3-(4-chlorophenyl)-5-phenylselenomethylisoxazole | 833462-33-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-chlorophenyl)-5-phenylselenomethylisoxazole
• 英文别名: Isoxazole, 3-(4-chlorophenyl)-5-[(phenylseleno)methyl]-；3-(4-chlorophenyl)-5-(phenylselanylmethyl)-1,2-oxazole
• CAS: 833462-33-2
• 化学式: C₁₆H₁₂ClNOSe
• 分子量: 348.69
• InChiKey: MQMSZYBFAVVKMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-5-phenylselenomethylisoxazole 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-chloro-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
• 作为产物：
  描述：

  4-chlorobenzaldoxime 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-chlorophenyl)-5-phenylselenomethylisoxazole
  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