5-(4-甲氧基苯氧基)戊酸 | 374565-57-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 5-(4-甲氧基苯氧基)戊酸
• 英文名称: 5-(4-methoxyphenoxy)pentanoic acid
• CAS: 374565-57-8
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: HFDHPEFKVYEQKK-UHFFFAOYSA-N

物化性质

• 沸点：
  397.7±22.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  5-(4-甲氧基苯氧基)戊酸 在 TEA 、 四氯化钛 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 34.25h， 生成 (3S,4R,4'S)-1-(4-methoxyphenyl)-3-[3-(4-methoxyphenoxy)prop-1-yl]-4-(1,2-dihydroxyethyl)azetidin-2-one
  参考文献：
  名称：

  Efficient Synthesis of an Enantiopure β-Lactam as an Advanced Precursor of Thrombin and Tryptase Inhibitors

  摘要：

  A new and efficient synthesis of a beta-lactam that is an advanced precursor of inhibitors of thrombin and tryptase is reported. The reaction sequence is based on the use of an inexpensive enantiomerically pure starting material and is designed to allow access to both enantiomers of the target molecules by epimerization of a side-product obtained along the synthesis. An improved procedure for the epimerization step that takes advantage of the use of a polymer-supported and recyclable phase-transfer catalyst is described.

  DOI：

  10.1021/jo020617u
• 作为产物：
  描述：

  1-(4-溴丁氧基)-4-甲氧基苯 在 sodium hydroxide 、 硫酸 、 双氧水 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 22.5h， 生成 5-(4-甲氧基苯氧基)戊酸
  参考文献：
  名称：

  Synthesis and characterisation of13C and15N isotopomers of a 1-acyl-7-nitroindoline

  摘要：

  本文描述了合成水溶性、光敏性的1-酰基-7-硝基吲哚5的同位素体的高效方法，其中酰基的羰基位置包含13C，或者硝基位置包含15N。通过红外差谱光谱学结合闪光光解技术验证了同位素的掺入。

  DOI：

  10.1002/jlcr.494

文献信息

• Design, synthesis and evaluation of oxazolopyridinone derivatives as quorum sensing inhibitors
  作者：Weijin Chen、Panpan Zhang、Ting Guo、Xiaotong Gu、Bingfang Bai、Shenyan Zhang、Xiaohong Chang、Yingmei Wang、Shutao Ma

  DOI：10.1016/j.bioorg.2022.106266

  日期：2023.1

  to develop new antibacterial drugs with novel mechanism of action. Here we designed and synthesized three series of benzoxazolone, oxazolopyridinone and 3-(2-hydroxyphenyl)hydantoin derivatives and evaluated their activity as novel quorum sensing (QS) inhibitors. We found that benzoxazolone and oxazolopyridinone derivatives had promising QS inhibitory activity in the minimum inhibitory concentration

  抗生素危机与多重耐药（MDR）病原体的出现有关，这导致了严重的细菌感染，给现代社会带来了巨大的负担。因此，迫切需要开发作用机制新颖的新型抗菌药物。在这里，我们设计并合成了三个系列的苯并恶唑酮、恶唑并吡啶酮和 3-(2-羟基苯基) 乙内酰脲衍生物，并评估了它们作为新型群体感应 (QS) 抑制剂的活性。我们发现苯并恶唑酮和恶唑并吡啶酮衍生物在最小抑制浓度、绿脓素和鼠李糖脂抑制试验中具有很有前途的 QS 抑制活性。特别是， 256 μg/mL 的A10和B20不仅抑制了 QS 调节的绿脓素的产生铜绿假单胞菌PAO1 分别降低 36.55% 和 46.90%，而且还显示出最强的鼠李糖脂抑制活性，IC 50值分别为 66.35 和 56.75 µg/mL。进一步的研究表明， 64 μg/mL 的B20抑制了 40% 的铜绿假单胞菌PAO1生物膜形成，并削弱了其集群运动。更重要的是，B20联合环丙沙星
• Design, Synthesis, and Biological Evaluation of 2-Phenoxyalkylhydrazide Benzoxazole Derivatives as Quorum Sensing Inhibitors with Strong Antibiofilm Effect
  作者：Panpan Zhang、Yangchun Ma、Yingmei Wang、Enhui Dong、Shutao Ma

