(S)-(N'-benzoylhydrazino)-(4-pyrrolidin-1-yl-phenyl)acetic acid isopropyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-(N'-benzoylhydrazino)-(4-pyrrolidin-1-yl-phenyl)acetic acid isopropyl ester
• 英文别名: propan-2-yl (2S)-2-(2-benzoylhydrazinyl)-2-(4-pyrrolidin-1-ylphenyl)acetate
• 化学式: C₂₂H₂₇N₃O₃
• 分子量: 381.475
• InChiKey: XYAXETGSLODQTF-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  L-(+)-酒石酸二异丙酯 在 sodium periodate 、 simple strained silacycle chiral reagent 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 14.0h， 生成 (S)-(N'-benzoylhydrazino)-(4-pyrrolidin-1-yl-phenyl)acetic acid isopropyl ester
  参考文献：
  名称：

  Enantioselective Friedel−Crafts Alkylations with Benzoylhydrazones Promoted by a Simple Strained Silacycle Reagent

  摘要：

  The enantioselective Friedel-Crafts reaction of electron-rich arenes and heteroarenes with the benzoylhydrazone of isopropyl glyoxylate mediated by a simple chiral silane Lewis acid is described. The reactions are highly practical, as demonstrated by a larger scale (5 g of the hydrazone) reaction in which the recovery of the pseudoephedrine in 99% yield was achieved. A simple model is advanced to explain the observed enantioselectivity.

  DOI：

  10.1021/ja042522a

文献信息

• Enantioselective Friedel−Crafts Alkylations with Benzoylhydrazones Promoted by a Simple Strained Silacycle Reagent
  作者：Seiji Shirakawa、Richard Berger、James L. Leighton

  DOI：10.1021/ja042522a

  日期：2005.3.9

  The enantioselective Friedel-Crafts reaction of electron-rich arenes and heteroarenes with the benzoylhydrazone of isopropyl glyoxylate mediated by a simple chiral silane Lewis acid is described. The reactions are highly practical, as demonstrated by a larger scale (5 g of the hydrazone) reaction in which the recovery of the pseudoephedrine in 99% yield was achieved. A simple model is advanced to explain the observed enantioselectivity.