7-methoxy-3-phenylbenzo[d]isoxazole | 540751-00-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并异恶唑
• 英文名称: 7-methoxy-3-phenylbenzo[d]isoxazole
• 英文别名: 7-methoxy-3-phenylbenzisoxazole；7-methoxy-3-phenyl-benz[d]isoxazole；7-Methoxy-3-phenyl-benz[d]isoxazol；7-Methoxy-3-phenyl-1,2-benzoxazole
• CAS: 540751-00-6
• 化学式: C₁₄H₁₁NO₂
• 分子量: 225.247
• InChiKey: TYTQOEXSNWYMNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-methoxy-3-phenylbenzo[d]isoxazole 在 溴 、 溶剂黄146 作用下， 生成 4-bromo-7-methoxy-3-phenyl-benz[d]isoxazole
  参考文献：
  名称：

  Borsche; Hahn-Weinheimer, Justus Liebigs Annalen der Chemie, 1950, vol. 570, p. 155,159

  摘要：

  DOI：
• 作为产物：
  描述：

  2-hydroxy-3-methoxy-benzophenone oxime 、 乙酸酐 生成 7-methoxy-3-phenylbenzo[d]isoxazole
  参考文献：
  名称：

  Borsche; Hahn-Weinheimer, Justus Liebigs Annalen der Chemie, 1950, vol. 570, p. 155,159

  摘要：

  DOI：

文献信息

• A Novel PPh₃ Mediated One-Pot Method for Synthesis of 3-Aryl or Alkyl 1,2-Benzisoxazoles
  作者：GuiFang Chen、Hong Liu、ShuJia Li、Yu Tang、PeiYao Lu、KaiTian Xu、YuanMing Zhang

  DOI：10.1021/acs.orglett.7b00563

  日期：2017.4.7

  novel, efficient, and facile protocol has been developed for transforming 2-hydroxybenzonitriles and bromides into a range of 3-aryl or alkyl substituted 1,2-benzisoxazoles in good to excellent yields mediated by PPh3. The electronic and steric effects of bromides on the reaction are discussed. This is the first example to construct a C–C bond and heterocycle in a Barbier–Grignard-type reaction featuring

  已开发出新颖，有效且简便的方案，可以将PPh 3介导的2-羟基苄腈和溴化物以良好或优异的产率转化为一系列3-芳基或烷基取代的1,2-苯并恶唑。讨论了溴化物对反应的电子和空间效应。这是第一个在Barbier-Grignard型反应中构建C–C键和杂环的示例，该步骤的特征在于，比金属催化剂一步一步回收PPh 3更为容易。
• Benzisoxazole core and benzoxazolopyrrolidine via HDDA-derived benzyne with PTIO/DMPO
  作者：Yu Lei、Wenjing Zhu、Yajuan Zhang、Qiong Hu、Jie Dong、Yimin Hu

  DOI：10.1016/j.cclet.2022.107778

  日期：2023.4

  This research described a simple and efficient pathway for the synthesis of benzisoxazoles from arynes and PTIO (2-phenyl-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl), C−C and C−O bonds were formed in a single step without catalyst under mild conditions. The unexpected cleavage of C−N bond contributed to the formation of isoxazole ring, as indicated by DFT studies. Furthermore, we obtained the structure

  开发了一种通过硝酮捕获 HDDA 衍生苯炔的新方法。这项研究描述了一种从芳烃和 PTIO（2-苯基-4,4,5,5-四甲基咪唑啉-3-氧化物-1-氧基）、C−C 和 C−O 键合成苯并异恶唑的简单有效途径在温和条件下无需催化剂一步形成。如 DFT 研究所示，C-N 键的意外断裂有助于异恶唑环的形成。此外，当捕集剂为 DMPO（5,5-二甲基-1-吡咯啉N-氧化物）时，我们获得了苯并恶唑并吡咯烷的结构。
• Synthesis of Benzisoxazoles by the [3 + 2] Cycloaddition of <i>in situ</i> Generated Nitrile Oxides and Arynes
  作者：Anton V. Dubrovskiy、Richard C. Larock

  DOI：10.1021/ol902921s

  日期：2010.3.19

  A variety of substituted benzisoxazoles has been prepared by the [3 + 2] cycloaddition of nitrile oxides and arynes. Both components, being highly reactive Intermediates, have been generated In situ by fluoride anion from readily prepared aryne precursors and chlorooximes. The reaction scope is quite general, affording a novel, direct route to functionalized benzisoxazoles under mild reaction conditions.