3-(4-methoxyphenyl)-5-((phenylselanyl)methyl)-4,5-dihydroisoxazole | 828939-56-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-methoxyphenyl)-5-((phenylselanyl)methyl)-4,5-dihydroisoxazole
• 英文别名: Isoxazole, 4,5-dihydro-3-(4-methoxyphenyl)-5-[(phenylseleno)methyl]-；3-(4-methoxyphenyl)-5-(phenylselanylmethyl)-4,5-dihydro-1,2-oxazole
• CAS: 828939-56-6
• 化学式: C₁₇H₁₇NO₂Se
• 分子量: 346.287
• InChiKey: OTRXMWKYFNNADD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-5-((phenylselanyl)methyl)-4,5-dihydroisoxazole 在 sodium iodide 、 碘甲烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Preparation of isoxazol(in)yl substituted selenides and their further deselenenylation reaction to synthesize 3,5-disubstituted isoxazoles

  摘要：

  We report a mild 1,3-dipolar cycloaddition protocol for the preparation of 3-aryl-5-phenylselenomethyl isoxazoles and isoxazolines regioselectively. The former was further reacted with LDA and electrophilic substrates followed by selenoxide syn-elimination to afford 3-aryl-5-E-substituted-ethenyl isoxazoles stereoselectively and the latter was subjected to a 'two-step' elimination to afford 3-aryl-5-methyl isoxazoles. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.071
• 作为产物：
  描述：

  对甲氧基苯甲醛肟 在 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 3-(4-methoxyphenyl)-5-((phenylselanyl)methyl)-4,5-dihydroisoxazole
  参考文献：
  名称：

  Preparation of isoxazol(in)yl substituted selenides and their further deselenenylation reaction to synthesize 3,5-disubstituted isoxazoles

  摘要：

  We report a mild 1,3-dipolar cycloaddition protocol for the preparation of 3-aryl-5-phenylselenomethyl isoxazoles and isoxazolines regioselectively. The former was further reacted with LDA and electrophilic substrates followed by selenoxide syn-elimination to afford 3-aryl-5-E-substituted-ethenyl isoxazoles stereoselectively and the latter was subjected to a 'two-step' elimination to afford 3-aryl-5-methyl isoxazoles. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.071

文献信息

• Electrochemical Chalcogenation of <i>β,γ</i> ‐Unsaturated Amides and Oximes to Corresponding Oxazolines and Isoxazolines
  作者：Samrat Mallick、Mrinmay Baidya、Kingshuk Mahanty、Debabrata Maiti、Suman De Sarkar

  DOI：10.1002/adsc.201901262

  日期：2020.3.4

  The current report represents a transition‐metal‐free synthesis of oxazoline and isoxazoline derivatives by a tandem electro‐oxidative chalcogenation‐cyclization process. Both C−Se and C−S bond‐forming protocols were developed without using any external oxidant and the reaction was performed at room temperature, open to the air. Using this methodology, 29 substituted oxazoline and 16 substituted isoxazoline

  本报告显示了通过串联电氧化硫属元素化-环化过程的无过渡金属合成恶唑啉和异恶唑啉衍生物。C-Se和C-S键形成方案均不使用任何外部氧化剂而开发，并且反应在室温下进行，并且对空气开放。使用这种方法，合成了29个取代的恶唑啉和16个取代的异恶唑啉衍生物，分离产率高达91％。
• Synthesis of Isoxazolines by the Electrophilic Chalcogenation of β,γ-Unsaturated Oximes: Fishing Novel Anti-Inflammatory Agents
  作者：Eric F. Lopes、Filipe Penteado、Samuel Thurow、Mikaela Pinz、Angelica S. Reis、Ethel A. Wilhelm、Cristiane Luchese、Thiago Barcellos、Bianca Dalberto、Diego Alves、Marcio S. da Silva、Eder J. Lenardão

  DOI：10.1021/acs.joc.9b01754

  日期：2019.10.4

  prepare chalcogen-functionalized isoxazolines. The strategy involves the reaction of β,γ-unsaturated oximes with electrophilic selenium and tellurium species, affording 19 new selenium- and tellurium-containing isoxazolines in good yields after 1 h at room temperature. The method was efficiently extended to the synthesis of 5 new (bis)isoxazoline ditellurides. One of the prepared compounds, 3-phenyl-5

  在这里，我们描述了一种制备硫族元素官能化的异恶唑啉的新策略。该策略涉及β，γ-不饱和肟与亲电子硒和碲物种的反应，在室温下放置1 h后，以良好的收率提供19种新的含硒和碲的异恶唑啉。该方法有效地扩展到5种新的（双）异恶唑啉二碲化物的合成。与参考药物塞来昔布相比，所制备的化合物之一3-苯基-5-（（苯基硒基）甲基）-异恶唑啉显示出更好的抗炎和抗水肿作用。
• Preparation of isoxazol(in)yl substituted selenides and their further deselenenylation reaction to synthesize 3,5-disubstituted isoxazoles
  作者：Wei Ming Xu、E. Tang、Xian Huang

  DOI：10.1016/j.tet.2004.10.071

  日期：2005.1

  We report a mild 1,3-dipolar cycloaddition protocol for the preparation of 3-aryl-5-phenylselenomethyl isoxazoles and isoxazolines regioselectively. The former was further reacted with LDA and electrophilic substrates followed by selenoxide syn-elimination to afford 3-aryl-5-E-substituted-ethenyl isoxazoles stereoselectively and the latter was subjected to a 'two-step' elimination to afford 3-aryl-5-methyl isoxazoles. (C) 2004 Elsevier Ltd. All rights reserved.