[1-(hydroxyimino)butyl]-phosphonic acid, diethyl ester | 73790-29-1

• 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: [1-(hydroxyimino)butyl]-phosphonic acid, diethyl ester
• 英文别名: α-Hydroxyimino-butyl-phosphonsaeure-diaethylester-；N-(1-diethoxyphosphorylbutylidene)hydroxylamine
• CAS: 73790-29-1
• 化学式: C₈H₁₈NO₄P
• 分子量: 223.209
• InChiKey: XXBXWURGRWICPK-UHFFFAOYSA-N

物化性质

• 沸点：
  298.9±23.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  68.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [1-(hydroxyimino)butyl]-phosphonic acid, diethyl ester 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 diethyl 1-nitrobutylphosphonate
  参考文献：
  名称：

  Enantioselective Synthesis of Quaternary α-Aminophosphonates via Conjugate Addition of α-Nitrophosphonates to Enones

  摘要：

  Enantioselective Michael addition of alpha-nitrophosphonates to enones for the synthesis of alpha-aminophosphonates is reported for the first time. The reaction proceeds in good to high yields and moderate to high selectivity in the presence of a new quinine thiourea catalyst. The quaternary nitrophosphonates were conveniently transformed to cyclic quaternary alpha-aminophosphonates via in situ reduction intramolecular cyclization or Baeyer-Villiger oxidation followed by in situ reduction intramolecular cyclization.

  DOI：

  10.1021/ol203132h
• 作为产物：
  描述：

  Butyryl-phosphonsaeure-diaethylester 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 [1-(hydroxyimino)butyl]-phosphonic acid, diethyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of Quaternary α-Aminophosphonates via Conjugate Addition of α-Nitrophosphonates to Enones

  摘要：

  Enantioselective Michael addition of alpha-nitrophosphonates to enones for the synthesis of alpha-aminophosphonates is reported for the first time. The reaction proceeds in good to high yields and moderate to high selectivity in the presence of a new quinine thiourea catalyst. The quaternary nitrophosphonates were conveniently transformed to cyclic quaternary alpha-aminophosphonates via in situ reduction intramolecular cyclization or Baeyer-Villiger oxidation followed by in situ reduction intramolecular cyclization.

  DOI：

  10.1021/ol203132h

文献信息

• Substrate Related<i>O,O</i>-Dialkyldipeptidylaminophosphonates, A New Type of Thrombin Inhibitor
  作者：Donovan Green、Geeta Patel、Said Elgendy、Jehan A. Baban、Emmanuel Skordalakes、Wahid Husman、Christopher A. Goodwin、Michael F. Scully、Vijay V. Kakkar、John Deadman

  DOI：10.1080/10426509608545208

  日期：1996.1
• Enantioselective Synthesis of Quaternary α-Aminophosphonates via Conjugate Addition of α-Nitrophosphonates to Enones
  作者：Kalisankar Bera、Irishi N. N. Namboothiri

  DOI：10.1021/ol203132h

  日期：2012.2.17

  Enantioselective Michael addition of alpha-nitrophosphonates to enones for the synthesis of alpha-aminophosphonates is reported for the first time. The reaction proceeds in good to high yields and moderate to high selectivity in the presence of a new quinine thiourea catalyst. The quaternary nitrophosphonates were conveniently transformed to cyclic quaternary alpha-aminophosphonates via in situ reduction intramolecular cyclization or Baeyer-Villiger oxidation followed by in situ reduction intramolecular cyclization.