(R)-1-(4-bromophenyl)-2-(methoxymethoxy)ethanol | 1548043-70-4

• 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: (R)-1-(4-bromophenyl)-2-(methoxymethoxy)ethanol
• 英文别名: (1R)-1-(4-bromophenyl)-2-(methoxymethoxy)ethanol
• CAS: 1548043-70-4
• 化学式: C₁₀H₁₃BrO₃
• 分子量: 261.115
• InChiKey: WOCOYNIOMURNJZ-JTQLQIEISA-N

物化性质

• 沸点：
  339.5±32.0 °C(predicted)
• 密度：
  1.431±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-1-(4-bromophenyl)-2-(methoxymethoxy)ethanol 在 盐酸羟胺 、 sodium methylate 、 对甲苯磺酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 64.0h， 生成 (R)-2-[1-(4-bromophenyl)-2-hydroxyethoxy]-N-hydroxyacetamide
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular docking studies of benzyloxyacetohydroxamic acids as LpxC inhibitors

  摘要：

  The inhibition of the UDP-3-O-[(R)-3-hydroxymyristoyl]-N-acetylglucosamine deacetylase (LpxC) represents a promising strategy to combat infections caused by multidrug-resistant Gram-negative bacteria. In order to elucidate the functional groups being important for the inhibition of LpxC, the structure of our previously reported hydroxamic acid 4 should be systematically varied. Therefore, a series of benzyloxyacetohydroxamic acids was prepared, of which the diphenylacetylene derivatives 28 (K-i = 95 nM) and 21 (K-i = 66 nM) were the most potent inhibitors of Escherichia coli LpxC. These compounds could be synthesized in a stereoselective manner employing a Sharpless asymmetric dihydroxylation and a Sonogashira coupling in the key steps. The obtained structure-activity relationships could be rationalized by molecular docking studies. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.057
• 作为产物：
  描述：

  氯甲基甲基醚 、 (R)-1-(4-bromophenyl)ethane-1,2-diol 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以46%的产率得到(R)-1-(4-bromophenyl)-2-(methoxymethoxy)ethanol
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular docking studies of benzyloxyacetohydroxamic acids as LpxC inhibitors

  摘要：

  The inhibition of the UDP-3-O-[(R)-3-hydroxymyristoyl]-N-acetylglucosamine deacetylase (LpxC) represents a promising strategy to combat infections caused by multidrug-resistant Gram-negative bacteria. In order to elucidate the functional groups being important for the inhibition of LpxC, the structure of our previously reported hydroxamic acid 4 should be systematically varied. Therefore, a series of benzyloxyacetohydroxamic acids was prepared, of which the diphenylacetylene derivatives 28 (K-i = 95 nM) and 21 (K-i = 66 nM) were the most potent inhibitors of Escherichia coli LpxC. These compounds could be synthesized in a stereoselective manner employing a Sharpless asymmetric dihydroxylation and a Sonogashira coupling in the key steps. The obtained structure-activity relationships could be rationalized by molecular docking studies. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.057