N-<(2S)-3-cyano-2-hydroxypropan-1-yl>phthalimide | 132203-23-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-<(2S)-3-cyano-2-hydroxypropan-1-yl>phthalimide
• 英文别名: (R)-N-(3-cyano-2-hydroxypropyl)phthalimide；(3R)-4-(1,3-dioxoisoindol-2-yl)-3-hydroxybutanenitrile
• CAS: 132203-23-7
• 化学式: C₁₂H₁₀N₂O₃
• 分子量: 230.223
• InChiKey: FFQXXXBBRKUSHT-MRVPVSSYSA-N

物化性质

• 沸点：
  483.0±35.0 °C(Predicted)
• 密度：
  1.400±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  81.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-<(2S)-3-cyano-2-hydroxypropan-1-yl>phthalimide 在 盐酸 、 Dowex 50 W x 2-100 resin 作用下， 反应 20.0h， 生成 (R)-(-)-4-氨基-3-羟基丁酸
  参考文献：
  名称：

  An efficient synthesis of (3R)-4-amino-3-hydroxy butyric acid (GABOB) via cyclic sulfite methodology

  摘要：

  The cyclic sulfite 6 prepared from enantiomerically pure N-[(2S)-2,3-dihydroxypropan-1-yl]phthalimide 2 derived from D-mannitol upon treatment with KCN in DMF afforded N-[(2S)-3-cyano-2-hydroxy propan-1-yl]phthalimide which was hydrolysed to furnish good yield of GABOB. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00299-6
• 作为产物：
  描述：

  利伐沙班杂质151 在 吡啶 、 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 N-<(2S)-3-cyano-2-hydroxypropan-1-yl>phthalimide
  参考文献：
  名称：

  An efficient synthesis of (3R)-4-amino-3-hydroxy butyric acid (GABOB) via cyclic sulfite methodology

  摘要：

  The cyclic sulfite 6 prepared from enantiomerically pure N-[(2S)-2,3-dihydroxypropan-1-yl]phthalimide 2 derived from D-mannitol upon treatment with KCN in DMF afforded N-[(2S)-3-cyano-2-hydroxy propan-1-yl]phthalimide which was hydrolysed to furnish good yield of GABOB. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00299-6

文献信息

• Enhanced enantioselectivity of an enzymatic reaction by the sulfur functional group. A simple preparation of optically active .beta.-hydroxy nitriles using a lipase
  作者：Toshiyuki Itoh、Yumiko Takagi、Shigenori Nishiyama

  DOI：10.1021/jo00004a033

  日期：1991.2

  The enantioselectivity of a lipase-catalyzed hydrolysis was improved by varying the acyl residue into the sulfur functional one, i.e. the beta-(phenylthio)- or beta-(methylthio)acetoxy group, from acetate or valerate to realize satisfactory resolution of beta-hydroxy nitriles using lipase P (Pseudomonas sp.).
• An efficient synthesis of (3R)-4-amino-3-hydroxy butyric acid (GABOB) via cyclic sulfite methodology
  作者：B.B. Lohray、A. Sekar Reddy、Vidya Bhushan

  DOI：10.1016/0957-4166(96)00299-6

  日期：1996.8

  The cyclic sulfite 6 prepared from enantiomerically pure N-[(2S)-2,3-dihydroxypropan-1-yl]phthalimide 2 derived from D-mannitol upon treatment with KCN in DMF afforded N-[(2S)-3-cyano-2-hydroxy propan-1-yl]phthalimide which was hydrolysed to furnish good yield of GABOB. Copyright (C) 1996 Elsevier Science Ltd