苯 为溶剂， 反应 213.42h， 生成 16,17-Didehydro-5-oxo-18-(phenylsulfonyl)aspidofractinine
  参考文献：
  名称：

  Total Synthesis of (.+-.)-Aspidofractinine and (.+-.)-Aspidospermidine

  摘要：

  Functional group manipulations on a previously constructed, easily accessible deethylaspidospermidine derivative have transformed the latter in few steps into a ring E diene, whose Diels-Alder reaction with phenyl vinyl sulfone and subsequent reductions has led to (+/-)-aspidofractinine. One-bond unraveling of a (phenylsulfonyl)aspidofractinine intermediate, followed by reductions, provided a second-generation pathway to (+/-)-aspidospermidine.

  DOI：

  10.1021/jo00104a023

文献信息

• Total Synthesis of (.+-.)-Aspidofractinine and (.+-.)-Aspidospermidine
  作者：Ernest Wenkert、Song Liu

  DOI：10.1021/jo00104a023

  日期：1994.12

  Functional group manipulations on a previously constructed, easily accessible deethylaspidospermidine derivative have transformed the latter in few steps into a ring E diene, whose Diels-Alder reaction with phenyl vinyl sulfone and subsequent reductions has led to (+/-)-aspidofractinine. One-bond unraveling of a (phenylsulfonyl)aspidofractinine intermediate, followed by reductions, provided a second-generation pathway to (+/-)-aspidospermidine.