(5S)-5-phenyl[1,4]dioxan-2-one | 302843-01-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (5S)-5-phenyl[1,4]dioxan-2-one
• 英文别名: (S)-5-phenyl-1,4-dioxan-2-one；(5S)-5-phenyl-1,4-dioxan-2-one
• CAS: 302843-01-2
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: ISMJDTGDJASKHW-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S)-5-phenyl[1,4]dioxan-2-one 在 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以36%的产率得到(S)-N-hydroxy-2-(2-hydroxy-1-phenylethoxy)acetamide
  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：

  (S)-phenylethyleneglycol 在 四丁基氟化铵 、 sodium hydride 、 三氟乙酸 作用下， 生成 (5S)-5-phenyl[1,4]dioxan-2-one
  参考文献：
  名称：

  Anti-Selective Glycolate Aldol Additions with an Oxapyrone Boron Enolate

  摘要：

  GRAPHICSThe boron enolate of pyrone 2 undergoes asymmetric aldol reactions with aldehydes to give protected anti 1,2 diols 3. The pyrone is readily available from trans stilbene using asymmetric dihydroxylation. Yields for the aldol reaction range from 62 to 92% and the selectivities from 6:1 to >20:1 for the anti isomers, Protection and hydrogenolysis of the products can be used to remove the pyrone, giving differentially protected diol intermediates 12 that are amenable to multistep synthesis.

  DOI：

  10.1021/ol0002166

文献信息

• Synthesis, biological evaluation and molecular docking studies of benzyloxyacetohydroxamic acids as LpxC inhibitors
  作者：Marina Szermerski、Jelena Melesina、Kanin Wichapong、Marius Löppenberg、Joachim Jose、Wolfgang Sippl、Ralph Holl

  DOI：10.1016/j.bmc.2013.12.057

  日期：2014.2

  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.
• <i>Anti</i>-Selective Glycolate Aldol Additions with an Oxapyrone Boron Enolate
  作者：Merritt B. Andrus、B. B. V. Soma Sekhar、Erik L. Meredith、N. Kent Dalley

  DOI：10.1021/ol0002166

  日期：2000.9.1

  GRAPHICSThe boron enolate of pyrone 2 undergoes asymmetric aldol reactions with aldehydes to give protected anti 1,2 diols 3. The pyrone is readily available from trans stilbene using asymmetric dihydroxylation. Yields for the aldol reaction range from 62 to 92% and the selectivities from 6:1 to >20:1 for the anti isomers, Protection and hydrogenolysis of the products can be used to remove the pyrone, giving differentially protected diol intermediates 12 that are amenable to multistep synthesis.