(+)-2-chloro-1-(4'-N-mesylaminophenyl)ethanol | 124486-72-2

• 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: (+)-2-chloro-1-(4'-N-mesylaminophenyl)ethanol
• 英文别名: N-[4-(2-chloro-1-hydroxyethyl)phenyl]methanesulfonamide
• CAS: 124486-72-2
• 化学式: C₉H₁₂ClNO₃S
• 分子量: 249.718
• InChiKey: UMJVCKLQCMEZSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 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：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-2-chloro-1-(4'-N-mesylaminophenyl)ethanol 在 Pseudomonas cepacia lipase 、 potassium carbonate 作用下， 以 甲醇 、 异丙醚 为溶剂， 反应 12.0h， 生成 右索他洛尔
  参考文献：
  名称：

  Chemoenzymatic synthesis of (S) and (R)-propranolol and sotalol employing one-pot lipase resolution protocol

  摘要：

  Synthesis of both enantiomers of biologically active propranolol and sotalol has been achieved in high optical purity by one-pot reduction of 3 and 7 followed by in situ lipase resolution of the respective chlorohydrins. Pseudomonas cepacia lipase immobilized on ceramic particles (PS-C) provided the chlorohydrin and acetate, which on nucleophilic substitution with isopropyl amine afforded the target amino alcohols in high enantio selectivity under mild reaction conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.084
• 作为产物：
  描述：

  N-[4-(2-氯乙酰基)苯基]甲磺酰胺 以80.4%的产率得到(+)-2-chloro-1-(4'-N-mesylaminophenyl)ethanol
  参考文献：
  名称：

  EP1346972

  摘要：

  公开号：

文献信息

• PROCESS FOR PRODUCING OPTICALLY ACTIVE HALOHYDRIN COMPOUND
  申请人：Ajinomoto Co., Inc.

  公开号：EP1346972A1

  公开（公告）日：2003-09-24

  A process of preparing an optically active halohydrin compound characterized by comprising asymmetric hydrogen transfer reduction of an α-haloketone compound in the presence of a group 9 transition metal compound having a substituted or unsubstituted cyclopentadienyl group and an optically active diamine compound. The asymmetric hydrogen transfer reduction is preferably conducted in the presence of a base.

  一种制备光学活性卤代化合物的工艺，其特征在于包括在具有取代或未取代环戊二烯基团的第9族过渡金属化合物和光学活性二胺化合物存在下，对α-卤代酮化合物进行不对称氢转移还原。不对称氢转移还原最好在碱存在下进行。
• EP1346972
  申请人：——

  公开号：——

  公开（公告）日：——
• US6888012B2
  申请人：——

  公开号：US6888012B2

  公开（公告）日：2005-05-03
• Chemoenzymatic synthesis of (S) and (R)-propranolol and sotalol employing one-pot lipase resolution protocol
  作者：Ahmed Kamal、Mahendra Sandbhor、Ahmad Ali Shaik

  DOI：10.1016/j.bmcl.2004.05.084

  日期：2004.9

  Synthesis of both enantiomers of biologically active propranolol and sotalol has been achieved in high optical purity by one-pot reduction of 3 and 7 followed by in situ lipase resolution of the respective chlorohydrins. Pseudomonas cepacia lipase immobilized on ceramic particles (PS-C) provided the chlorohydrin and acetate, which on nucleophilic substitution with isopropyl amine afforded the target amino alcohols in high enantio selectivity under mild reaction conditions. (C) 2004 Elsevier Ltd. All rights reserved.