(Rs)-N-((3aR,5S)-1-butyl-2-oxo-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-5-yl)-2-methylpropane-2-sulfinamide | 1560811-95-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (Rs)-N-((3aR,5S)-1-butyl-2-oxo-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-5-yl)-2-methylpropane-2-sulfinamide
• CAS: 1560811-95-1
• 化学式: C₂₁H₂₉NO₂S
• 分子量: 359.533
• InChiKey: HBUILVQGOCCAPC-ASUVVQHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (Rs)-N-((3aR,5S)-1-butyl-2-oxo-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-5-yl)-2-methylpropane-2-sulfinamide 在 盐酸 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 0.75h， 以98%的产率得到(3aR,5S)-5-amino-1-butyl-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one hydrochloride
  参考文献：
  名称：

  Asymmetric Allylation/Pauson–Khand Reaction: A Simple Entry to Polycyclic Amines. Application to the Synthesis of Aminosteroid Analogues

  摘要：

  Asymmetric allylation of o-iodoarylsulfinylimines has been achieved in high diastereoselectivities. The thus-obtained o-iodoarylhomoallylic sulfinamides participate in a subsequent Sonogashira coupling followed by a diastereoselective intramolecular Pauson-Khand reaction. In this way, tricyclic amines showing a unique benzo-fused indenyl backbone were obtained. The methodology has been applied to the synthesis of amino steroid analogues.

  DOI：

  10.1021/ol500142c
• 作为产物：
  描述：

  dicobalt octacarbonyl 、 (Rs)-N-((S)-1-(2-(hex-1-yn-1-yl)phenyl)but-3-en-1-yl)-2-methylpropane-2-sulfinamide 在 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以73%的产率得到(Rs)-N-((3aR,5S)-1-butyl-2-oxo-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-5-yl)-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  Asymmetric Allylation/Pauson–Khand Reaction: A Simple Entry to Polycyclic Amines. Application to the Synthesis of Aminosteroid Analogues

  摘要：

  Asymmetric allylation of o-iodoarylsulfinylimines has been achieved in high diastereoselectivities. The thus-obtained o-iodoarylhomoallylic sulfinamides participate in a subsequent Sonogashira coupling followed by a diastereoselective intramolecular Pauson-Khand reaction. In this way, tricyclic amines showing a unique benzo-fused indenyl backbone were obtained. The methodology has been applied to the synthesis of amino steroid analogues.

  DOI：

  10.1021/ol500142c