diisopropyl(2-oxopiperidin-1-yl)phosphonate

• 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: diisopropyl(2-oxopiperidin-1-yl)phosphonate
• 英文别名: n-(diisopropoxyphosphoryl)piperidone；N-(diisopropoxyphosphoryl)piperidone；1-di(propan-2-yloxy)phosphorylpiperidin-2-one
• 化学式: C₁₁H₂₂NO₄P
• 分子量: 263.274
• InChiKey: SNAHPAFIOAYYKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  哌啶酮 、 亚磷酸二异丙酯 在 2,2'-联吡啶 、 copper diacetate 作用下， 以 甲苯 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 0.67h， 以92%的产率得到diisopropyl(2-oxopiperidin-1-yl)phosphonate
  参考文献：
  名称：

  Copper-Catalyzed Oxidative Cross-Coupling of H-Phosphonates and Amides to N-Acylphosphoramidates

  摘要：

  A simple combination of copper(II) acetate (Cu(OAc)(2)) and an appropriate base could promote oxidative cross-coupling of H-phosphonates and amides using air as a terminal oxidant. The substrate scope was broad with respect to both dialkyl H-phosphonates and nitrogen nucleophiles (including oxazolidinone, lactam, pyrrolidinone, urea, indole, and sulfonamide derivatives), giving the corresponding P-N coupling products in moderate to high yields.

  DOI：

  10.1021/ol303420g

文献信息

• Phosphorylation ofN-trimethylsilyllactams
  作者：A. B. Uryupin、I. A. Rakhov、V. A. Kolesova、P. V. Petrovskii、T. A. Mastryukova、M. I. Kabachnik

  DOI：10.1007/bf00697149

  日期：1994.9

  Treatment of N-trimethylsilyllactams with phosphoryl chlorides results in mixtures of products, whose formation can be explained by competition between N- and O-phosphorylation.
• Copper-Catalyzed Oxidative Cross-Coupling of <i>H</i>-Phosphonates and Amides to <i>N</i>-Acylphosphoramidates
  作者：Xiongjie Jin、Kazuya Yamaguchi、Noritaka Mizuno

  DOI：10.1021/ol303420g

  日期：2013.1.18

  A simple combination of copper(II) acetate (Cu(OAc)(2)) and an appropriate base could promote oxidative cross-coupling of H-phosphonates and amides using air as a terminal oxidant. The substrate scope was broad with respect to both dialkyl H-phosphonates and nitrogen nucleophiles (including oxazolidinone, lactam, pyrrolidinone, urea, indole, and sulfonamide derivatives), giving the corresponding P-N coupling products in moderate to high yields.