(E)-tert-butyl 3-(2,7-Dioxo-5-phenyl-2,7,9,13b-tetrahydro-1H-pyrrolo[2,1-e] phenanthridin-6-yl) acrylate | 1364232-87-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (E)-tert-butyl 3-(2,7-Dioxo-5-phenyl-2,7,9,13b-tetrahydro-1H-pyrrolo[2,1-e] phenanthridin-6-yl) acrylate
• 英文别名: tert-butyl (E)-3-(2,7-dioxo-5-phenyl-9,13b-dihydro-1H-pyrrolo[2,1-e]phenanthridin-6-yl)prop-2-enoate
• CAS: 1364232-87-0
• 化学式: C₂₉H₂₇NO₄
• 分子量: 453.538
• InChiKey: XXERVTSHCPUQCX-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(2-iodobenzyl)-3-bromo-4-phenyl-1-azaspiro[4,5]deca-3,6,9-triene-2,8-dione 在 bis-triphenylphosphine-palladium(II) chloride 、 乙酰基乙酰对甲氧基苯胺 、 四丁基溴化铵 、 palladium diacetate 、 caesium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 120.0~130.0 ℃ 、101.33 kPa 条件下， 反应 17.0h， 生成 (E)-tert-butyl 3-(2,7-Dioxo-5-phenyl-2,7,9,13b-tetrahydro-1H-pyrrolo[2,1-e] phenanthridin-6-yl) acrylate
  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

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.