(S)-2-hydroxy-3-(p-chlorophenoxy)propylamine | 176700-45-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-2-hydroxy-3-(p-chlorophenoxy)propylamine
• 英文别名: 3-(4-chlorophenoxy)-2S-hydroxypropylamine；(-)-3-(4-chlorophenoxy)-2S-hydroxy-propylamine；(2S)-1-amino-3-(4-chlorophenoxy)propan-2-ol
• CAS: 176700-45-1
• 化学式: C₉H₁₂ClNO₂
• 分子量: 201.653
• InChiKey: WCTVXSRNGUMJKC-QMMMGPOBSA-N

物化性质

• 熔点：
  109-111 °C
• 沸点：
  363.7±32.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3,4-二氯苯基)-4-氧代丁酸 、 (S)-2-hydroxy-3-(p-chlorophenoxy)propylamine 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以24%的产率得到(2S,7aR)-2-(4-Chloro-phenoxymethyl)-7a-(3,4-dichloro-phenyl)-tetrahydro-pyrrolo[2,1-b]oxazol-5-one
  参考文献：
  名称：

  Substituted Tetrahydropyrrolo[2,1-b]oxazol-5(6H)-ones and Tetrahydropyrrolo[2,1-b]thiazol-5(6H)-ones as Hypoglycemic Agents

  摘要：

  A series of substituted tetrahydropyrrolo[2,1-b]oxazol-5(6H)-one and tetrahydropyrrolo[2,1-b]thiazol-5(6H)-ones was synthesized from amino alcohols or amino thiols and keto acids. A pharmacological model based on the results obtained with these compounds led to the synthesis and evaluation of a series of isoxazoles and other monocyclic compounds. These were evaluated for their ability to enhance glucose utilization in cultured L6 myocytes. The in vivo hypoglycemic efficacy and potency of these compounds were evaluated in a model of type 2 diabetes mellitus (non-insulin-dependent diabetes mellitus), the ob/ob mouse. 25a(2S) (SDZ PGU 693) was selected for further pharmacological studies.

  DOI：

  10.1021/jm9803121
• 作为产物：
  描述：

  对氯苯酚 在 sodium hydride 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 24.0h， 生成 (S)-2-hydroxy-3-(p-chlorophenoxy)propylamine
  参考文献：
  名称：

  A Convenient Synthesis of the Novel Hypoglycemic Agent SDZ PGU 693

  摘要：

  DOI：

  10.1021/jo010239d

文献信息

• Diastereomeric Resolution of Racemic<i>o</i>-Chloromandelic Acid
  作者：Pei Wang、En Zhang、Peng Zhao、Qing-Hua Ren、Yuan-Yuan Guan、Hong-Min Liu

  DOI：10.1002/chir.22089

  日期：2012.12

  The separation of rac‐o‐chloromandelic acid 1 with enantiopure aryloxypropylamine via diastereomeric salt formation was investigated. (R)‐o‐chloromandelic acid (R)‐1, a key intermediate for the antithrombotic agent clopidogrel, was obtained in 65% yield and 98% ee by Dutch resolution of rac‐1 with (S)‐2‐hydroxyl‐3‐(p‐chlorophenoxy) propylamine (S)‐5 as resolving agent and (S)‐2‐hydroxyl‐3‐(o‐nitrophenoxy)

  研究了通过非对映异构体盐的形成与对映体纯芳氧基丙胺分离外消旋-氯-扁桃酸1。（- [R ）- Ö -chloromandelic酸（[R - ）1以65％的收率和98％ee的得到由荷兰分辨率，抗血栓形成剂氯吡格雷的关键中间体，外消旋- 1与（小号）-2-羟基-3- -（对-氯苯氧基）丙胺（S）-5作为拆分剂，和（S）-2-羟基3-3-4 （邻硝基苯氧基）丙胺（S）-4作为成核抑制剂。手性24：1013–1017，2012年。分级为4 +©2012 Wiley Periodicals，Inc.
• Bicyclic oxazole and thiazole substituted ethers
  申请人：Novartis AG

  公开号：EP0702015B1

  公开（公告）日：1997-09-24
• Substituted Tetrahydropyrrolo[2,1-<i>b</i>]oxazol-5(6<i>H</i>)-ones and Tetrahydropyrrolo[2,1-<i>b</i>]thiazol-5(6<i>H</i>)-ones as Hypoglycemic Agents
  作者：Thomas D. Aicher、Bork Balkan、Philip A. Bell、Leonard J. Brand、S. H. Cheon、Rhonda O. Deems、Jay B. Fell、William S. Fillers、James D. Fraser、Jiaping Gao、Douglas C. Knorr、Gerald G. Kahle、Christina L. Leone、Jeffrey Nadelson、Ronald Simpson、Howard C. Smith

  DOI：10.1021/jm9803121

  日期：1998.11.1

  A series of substituted tetrahydropyrrolo[2,1-b]oxazol-5(6H)-one and tetrahydropyrrolo[2,1-b]thiazol-5(6H)-ones was synthesized from amino alcohols or amino thiols and keto acids. A pharmacological model based on the results obtained with these compounds led to the synthesis and evaluation of a series of isoxazoles and other monocyclic compounds. These were evaluated for their ability to enhance glucose utilization in cultured L6 myocytes. The in vivo hypoglycemic efficacy and potency of these compounds were evaluated in a model of type 2 diabetes mellitus (non-insulin-dependent diabetes mellitus), the ob/ob mouse. 25a(2S) (SDZ PGU 693) was selected for further pharmacological studies.
• A Convenient Synthesis of the Novel Hypoglycemic Agent SDZ PGU 693
  作者：Ranjit C. Desai

  DOI：10.1021/jo010239d

  日期：2001.7.1