(S)-(+)-1-chloro-3-(2-chlorophenylamino)-propan-2-ol | 1303526-27-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-(+)-1-chloro-3-(2-chlorophenylamino)-propan-2-ol
• 英文别名: (2S)-1-chloro-3-(2-chloroanilino)propan-2-ol
• CAS: 1303526-27-3
• 化学式: C₉H₁₁Cl₂NO
• 分子量: 220.098
• InChiKey: AMGNVVGTVUVMJO-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  邻氯苯胺 、 环氧氯丙烷 在 磷脂酶B 作用下， 以 异丙醚 为溶剂， 反应 12.0h， 生成 (S)-(+)-1-chloro-3-(2-chlorophenylamino)-propan-2-ol 、 (R)-1-chloro-3-(2-chlorophenylamino)-propan-2-ol
  参考文献：
  名称：

  Selective biocatalytic aminolysis of (±)-epichlorohydrin: Synthesis and ICAM-1 inhibitory activity of (S)-(+)-3-arylamino-1-chloropropan-2-ols

  摘要：

  Regio-and enantioselective synthesis of (S)-(+)-3-arylamino-1-chloropropan-2-ols has been achieved by the epoxide ring opening of (+/-)-epichlorohydrin with different aromatic amines in the presence of Candida rugosa lipase. Activities of seven model (S)-(+)-3-arylamino-1-chloropropan-2-ols, out of 10 compounds synthesized, have been evaluated for the inhibition of tumor necrosis factor-alpha TNF-alpha) induced expression of intercellular adhesion molecule-1 (ICAM-1), which is one of the factors responsible for the modulation of inflammation in biological systems; (S)-(+)-1-chloro-3-(2'-chlorophenylamino)-propan-2-ol has been found to exhibit highest activity, that is, 86% inhibition of TNF-alpha induced expression of ICAM-1 at a concentration of 40 mu g/ml. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.029