  DOI：10.1021/acs.jmedchem.3c02379

  日期：2024.4.11

  antibacterial agents with novel mechanisms to treat infections caused by drug-resistant bacteria. In this paper, we designed and synthesized 2-phenoxyalkylhydrazide benzoxazole derivatives and evaluated their quorum sensing inhibition activity. Among them, 26c at a concentration of 102.4 μg/mL not only inhibited the production of pyocyanin and rhamnolipid by 45.6% and 38.3%, respectively, but also suppressed

  随着细菌对传统抗生素的耐药性问题日益严重，迫切需要具有新机制的新型抗菌药物来治疗耐药菌引起的感染。在本文中，我们设计并合成了2-苯氧基烷基酰肼苯并恶唑衍生物，并评估了其群体感应抑制活性。其中，浓度为102.4 μg/mL的26c不仅能分别抑制绿脓素和鼠李糖脂的产生45.6%和38.3%，而且浓度为32 μg/mL的26c还能抑制76.6%的生物膜产生。此外， 26c不会影响细菌生长，但在感染铜绿假单胞菌PAO1的小鼠模型中，它可以帮助环丙沙星有效消除活细菌。在靶向实验中， 26c能够以浓度依赖性方式抑制PAO1- lasB - gfp和PAO1- pqsA - gfp的荧光强度，表明该化合物作用于群体感应系统。总体而言， 26c作为具有强抗生物膜作用的群体感应抑制剂值得进一步研究。
• Synthesis and optical properties of two new PPV derivatives embedded on the surface of PbS nanocrystals
  作者：Piotr Piatkowski、Wojciech Gadomski、Pawel Przybylski、Bożena Ratajska-Gadomska

  DOI：10.1016/j.jphotochem.2010.07.022

  日期：2010.9

  In this work we present the optical characteristics of three PPV derivatives, pure and conjugated with PbS nanocrystals (NCs). Our results exhibit strong dependence of the fluorescence lifetime of the polymers on the PbS concentration. It appears that the fluorescence lifetimes increase with the PbS NCs concentration. This is a surprising result because the presence of the quantum dots, which create new nonradiative pathways, should cause a shortening of the exciton lifetime. The observed phenomenon indicates that the surface of the PbS NCs strongly affects the excited polymer, leading to the stabilization of the emerging exciton. (C) 2010 Elsevier B.V. All rights reserved.
• Synthesis and characterisation of13C and15N isotopomers of a 1-acyl-7-nitroindoline
  作者：John E. T. Corrie、Andreas Barth、George Papageorgiou

  DOI：10.1002/jlcr.494

  日期：2001.8

  Efficient methods are described for synthesis of isotopomers of the water-soluble, photolabile 1-acyl-7-nitroindoline 5 with either 13C in the carbonyl of the acyl substituent or 15N in the nitro group. The isotopic incorporations were verified by IR difference spectroscopy coupled with flash photolysis.

  本文描述了合成水溶性、光敏性的1-酰基-7-硝基吲哚5的同位素体的高效方法，其中酰基的羰基位置包含13C，或者硝基位置包含15N。通过红外差谱光谱学结合闪光光解技术验证了同位素的掺入。
• Efficient Synthesis of an Enantiopure β-Lactam as an Advanced Precursor of Thrombin and Tryptase Inhibitors
  作者：Rita Annunziata、Maurizio Benaglia、Mauro Cinquini、Franco Cozzi、Francesco Maggioni、Alessandra Puglisi

  DOI：10.1021/jo020617u

  日期：2003.4.1

  A new and efficient synthesis of a beta-lactam that is an advanced precursor of inhibitors of thrombin and tryptase is reported. The reaction sequence is based on the use of an inexpensive enantiomerically pure starting material and is designed to allow access to both enantiomers of the target molecules by epimerization of a side-product obtained along the synthesis. An improved procedure for the epimerization step that takes advantage of the use of a polymer-supported and recyclable phase-transfer catalyst is described.