diethyl α-azido cyclohexylphosphonate | 186187-32-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl α-azido cyclohexylphosphonate
• 英文别名: 1-Azido-1-diethoxyphosphorylcyclohexane
• CAS: 186187-32-6
• 化学式: C₁₀H₂₀N₃O₃P
• 分子量: 261.261
• InChiKey: FKKKVVICPZZUOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl α-azido cyclohexylphosphonate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 3.0h， 以77%的产率得到diethyl 1-aminocyclohexylphosphonate
  参考文献：
  名称：

  A New and Efficient Synthesis of α-Amino Cycloalkyl-Phosphonic AcidsviaElectrophilic Azidation of Cycloalkylphosphonates

  摘要：

  alpha-Amino cyclobutyl-, cyclopentyl- and cyclohexylphosphonic acids (13) were efficiently prepared from the related unsubstituted cycloalkphosphonates (5), in three steps including electrophilic azidation of the corresponding lithiated carbanions, hydrogenation of the intermediate alpha-azido cycloalkyl-phosphonates (10) and acidic hydrolysis of the resulting alpha-amino cycloalkyl-phosphonates (12).

  DOI：

  10.1080/00397919608004650
• 作为产物：
  描述：

  Cyclohexyl-phosphonic acid diethyl ester 在 正丁基锂 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 4.5h， 生成 diethyl α-azido cyclohexylphosphonate
  参考文献：
  名称：

  A New and Efficient Synthesis of α-Amino Cycloalkyl-Phosphonic AcidsviaElectrophilic Azidation of Cycloalkylphosphonates

  摘要：

  alpha-Amino cyclobutyl-, cyclopentyl- and cyclohexylphosphonic acids (13) were efficiently prepared from the related unsubstituted cycloalkphosphonates (5), in three steps including electrophilic azidation of the corresponding lithiated carbanions, hydrogenation of the intermediate alpha-azido cycloalkyl-phosphonates (10) and acidic hydrolysis of the resulting alpha-amino cycloalkyl-phosphonates (12).

  DOI：

  10.1080/00397919608004650

文献信息

• A New and Efficient Synthesis of α-Amino Cycloalkyl-Phosphonic Acids<i>via</i>Electrophilic Azidation of Cycloalkylphosphonates
  作者：Catherine Guéguen、Elie About-Jaude、Noël Collignon、Philippe Savignac

  DOI：10.1080/00397919608004650

  日期：1996.11

  alpha-Amino cyclobutyl-, cyclopentyl- and cyclohexylphosphonic acids (13) were efficiently prepared from the related unsubstituted cycloalkphosphonates (5), in three steps including electrophilic azidation of the corresponding lithiated carbanions, hydrogenation of the intermediate alpha-azido cycloalkyl-phosphonates (10) and acidic hydrolysis of the resulting alpha-amino cycloalkyl-phosphonates (12).