1-(3-(4-methoxyphenyl)isoxazol-5-yl)ethanone | 37091-31-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(3-(4-methoxyphenyl)isoxazol-5-yl)ethanone
• 英文别名: 1-[3-(4-Methoxyphenyl)-1,2-oxazol-5-yl]ethanone；1-[3-(4-methoxyphenyl)-1,2-oxazol-5-yl]ethanone
• CAS: 37091-31-9
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: DVFODQKOTBINBW-UHFFFAOYSA-N

物化性质

• 熔点：
  122-123 °C
• 沸点：
  406.2±40.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3-(4-methoxyphenyl)isoxazol-5-yl)ethanone 在 溴 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以91%的产率得到2-bromo-1-(3-(4-methoxyphenyl)isoxazol-5-yl)ethanone
  参考文献：
  名称：

  Substituted N-Phenyl-5-(2-(phenylamino)thiazol-4-yl)isoxazole-3-carboxamides Are Valuable Antitubercular Candidates that Evade Innate Efflux Machinery

  摘要：

  Tuberculosis remains one of the deadliest infectious diseases in the world, and the increased number of multidrug-resistant and extremely drug-resistant strains is a significant reason for concern. This makes the discovery of novel antitubercular agents a cogent priority. We have previously addressed this need by reporting a series of substituted 2-aminothiazoles capable to inhibit the growth of actively replicating, nonreplicating persistent, and resistant Mycobacterium tuberculosis strains. Clues from the structureactivity relationships lining up the antitubercular activity were exploited for the rational design of improved analogues. Two compounds, namely N-phenyl-5-(2-(p-tolylamino)thiazol-4-yl)isoxazole-3-carboxamide 7a and N-(pyridin-2-yl)-5-(2-(p-tolylamino)thiazol-4-yl)isoxazole-3-carboxamide 8a, were found to show high inhibitory activity toward susceptible M. tuberculosis strains, with an MIC90 of 0.1250.25 mu g/mL (0.330.66 mu M) and 0.060.125 mu g/mL (0.160.32 mu M), respectively. Moreover, they maintained good activity also toward resistant strains, and they were selective over other bacterial species and eukaryotic cells, metabolically stable, and apparently not susceptible to the action of efflux pumps.

  DOI：

  10.1021/acs.jmedchem.7b00793
• 作为产物：
  描述：

  [(4-甲氧苯基)次甲基]氮烷氧化 在 吡啶 、 chromium(VI) oxide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 1-(3-(4-methoxyphenyl)isoxazol-5-yl)ethanone
  参考文献：
  名称：

  Synthesis and herbicidal activity of isoxazole-substituted 1-aminoethylphosphonates and 1-hydroxyethylphosphonates

  摘要：

  AbstractIsoxazole‐substituted 1‐aminoethyl‐ and 1‐hydroxyethyiphosphonates were synthesized by a multi‐step procedure and were screened for herbicidal activity against Lepidium sativum L. and Cucumis sativus L. All the synthesized compounds exhibited notable herbicidal activity.

  DOI：

  10.1002/ps.2780400204

文献信息

• Efficient Access to Isoxazoles from Alkenes
  作者：Ashton Hamme II、Jianping Xu

  DOI：10.1055/s-2008-1042906

  日期：2008.4

  The direct regioselective synthesis of 3,5-disubstituted isoxazoles was achieved in one reaction vessel through a sequence of reactions involving the net bromination of an electron-deficient alkene, in situ generation of a nitrile oxide, 1,3-dipolar cycloaddition, and loss of HBr from an intermediate 5,5-disubstituted bromoisoxazoline. This one-pot process enables the synthesis of 3,5-disubstituted

  3,5-二取代异恶唑的直接区域选择性合成是在一个反应​​容器中通过一系列反应实现的，包括缺电子烯烃的净溴化、腈氧化物的原位生成、1,3-偶极环加成和损失HBr 来自中间体 5,5-二取代溴异恶唑啉。这种一锅法可以直接从缺电子烯烃合成 3,5-二取代异恶唑，从而消除 1,1-二取代溴烯烃炔替代物的分离。
• Isoxazoles from 1,1-disubstituted bromoalkenes
  作者：Sureshbabu Dadiboyena、Jianping Xu、Ashton T. Hamme

  DOI：10.1016/j.tetlet.2006.12.005

  日期：2007.2

  The regioselective synthesis of 3,5-disubstituted isoxazoles was achieved through the 1,3-dipolar cycloaddition of nitrile oxides with 1,1-disubstituted bromoalkenes. The substituted bromoalkenes function as alkyne synthons which were used to construct 5,5-disubstituted bromoisoxazoline intermediates that aromatize to the analogous isoxazoles through the loss of HBr.

  3,5-二取代异恶唑的区域选择性合成是通过腈氧化物与 1,1-二取代溴烯烃的 1,3-偶极环加成实现的。取代的溴烯烃用作炔合成子，用于构建 5,5-二取代的溴异恶唑啉中间体，通过失去 HBr 芳构化为类似的异恶唑。
• [3 + 2] Cycloaddition of nitrile oxides to dichloropropenes and 1,3‐dichlorobut‐2‐ene: A regioselectivity issue
  作者：Alexandra N. Shilova、Nina S. Shatokhina、Evgeniy V. Kondrashov

  DOI：10.1002/jhet.4787

  日期：2024.4

  The reaction of nitrile oxides with 2,3-dichloroprop-1-ene, 1,3-dichloroprop-1-ene, and 1,3-dichlorobut-2-ene leads to 5-(chloromethyl)isoxazoles, 4-(chloromethyl)isoxazoles, or to mixtures of both regioisomers. The direction of cycloaddition and reactivity of substrate is determined by the steric hindrance at the terminal carbon atom of the alkene double bond. It has been found that the isomeric products

  氧化腈与 2,3-二氯丙-1-烯、1,3-二氯丙-1-烯和 1,3-二氯丁-2-烯反应生成 5-(氯甲基)异恶唑、4-(氯甲基)异恶唑，或两种区域异构体的混合物。环加成的方向和底物的反应性由烯烃双键末端碳原子的空间位阻决定。研究发现，氧化腈与1,3-二氯丙烯环加成的异构产物具有显着不同的脱氯化氢能力。环加成的区域选择性和底物相对反应性的实验数据与量子化学计算的结果一致。