(Rs)-2-methyl-N-((S)-1-(6-(phenylethynyl)benzo[d][1,3]dioxol-5-yl)but-3-en-1-yl)propane-2-sulfinamide | 1560811-27-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (Rs)-2-methyl-N-((S)-1-(6-(phenylethynyl)benzo[d][1,3]dioxol-5-yl)but-3-en-1-yl)propane-2-sulfinamide
• CAS: 1560811-27-9
• 化学式: C₂₃H₂₅NO₃S
• 分子量: 395.522
• InChiKey: ILDBSOWQICAINA-WTYVLRPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  dicobalt octacarbonyl 、 (Rs)-2-methyl-N-((S)-1-(6-(phenylethynyl)benzo[d][1,3]dioxol-5-yl)but-3-en-1-yl)propane-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75%的产率得到(Rs)-2-methyl-N-((3aR,5S)-2-oxo-1-phenyl-3,3a,4,5-tetrahydro-2H-cyclopenta[5,6]naphtho[2,3-d][1,3]dioxol-5-yl)propane-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
• 作为产物：
  描述：

  6-iodopiperonal 在 bis-triphenylphosphine-palladium(II) chloride 、 titanium(IV) tetraethanolate 、 copper(l) iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 三乙胺 为溶剂， 反应 21.0h， 生成 (Rs)-2-methyl-N-((S)-1-(6-(phenylethynyl)benzo[d][1,3]dioxol-5-yl)but-3-en-1-yl)propane-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