3-bromo-1-(2-bromobenzyl)-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione | 1364232-49-4

• 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-bromo-1-(2-bromobenzyl)-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione
• 英文别名: 3-Bromo-1-[(2-bromophenyl)methyl]-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione
• CAS: 1364232-49-4
• 化学式: C₂₂H₁₅Br₂NO₂
• 分子量: 485.175
• InChiKey: DRHGIBMAWWITGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-1-(2-bromobenzyl)-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione 在 bis-triphenylphosphine-palladium(II) chloride 、 四丁基溴化铵 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 120.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 以71%的产率得到6-bromo-5-phenyl-1H-pyrrolo[2,1-e]phenanthridine-2,7(9H,13bH)-dione
  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
• 作为产物：
  描述：

  在 Oxone 、 水 、 zinc dibromide 作用下， 以 乙腈 为溶剂， 以81%的产率得到3-bromo-1-(2-bromobenzyl)-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione
  参考文献：
  名称：

  ZnBr 2介导的丙酰胺酰胺的氧化螺-溴环化反应，用于合成3-溴-1-azaspiro [4.5] deca-3,6,9-三烯-2,8-二酮†

  摘要：

  本文已经描述了ZnBr 2介导的N-芳基丙酰胺酰胺的氧化螺-溴环化，用于高效合成3-溴-1-氮杂螺[4.5] deca-3,6,9-三烯-2,8-二酮。将一当量的水引入到最终产品中。该反应在室温下有效地进行，并且显示出优异的官能团耐受性。在标准条件下，3-溴-1-氧杂螺[4.5] deca-3,6,9-三烯-2,8-二酮和3-溴-1-氮杂螺[4.5] deca-3,6,9-trien-合成了8个。

  DOI：

  10.1039/c7ob00293a

文献信息

• Intramolecular <i>ipso</i>-Halocyclization of 4-(<i>p</i>-Unsubstituted-aryl)-1-alkynes Leading to Spiro[4,5]trienones: Scope, Application, and Mechanistic Investigations
  作者：Bo-Xiao Tang、Yue-Hua Zhang、Ren-Jie Song、Dong-Jun Tang、Guo-Bo Deng、Zhi-Qiang Wang、Ye-Xiang Xie、Yuan-Zhi Xia、Jin-Heng Li

  DOI：10.1021/jo300037n

  日期：2012.3.16

  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.
• ZnBr₂-Mediated oxidative spiro-bromocyclization of propiolamide for the synthesis of 3-bromo-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione
  作者：Yicheng He、Guanyinsheng Qiu

  DOI：10.1039/c7ob00293a

  日期：——

  ZnBr2-Mediated oxidative spiro-bromocyclization of N-arylpropiolamide has been described herein for the synthesis of 3-bromo-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione with high efficiency. One equivalent of water was introduced into the final product. The reaction efficiently proceeded at room temperature, and an excellent tolerance of functional groups was demonstrated. Under standard conditions

  本文已经描述了ZnBr 2介导的N-芳基丙酰胺酰胺的氧化螺-溴环化，用于高效合成3-溴-1-氮杂螺[4.5] deca-3,6,9-三烯-2,8-二酮。将一当量的水引入到最终产品中。该反应在室温下有效地进行，并且显示出优异的官能团耐受性。在标准条件下，3-溴-1-氧杂螺[4.5] deca-3,6,9-三烯-2,8-二酮和3-溴-1-氮杂螺[4.5] deca-3,6,9-trien-合成了8个。