ethyl (2Z,5E)-2-hydroxy-4-oxo-6-phenylhexa-2,5-dienoate | 1203610-94-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: ethyl (2Z,5E)-2-hydroxy-4-oxo-6-phenylhexa-2,5-dienoate
• 英文别名: ethyl 5-(3-hydroxyphenyl)isoxazole-3-carboxylate；ethyl 5-(3-hydroxyphenyl)-1,2-oxazole-3-carboxylate
• CAS: 1203610-94-9
• 化学式: C₁₂H₁₁NO₄
• 分子量: 233.224
• InChiKey: BJTUFTHPXQPNRJ-UHFFFAOYSA-N

物化性质

• 沸点：
  454.7±40.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (2Z,5E)-2-hydroxy-4-oxo-6-phenylhexa-2,5-dienoate 以 乙腈 为溶剂， 以75%的产率得到ethyl 5-(3-hydroxyphenyl)oxazole-2-carboxylate
  参考文献：
  名称：

  将异恶唑转化为多种恶唑产物的连续流光异构化反应的发展。

  摘要：

  提出了一种连续流动的方法，其通过光化学转座反应将异恶唑直接转化为它们的恶唑对应物。这导致首次报道了利用这种转化来确定其范围和综合实用性的方法。通过这种快速而温和的流动过程，实现了一系列带有不同附件的包括不同杂环部分的各种二取代和三取代的恶唑产物。此外，通过生成克量的选定产品，同时还提供了对可能的中间体的见识，证明了这种方法的鲁棒性。

  DOI：

  10.1021/acs.joc.9b03399
• 作为产物：
  描述：

  5-[[(tert-butyldiphenyl)silanyloxy]phenyl]-3-isoxazolecarboxylic acid ethyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以67%的产率得到ethyl (2Z,5E)-2-hydroxy-4-oxo-6-phenylhexa-2,5-dienoate
  参考文献：
  名称：

  Rational Design of 5-Phenyl-3-isoxazolecarboxylic Acid Ethyl Esters as Growth Inhibitors of Mycobacterium tuberculosis. A Potent and Selective Series for Further Drug Development

  摘要：

  New antituberculosis (anti-TB) drugs are urgently needed to shorten the 6-12 month treatment regimen and especially to battle drug-resistant Mycobacterium tuberculosis (Mtb) strains. In this study, we have continued our efforts to develop isoxazole-based anti-TB compounds by applying rational drug design approach. The biological activity and the structure-activity relationships (SAR) for a designed series of 5-phenyl-3-isoxazolecarboxylic acid ethyl ester derived anti-TB compounds were investigated. Several compounds were found to exhibit nanomolar activity against the replicating bacteria (R-TB) and low micromolar activity against the nonreplicating bacteria (NRP-TB). The series showed excellent selectivity toward Mtb, and in general, no cytotoxicity was observed in Vero cells (IC50 > 128 mu M). Notably, selected compounds also retained their activity against isoniazid (INH), rifampin (RMP), and streptomycin (SM) resistant Mtb strains. Hence, benzyloxy, benzylamino, and phenoxy derivatives of 5-phenyl-3-isoxazolecarboxylic acid ethyl esters represent a highly potent, selective, and versatile series of anti-TB compounds and as Such present attractive lead compounds for further TB drug development.

  DOI：

  10.1021/jm901273n

文献信息

• Oxidize Amines to Nitrile Oxides: One Type of Amine Oxidation and Its Application to Directly Construct Isoxazoles and Isoxazolines
  作者：Xiao-Wei Zhang、Xiao-Lin He、Nan Yan、Hong-Xing Zheng、Xiang-Guo Hu

  DOI：10.1021/acs.joc.0c02281

  日期：2020.12.4

  A facile oxidative heterocyclization of commercially available amines and tert-butyl nitrite with alkynes or alkenes leading to isoxazoles or isoxazolines is described. The unprecedented strategy of the oxidation of an amine directly to a nitrile oxide was used in this cyclization process. This reaction is highly efficient, regiospecific, operationally simple, mild, and tolerant of a variety of functional

