(1S,2R,2′S)-(-)-2-(2′-butylamino)-1-phenyl-1-propanol hydrochloride | 1615712-97-4

• 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: (1S,2R,2′S)-(-)-2-(2′-butylamino)-1-phenyl-1-propanol hydrochloride
• 英文别名: (1S,2R)-2-[[(2S)-butan-2-yl]amino]-1-phenylpropan-1-ol;hydrochloride
• CAS: 1615712-97-4
• 化学式: C₁₃H₂₁NO*ClH
• 分子量: 243.777
• InChiKey: SMXVOIFHRXWFMM-YFYDJDKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  32.3
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  左旋去甲麻黄碱 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 对甲苯磺酸 作用下， 以 异丙醇 、 甲苯 为溶剂， 110.0 ℃ 、344.75 kPa 条件下， 生成 (1S,2R,2′S)-(-)-2-(2′-butylamino)-1-phenyl-1-propanol hydrochloride
  参考文献：
  名称：

  Synthesis, antimicrobial and molecular docking studies of enantiomerically pure N-alkylated β-amino alcohols from phenylpropanolamines

  摘要：

  Enantiomerically pure N-alkylated beta-amino alcohols 1a, 1a', 1c, 1c', 1d, 1d', 1e and 1e', with ee 100% have been synthesized from phenylpropanolamines 2. Effect of the neighboring chiral environment on the newly formed chiral center has been studied experimentally and concluded that the newly formed chiral center's absolute configuration is opposite to the adjacent (alpha- or beta-) chiral environment. The antimicrobial activity of the synthesized beta-amino alcohols were screened using in vitro disc diffusion method and variable antimicrobial activities were shown for 1a, 1a', 1c, 1c', 1d, 1d', 1e & 1e' and amongst them 1d & 1d' exhibited significant activity against bacteria and fungi. In silico studies revealed all the synthesized beta-amino alcohols 1a-e and 1a'-e' have shown good binding energies ranging from -7.38 to -6.09 kJ/mol towards the target receptor DNA topoisomerase IV and 1d' has shown maximum binding energy -7.38 kJ/mol. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.027

文献信息

• Synthesis, antimicrobial and molecular docking studies of enantiomerically pure N-alkylated β-amino alcohols from phenylpropanolamines
  作者：K. Chennakesava Rao、Y. Arun、K. Easwaramoorthi、C. Balachandran、T. Prakasam、T. Eswara Yuvaraj、P.T. Perumal

  DOI：10.1016/j.bmcl.2014.05.027

  日期：2014.7

  Enantiomerically pure N-alkylated beta-amino alcohols 1a, 1a', 1c, 1c', 1d, 1d', 1e and 1e', with ee 100% have been synthesized from phenylpropanolamines 2. Effect of the neighboring chiral environment on the newly formed chiral center has been studied experimentally and concluded that the newly formed chiral center's absolute configuration is opposite to the adjacent (alpha- or beta-) chiral environment. The antimicrobial activity of the synthesized beta-amino alcohols were screened using in vitro disc diffusion method and variable antimicrobial activities were shown for 1a, 1a', 1c, 1c', 1d, 1d', 1e & 1e' and amongst them 1d & 1d' exhibited significant activity against bacteria and fungi. In silico studies revealed all the synthesized beta-amino alcohols 1a-e and 1a'-e' have shown good binding energies ranging from -7.38 to -6.09 kJ/mol towards the target receptor DNA topoisomerase IV and 1d' has shown maximum binding energy -7.38 kJ/mol. (C) 2014 Elsevier Ltd. All rights reserved.