N-((S)-3-methyl-1-(piperidin-1-yl)butan-2-yl)-N'-((S)-3-(methyl-1-(piperidin-1-yl)butan-2-yl)propan-2-yl)-P-phenylphosphonothioic diamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-((S)-3-methyl-1-(piperidin-1-yl)butan-2-yl)-N'-((S)-3-(methyl-1-(piperidin-1-yl)butan-2-yl)propan-2-yl)-P-phenylphosphonothioic diamide
• 化学式: C₂₆H₄₇N₄PS
• 分子量: 478.726
• InChiKey: VWGRRETWVCRNEC-CLJLJLNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  30.54
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (S)-Α-异丙基-1-哌啶乙胺 、 苯基硫代膦酰二氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到N-((S)-3-methyl-1-(piperidin-1-yl)butan-2-yl)-N'-((S)-3-(methyl-1-(piperidin-1-yl)butan-2-yl)propan-2-yl)-P-phenylphosphonothioic diamide
  参考文献：
  名称：

  Novel thiophosphonodiamides as efficient hydrogen bond donor catalysts in tandem Michael addition–cyclization of malononitrile and 2-(E)-2-nitrovinylphenols

  摘要：

  From L-amino acid, three chiral thiophosphonodiamides were prepared as new hydrogen bond donor organocatalysts. Under the mediation of the catalyst derived from L-valine, a tandem Michael addition/cyclization reaction between (E)-2-(2-nitrovinyl)phenols and malononitrile proceeds smoothly, giving pharmaceutically valuable 2-amino-4H-chromene-3-carbonitriles in high yields with 66-95% ee within 2 h. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.099
• 作为试剂：
  描述：

  反-2-羟基-β-硝基苯乙烯 、 丙二腈 在 N-((S)-3-methyl-1-(piperidin-1-yl)butan-2-yl)-N'-((S)-3-(methyl-1-(piperidin-1-yl)butan-2-yl)propan-2-yl)-P-phenylphosphonothioic diamide 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以84%的产率得到
  参考文献：
  名称：

  Novel thiophosphonodiamides as efficient hydrogen bond donor catalysts in tandem Michael addition–cyclization of malononitrile and 2-(E)-2-nitrovinylphenols

  摘要：

  From L-amino acid, three chiral thiophosphonodiamides were prepared as new hydrogen bond donor organocatalysts. Under the mediation of the catalyst derived from L-valine, a tandem Michael addition/cyclization reaction between (E)-2-(2-nitrovinyl)phenols and malononitrile proceeds smoothly, giving pharmaceutically valuable 2-amino-4H-chromene-3-carbonitriles in high yields with 66-95% ee within 2 h. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.099

文献信息

• Novel thiophosphonodiamides as efficient hydrogen bond donor catalysts in tandem Michael addition–cyclization of malononitrile and 2-(E)-2-nitrovinylphenols
  作者：Keling Hu、Youming Wang、Zhenghong Zhou、Chuchi Tang

  DOI：10.1016/j.tet.2013.11.099

  日期：2014.1

  From L-amino acid, three chiral thiophosphonodiamides were prepared as new hydrogen bond donor organocatalysts. Under the mediation of the catalyst derived from L-valine, a tandem Michael addition/cyclization reaction between (E)-2-(2-nitrovinyl)phenols and malononitrile proceeds smoothly, giving pharmaceutically valuable 2-amino-4H-chromene-3-carbonitriles in high yields with 66-95% ee within 2 h. (C) 2013 Elsevier Ltd. All rights reserved.