(S)-(N'-benzoylhydrazino)-(4-dimethylamino-2-methoxyphenyl)-acetic acid isopropyl ester | 849097-60-5

• 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: (S)-(N'-benzoylhydrazino)-(4-dimethylamino-2-methoxyphenyl)-acetic acid isopropyl ester
• 英文别名: propan-2-yl (2S)-2-(2-benzoylhydrazinyl)-2-[4-(dimethylamino)-2-methoxyphenyl]acetate
• CAS: 849097-60-5
• 化学式: C₂₁H₂₇N₃O₄
• 分子量: 385.463
• InChiKey: NPCNFNIOIWDLCO-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  79.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-(N'-benzoylhydrazino)-(4-dimethylamino-2-methoxyphenyl)-acetic acid isopropyl ester 在 甲醇 、 4-二甲氨基吡啶 、 samarium diiodide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 tert-butoxycarbonylamino-(4-dimethylamino-2-methoxyphenyl)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 、 simple strained silacycle chiral reagent 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 59.0h， 生成 (S)-(N'-benzoylhydrazino)-(4-dimethylamino-2-methoxyphenyl)-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

• WO2006/62901
  申请人：——

  公开号：——

  公开（公告）日：——