2-chloro-1-(4'-methanesulfonamidophenyl)ethanol | 157023-58-0

• 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'-methanesulfonamidophenyl)ethanol
• 英文别名: N-{4-[(1R)-2-chloro-1-hydroxyethyl]phenyl}methanesulfonamide；N-[4-[(1R)-2-chloro-1-hydroxyethyl]phenyl]methanesulfonamide
• CAS: 157023-58-0
• 化学式: C₉H₁₂ClNO₃S
• mdl: MFCD09863637
• 分子量: 249.718
• InChiKey: UMJVCKLQCMEZSH-VIFPVBQESA-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：
  0.333
• 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：

  异丙胺 、 2-chloro-1-(4'-methanesulfonamidophenyl)ethanol 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 (R)-sotalol
  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 在 potassium phosphate buffer 、 乙醇脱氢酶(NADP) 葡萄糖 、 D-glucose dehydrogenase 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 水 为溶剂， 以89%的产率得到2-chloro-1-(4'-methanesulfonamidophenyl)ethanol
  参考文献：
  名称：

  重要药物组成部分的“绿色”合成：酶法获得对映体纯的α-氯醇

  摘要：

  筛选了三十一种重组酮还原酶，以减少六种α-氯酮（药学上有价值的α-氯醇的前体）的还原。发现了几种高活性和对映选择性的酮还原酶，并以制备规模证明了它们在合成这些α-氯醇的两种对映异构体中的应用。这为此类重要的药物构建基块提供了便捷的“绿色”通道。

  DOI：

  10.1016/j.tetasy.2005.08.037

文献信息

• anti-Prelog microbial reduction of aryl α-halomethyl or α-hydroxymethyl ketones with Geotrichum sp. 38
  作者：Zhi-Liang Wei、Zu-Yi Li、Guo-Qiang Lin

  DOI：10.1016/s0040-4020(98)00796-0

  日期：1998.10

  Reduction of aryl α-halomethyl ketones 5a-d and 7a-h and α-hydroxymethyl ketones 10a-b by Geotrichum sp. 38 affording mostly the anti-Prelog alcohols was reported and the stereoselectivities of the reductive products were discussed.

  芳基α-卤代甲基酮的还原图5a-d以及图7a-H和α羟基酮10A-B由白地霉属。报道了38种主要提供抗-Prelog醇的化合物，并讨论了还原产物的立体选择性。
• ‘Green’ synthesis of important pharmaceutical building blocks: enzymatic access to enantiomerically pure α-chloroalcohols
  作者：Dunming Zhu、Chandrani Mukherjee、Ling Hua

  DOI：10.1016/j.tetasy.2005.08.037

  日期：2005.10

  α-chloroketones, the precursors of pharmaceutically valuable α-chloroalcohols. Several highly active and enantioselective ketoreductases were found and their applications to the synthesis of both enantiomers of these α-chloroalcohols were demonstrated on a preparative scale. This offers a convenient, ‘green’ access to this type of important pharmaceutical building blocks.

  筛选了三十一种重组酮还原酶，以减少六种α-氯酮（药学上有价值的α-氯醇的前体）的还原。发现了几种高活性和对映选择性的酮还原酶，并以制备规模证明了它们在合成这些α-氯醇的两种对映异构体中的应用。这为此类重要的药物构建基块提供了便捷的“绿色”通道。
• 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.