(benzoylhydrazono)acetic acid isopropyl ester

• 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: (benzoylhydrazono)acetic acid isopropyl ester
• 英文别名: propan-2-yl (2E)-2-(benzoylhydrazinylidene)acetate
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: SUFJWBJPUMLDAS-MDWZMJQESA-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：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (benzoylhydrazono)acetic acid isopropyl ester 在 4-二甲氨基吡啶 、 simple strained silacycle chiral reagent 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 45.5h， 生成 (N'-benzoyl-N-tert-butoxycarbonylhydrazino)-(4-dimethyl-2-methoxyamniophenyl)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
• 作为产物：
  描述：

  L-(+)-酒石酸二异丙酯 在 sodium periodate 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 (benzoylhydrazono)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

• Stereospecific, Enantioselective Allylation of ?-Hydrazono Esters by Using Allyltrichlorosilanes with BINAP Dioxides as Neutral-Coordinate Organocatalysts
  作者：Chikako Ogawa、Masaharu Sugiura、Sh? Kobayashi

  DOI：10.1002/anie.200461312

  日期：2004.12.3
• WO2006/62901
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.