(S)-1-(10-ethyl-10H-phenothiazin-1-yl)ethanol | 1321602-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: (S)-1-(10-ethyl-10H-phenothiazin-1-yl)ethanol
• 英文别名: (1S)-1-(10-ethylphenothiazin-1-yl)ethanol
• CAS: 1321602-39-4
• 化学式: C₁₆H₁₇NOS
• 分子量: 271.383
• InChiKey: RXVABEPLNZOHQY-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  48.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  10-Ethyl-10H-phenothiazinylcarboxaldehyde 在 lipase A from candida antarctica 、 magnesium 作用下， 以 乙醚 为溶剂， 反应 14.0h， 生成 (S)-1-(10-ethyl-10H-phenothiazin-1-yl)ethanol 、 (R)-1-(10-ethyl-10H-phenothiazin-1-yl)ethanol 、 (R)-1-(10-ethyl-10H-phenothiazin-1-yl)ethyl acetate
  参考文献：
  名称：

  Lipase-catalyzed kinetic resolutions of racemic 1-(10-ethyl-10H-phenothiazin-1,2, and 4-yl)ethanols and their acetates

  摘要：

  The synthesis of both enantiomers of 1-(10-ethyl-10H-phenothiazin-1,2, and 4-yl)ethanols 1a-c and their acetates via enantioselective methanolysis of the corresponding racemic esters rac 2a-c with lipase B from Candida antarctica (CaL-B) or/and by acylation of the racemic alcohols with the lipase A or lipase B from C antarctica (CaL-A and CaL-B) is described. The absolute configuration of enantiopure 1-(10-ethyl-10H-phenothiazin-1-yl)ethyl acetate 2a was assigned as (R) by using QM/MM(hf/3-21g:uff) calculations within the CaL-B (1LBT crystal structure) enzymic environment. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.05.009

文献信息

• Lipase-catalyzed kinetic resolutions of racemic 1-(10-ethyl-10H-phenothiazin-1,2, and 4-yl)ethanols and their acetates
  作者：Jürgen Brem、Sarolta Pilbák、Csaba Paizs、Gergely Bánóczi、Florin-Dan Irimie、Monica-Ioana Toşa、László Poppe

  DOI：10.1016/j.tetasy.2011.05.009

  日期：2011.4

  The synthesis of both enantiomers of 1-(10-ethyl-10H-phenothiazin-1,2, and 4-yl)ethanols 1a-c and their acetates via enantioselective methanolysis of the corresponding racemic esters rac 2a-c with lipase B from Candida antarctica (CaL-B) or/and by acylation of the racemic alcohols with the lipase A or lipase B from C antarctica (CaL-A and CaL-B) is described. The absolute configuration of enantiopure 1-(10-ethyl-10H-phenothiazin-1-yl)ethyl acetate 2a was assigned as (R) by using QM/MM(hf/3-21g:uff) calculations within the CaL-B (1LBT crystal structure) enzymic environment. (C) 2011 Elsevier Ltd. All rights reserved.