3-(4-Methoxy-phenyl)-5-phenylselanylmethyl-isoxazole | 833462-42-3

• 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-Methoxy-phenyl)-5-phenylselanylmethyl-isoxazole
• 英文别名: 3-(4-Methoxyphenyl)-5-[(phenylselanyl)methyl]-1,2-oxazole；3-(4-methoxyphenyl)-5-(phenylselanylmethyl)-1,2-oxazole
• CAS: 833462-42-3
• 化学式: C₁₇H₁₅NO₂Se
• 分子量: 344.272
• InChiKey: WFTLZCUNYWIEDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  3-(4-Methoxy-phenyl)-5-phenylselanylmethyl-isoxazole 在 双氧水 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 2.83h， 生成 3-(4-methoxyl-phenyl)-5-(E-1,3-butadienyl)isoxazole
  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

• 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.