2-deoxy-2-(1-hydroxyeth-2-yl)amino-glycerol | 15294-89-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-deoxy-2-(1-hydroxyeth-2-yl)amino-glycerol
• 英文别名: 2-Hydroxyethyl-1,3-dihydroxy-2-propylamin；1,3-dihydroxy-2-(2'-hydroxyethyl)-amino-propane；2-(2-Hydroxyethylamino)propane-1,3-diol
• CAS: 15294-89-0
• 化学式: C₅H₁₃NO₃
• 分子量: 135.163
• InChiKey: BBDPCGFBRYRHQN-UHFFFAOYSA-N

物化性质

• 沸点：
  333.7±27.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-deoxy-2-(1-hydroxyeth-2-yl)amino-glycerol 在 氯化亚砜 作用下， 生成 2-Chlorethyl-1,3-dichlor-2-propylamin
  参考文献：
  名称：

  Synthesis of Potential Anticancer Agents

  摘要：

  DOI：

  10.1021/jm00315a061
• 作为产物：
  描述：

  1,3-di-O-benzyl-2-deoxy-2-(1-hydroxyeth-2-yl)amino-glycerol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以33%的产率得到2-deoxy-2-(1-hydroxyeth-2-yl)amino-glycerol
  参考文献：
  名称：

  Acyclic analogues of glucosamidine, 1-deoxynojirimycin and N-(1,3-dihydroxyprop-2-yl) derivative of valiolamine as potential glucosidase inhibitors

  摘要：

  The N-(beta-hydroxyethyl)acetamidine (4) was prepared. Mesylation of 8 gave the 1,3-di-O-benzyl-2-O-methanesulfonylglycerol (9). Nucleophilic displacement of the mesyloxy group in 9 with ethanolamine and morpholine gave 11 and 12, respectively. Their catalytic hydrogenation gave 2-deoxy-2-(1-hydroxyeth-2-yl)amino-glycerol (5) and 2-deoxy-2-(morpholin-4-yl)glycerol (13). The inhibition of the beta-D-glucosidase enzyme from sweet almond by 4, 5 and 13-16 has been studied. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00031-9

文献信息

• Process for the preparation of serinol and of serinol derivatives, and
  申请人：Eprova Aktiengesellschaft

  公开号：US04503252A1

  公开（公告）日：1985-03-05

  A method for the synthesis of serinol and serinol derivatives substituted at the nitrogen atoms by reacting a lower 1,3-dialkoxy-isopropyl halide with ammonia or an amine to form a 1,3-dialkoxy-isopropylamine and then removing the ether groups by heating with a hydrogen halide acid. The method allows the production of serinol and serinol derivatives using inexpensive starting materials in a simple manner and obtaining a high purity product which is free of interfering isomers. Novel compounds obtained by the method which are useful as pharmaceutical intermediates, X-ray contrasting agents and cytostatic or psychopharmacological drugs are also disclosed.

  一种合成丝氨醇和丝氨醇衍生物的方法，通过将低碳1,3-二烷氧基异丙基卤化物与氨或胺反应，形成1,3-二烷氧基异丙胺，然后通过与氢卤酸加热去除醚基团。该方法允许使用廉价起始材料以简单方式生产丝氨醇和丝氨醇衍生物，并获得高纯度产品，不含干扰异构体。该方法获得的新化合物可用作制药中间体、X射线造影剂和抗细胞增殖或精神药物。
• Acyclic analogues of glucosamidine, 1-deoxynojirimycin and N-(1,3-dihydroxyprop-2-yl) derivative of valiolamine as potential glucosidase inhibitors
  作者：El Sayed H. El Ashry、Adel A.-H. Abdel-Rahman、Yeldez El Kilany、Richard R. Schmidt

  DOI：10.1016/s0040-4020(99)00031-9

  日期：1999.2

  The N-(beta-hydroxyethyl)acetamidine (4) was prepared. Mesylation of 8 gave the 1,3-di-O-benzyl-2-O-methanesulfonylglycerol (9). Nucleophilic displacement of the mesyloxy group in 9 with ethanolamine and morpholine gave 11 and 12, respectively. Their catalytic hydrogenation gave 2-deoxy-2-(1-hydroxyeth-2-yl)amino-glycerol (5) and 2-deoxy-2-(morpholin-4-yl)glycerol (13). The inhibition of the beta-D-glucosidase enzyme from sweet almond by 4, 5 and 13-16 has been studied. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• Synthesis of Potential Anticancer Agents
  作者：Charles E. Williamson、Thomas J. Sayers、Arnold M. Seligman、Benjamin. Witten

  DOI：10.1021/jm00315a061

  日期：1967.5