  描述了可商购的胺和亚硝酸叔丁酯与炔或烯烃的容易的氧化性杂环化，其导致异恶唑或异恶唑啉。在这种环化过程中使用了前所未有的将胺直接氧化为一氧化氮的策略。该反应是高效的，区域特异性的，操作简单的，温和的，并且耐受多种官能团。对照实验为这种新型的氧化环化反应提供了一种一氧化氮中间体机制。此外，实现了对生物活性分子骨架的合成应用和药物的后期修饰。
• Discovery of a Novel Potent and Selective HSD17B13 Inhibitor, BI-3231, a Well-Characterized Chemical Probe Available for Open Science
  作者：Sven Thamm、Marina K. Willwacher、Gary E. Aspnes、Tom Bretschneider、Nicholas F. Brown、Silke Buschbom-Helmke、Thomas Fox、Emanuele M. Gargano、Daniel Grabowski、Christoph Hoenke、Damian Matera、Katja Mueck、Stefan Peters、Sophia Reindl、Doris Riether、Matthias Schmid、Christofer S. Tautermann、Aaron M. Teitelbaum、Cornelius Trünkle、Thomas Veser、Martin Winter、Lars Wortmann

  DOI：10.1021/acs.jmedchem.2c01884

  日期：2023.2.23
• Development of a Continuous Flow Photoisomerization Reaction Converting Isoxazoles into Diverse Oxazole Products
  作者：Cormac Bracken、Marcus Baumann

  DOI：10.1021/acs.joc.9b03399

  日期：2020.2.21

  A continuous flow process is presented, which directly converts isoxazoles into their oxazole counterparts via a photochemical transposition reaction. This results in the first reported exploitation of this transformation to establish its scope and synthetic utility. A series of various di- and trisubstituted oxazole products bearing different appendages including different heterocyclic moieties were

  提出了一种连续流动的方法，其通过光化学转座反应将异恶唑直接转化为它们的恶唑对应物。这导致首次报道了利用这种转化来确定其范围和综合实用性的方法。通过这种快速而温和的流动过程，实现了一系列带有不同附件的包括不同杂环部分的各种二取代和三取代的恶唑产物。此外，通过生成克量的选定产品，同时还提供了对可能的中间体的见识，证明了这种方法的鲁棒性。
• Rational Design of 5-Phenyl-3-isoxazolecarboxylic Acid Ethyl Esters as Growth Inhibitors of <i>Mycobacterium tuberculosis</i>. A Potent and Selective Series for Further Drug Development
  作者：Annamaria Lilienkampf、Marco Pieroni、Baojie Wan、Yuehong Wang、Scott G. Franzblau、Alan P. Kozikowski

  DOI：10.1021/jm901273n

  日期：2010.1.28

  New antituberculosis (anti-TB) drugs are urgently needed to shorten the 6-12 month treatment regimen and especially to battle drug-resistant Mycobacterium tuberculosis (Mtb) strains. In this study, we have continued our efforts to develop isoxazole-based anti-TB compounds by applying rational drug design approach. The biological activity and the structure-activity relationships (SAR) for a designed series of 5-phenyl-3-isoxazolecarboxylic acid ethyl ester derived anti-TB compounds were investigated. Several compounds were found to exhibit nanomolar activity against the replicating bacteria (R-TB) and low micromolar activity against the nonreplicating bacteria (NRP-TB). The series showed excellent selectivity toward Mtb, and in general, no cytotoxicity was observed in Vero cells (IC50 > 128 mu M). Notably, selected compounds also retained their activity against isoniazid (INH), rifampin (RMP), and streptomycin (SM) resistant Mtb strains. Hence, benzyloxy, benzylamino, and phenoxy derivatives of 5-phenyl-3-isoxazolecarboxylic acid ethyl esters represent a highly potent, selective, and versatile series of anti-TB compounds and as Such present attractive lead compounds for further TB drug development.