(-)-1-benzylidene-3-oxo-5-phenylpyrazolidin-1-ium-2-ide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (-)-1-benzylidene-3-oxo-5-phenylpyrazolidin-1-ium-2-ide
• 英文别名: (2Z)-2-benzylidene-3-phenyl-3,4-dihydropyrazol-2-ium-5-olate
• 化学式: C₁₆H₁₄N₂O
• 分子量: 250.3
• InChiKey: HXZWRXNYEMAPSJ-PDGQHHTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-1-benzylidene-3-oxo-5-phenylpyrazolidin-1-ium-2-ide 在 platinum(IV) oxide 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以92%的产率得到(S)-1-benzyl-5-phenylpyrazolidin-3-one
  参考文献：
  名称：

  Kinetic Resolutions of Azomethine Imines via Copper-Catalyzed [3 + 2] Cycloadditions

  摘要：

  An effective method has been developed for the kinetic resolution of racemic azomethine imines via [3 + 2] cycloadditions with alkynes catalyzed by a chiral copper complex. Efficient kinetic resolution is observed for a variety of N1 and C5 substituents on the dipole, thereby furnishing a wide array of useful enantioenriched azomethine imines, which can readily be transformed into monocyclic and bicyclic pyrazolidinones.

  DOI：

  10.1021/ja052876h
• 作为产物：
  描述：

  丙炔酸乙酯 、 2-benzylidene-5-oxo-3-phenylpyrazolidin-2-ium-1-ide 在 copper(l) iodide 、 (-)-phosphaferrocene-oxazoline 、 N-甲基二环己基胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以42%的产率得到(-)-1-benzylidene-3-oxo-5-phenylpyrazolidin-1-ium-2-ide
  参考文献：
  名称：

  Kinetic Resolutions of Azomethine Imines via Copper-Catalyzed [3 + 2] Cycloadditions

  摘要：

  An effective method has been developed for the kinetic resolution of racemic azomethine imines via [3 + 2] cycloadditions with alkynes catalyzed by a chiral copper complex. Efficient kinetic resolution is observed for a variety of N1 and C5 substituents on the dipole, thereby furnishing a wide array of useful enantioenriched azomethine imines, which can readily be transformed into monocyclic and bicyclic pyrazolidinones.

  DOI：

  10.1021/ja052876h

文献信息

• Kinetic Resolutions of Azomethine Imines via Copper-Catalyzed [3 + 2] Cycloadditions
  作者：Andrés Suárez、C. Wade Downey、Gregory C. Fu

  DOI：10.1021/ja052876h

  日期：2005.8.1

  An effective method has been developed for the kinetic resolution of racemic azomethine imines via [3 + 2] cycloadditions with alkynes catalyzed by a chiral copper complex. Efficient kinetic resolution is observed for a variety of N1 and C5 substituents on the dipole, thereby furnishing a wide array of useful enantioenriched azomethine imines, which can readily be transformed into monocyclic and bicyclic pyrazolidinones.