3-bromo-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione-18O | 1364232-89-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3-bromo-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione-18O
• CAS: 1364232-89-2
• 化学式: C₁₆H₁₂BrNO₂
• 分子量: 332.181
• InChiKey: XLBIHZGMIAHCBY-SPLUINJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  N-(4-methoxyphenyl)-N-methyl-3-phenylpropiolamide 在 N-溴代丁二酰亚胺(NBS) 、 重氧水 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以73%的产率得到3-bromo-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione-18O
  参考文献：
  名称：

  Intramolecular ipso-Halocyclization of 4-(p-Unsubstituted-aryl)-1-alkynes Leading to Spiro[4,5]trienones: Scope, Application, and Mechanistic Investigations

  摘要：

  A new, general method for the synthesis of spiro[4,5]trienores is described by the intramolecular ipso-halocyclization of 4-(p-unsubstituted-aryl)-1-alkynes. In the presence of halide electrophiles, a variety of 4-(p-unsubstituted-aryl)-1-alkynes underwent the intramolecular ipso-halocyclization with water smoothly, affording the corresponding halo-substituted spiro[4,5]trienones in moderate to good yields. The obtained spiro[4,5]trienones can be applied in constructing the azaquaternary tricyclic skeleton via Pd-catalyzed Heck reaction. Notably, the prepared spiro[4,5]trienones and azaquaternary tricycles are of importance in the areas of pharmaceuticals and agrochemicals. The mechanism of the intramolecular ipso-halocyclization reaction is also discussed according to the O-18-labeling experiments and DFT calculations.

  DOI：

  10.1021/jo300037n