ethyl 5-(4-hydroxyphenoxy)pentanoate | 892861-29-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: ethyl 5-(4-hydroxyphenoxy)pentanoate
• CAS: 892861-29-9
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: GBJLVEJEQCXLGO-UHFFFAOYSA-N

物化性质

• 沸点：
  371.4±22.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 5-(4-hydroxyphenoxy)pentanoate 在 bis-triphenylphosphine-palladium(II) chloride 吡啶 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.33h， 生成 ethyl 5-[4-(1-benzofuran-2-yl)phenoxy]pentanoate
  参考文献：
  名称：

  Discovery of a new chemical lead for a matrix metalloproteinase inhibitor

  摘要：

  A series of N-benzoyl gamma-aminobutyric hydroxamic acids were synthesized and evaluated as matrix metalloproteinase inhibitors. First, we focused on chemical modification of the N-benzoyl residue. Introduction of electron-rich para-substituents was effective to increase the inhibitory activity. Especially, some of the analogs with relatively more planar N-acyl residues, such as 10 and 11, demonstrated more potent activity. Second, chemical modification of the gamma-aminobutyric hydroxamic acid moiety was carried out to optimize the three-dimensional arrangement of the two pharmacophores (hydroxamic acid and N-acyl residues). Among the tested, the gamma-aminobutyric hydroxamic acid moiety was found to be the best spacer for connecting the above-mentioned two pharmacophores. Synthesis and structure-activity relationships are discussed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.059
• 作为产物：
  描述：

  ethyl 5-[4-(benzyloxy)phenoxy]pentanoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以100%的产率得到ethyl 5-(4-hydroxyphenoxy)pentanoate
  参考文献：
  名称：

  Discovery of a new chemical lead for a matrix metalloproteinase inhibitor

  摘要：

  A series of N-benzoyl gamma-aminobutyric hydroxamic acids were synthesized and evaluated as matrix metalloproteinase inhibitors. First, we focused on chemical modification of the N-benzoyl residue. Introduction of electron-rich para-substituents was effective to increase the inhibitory activity. Especially, some of the analogs with relatively more planar N-acyl residues, such as 10 and 11, demonstrated more potent activity. Second, chemical modification of the gamma-aminobutyric hydroxamic acid moiety was carried out to optimize the three-dimensional arrangement of the two pharmacophores (hydroxamic acid and N-acyl residues). Among the tested, the gamma-aminobutyric hydroxamic acid moiety was found to be the best spacer for connecting the above-mentioned two pharmacophores. Synthesis and structure-activity relationships are discussed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.059

文献信息

• Supramolecular Enhancement of Charge Transport through Pillar[5]arene‐Based Self‐Assembled Monolayers
  作者：Xiaobing Li、Siyuan Zhou、Qi Zhao、Yi Chen、Pan Qi、Yongkang Zhang、Lu Wang、Cunlan Guo、Shigui Chen

  DOI：10.1002/anie.202216987

  日期：——

  transport at a molecular junction is realized in pillar[5]arene-based self-assembled monolayers through host–guest interactions with cationic guest molecules. The improved charge transport is positively correlated with the strong binding affinity between pillar[5]arene and cationic guest molecules, which results in a delocalized structure in the supramolecular complex and a reduced energy offset.

  通过主客体与阳离子客体分子的相互作用，在基于柱 [5] 芳烃的自组装单分子层中实现了分子连接处电荷传输的显着增强。改进的电荷传输与柱 [5] 芳烃和阳离子客体分子之间的强结合亲和力正相关，这导致超分子复合物中的离域结构和减少的能量偏移。