4-phenyl-3-(2-phenylethynyl)isoquinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-phenyl-3-(2-phenylethynyl)isoquinoline
• 化学式: C₂₃H₁₅N
• 分子量: 305.379
• InChiKey: GFOITRGEBMQBCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-phenyl-3-(2-phenylethynyl)isoquinoline 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium acetate 、 一氯化碘 、 sodium chloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 42.33h， 生成 7,8-diphenylbenzo[a]naphtho[1,2-c]phenanthridine
  参考文献：
  名称：

  连续三组分串联反应和6-内碳环化反应合成8-芳基取代的苯并[ a ]菲啶衍生物

  摘要：

  描述了一种简明的苯并[ a ]菲啶结构，涉及顺序形式的多组分串联反应/碳环化。该反应首先通过以三组分形式由2-溴苯甲醛/叔丁胺/ 1,3-二炔形成4-芳基-3-芳基乙炔基-异喹啉，然后通过金/银催化的分子内加氢芳基化进行第二次闭环或通过碘催化的区域选择性6-内切-亲电环化。该策略的显着特征涉及三组分反应，然后分两步将所得产物转化为结构复杂度增加的多杂环化合物。

  DOI：

  10.1016/j.tet.2012.07.067
• 作为产物：
  描述：

  2-碘苯甲醛 在 palladium diacetate 、 水 、 sodium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 4-phenyl-3-(2-phenylethynyl)isoquinoline
  参考文献：
  名称：

  Synthesis of Isoquinolines and Pyridines by the Palladium-Catalyzed Iminoannulation of Internal Alkynes

  摘要：

  A wide variety of substituted isoquinoline, tetrahydroisoquinoline, 5,6-dihydrobenz[f]isoquinoline, pyrindine, and pyridine heterocycles have been prepared in good to excellent yields via annulation of internal acetylenes with the tert-butylimines of o-iodobenzaldehydes and 3-halo-2-alkenals in the presence of a palladium catalyst. The best results are obtained by employing 5 mol % of Pd(OAc)(2), an excess of the alkyne, 1 equiv of Na2CO3 as a base, and 10 mol % of PPh3 in DMF as the solvent. This annulation methodology is particularly effective for aryl- or alkenyl-substituted alkynes. When electron-rich imines are employed, this chemistry can be extended to alkyl-substituted alkynes. Trimethylsilyl-substituted alkynes also undergo this annulation process to afford monosubstituted heterocyclic products absent the silyl group.

  DOI：

  10.1021/jo0105540

文献信息

• Synthesis of Isoquinolines and Pyridines via Palladium-Catalyzed Iminoannulation of Internal Acetylenes
  作者：Kevin R. Roesch、Richard C. Larock

  DOI：10.1021/jo980871f

  日期：1998.8.1
• Synthesis of Isoquinolines and Pyridines by the Palladium-Catalyzed Iminoannulation of Internal Alkynes
  作者：Kevin R. Roesch、Haiming Zhang、Richard C. Larock

  DOI：10.1021/jo0105540

  日期：2001.11.1

  A wide variety of substituted isoquinoline, tetrahydroisoquinoline, 5,6-dihydrobenz[f]isoquinoline, pyrindine, and pyridine heterocycles have been prepared in good to excellent yields via annulation of internal acetylenes with the tert-butylimines of o-iodobenzaldehydes and 3-halo-2-alkenals in the presence of a palladium catalyst. The best results are obtained by employing 5 mol % of Pd(OAc)(2), an excess of the alkyne, 1 equiv of Na2CO3 as a base, and 10 mol % of PPh3 in DMF as the solvent. This annulation methodology is particularly effective for aryl- or alkenyl-substituted alkynes. When electron-rich imines are employed, this chemistry can be extended to alkyl-substituted alkynes. Trimethylsilyl-substituted alkynes also undergo this annulation process to afford monosubstituted heterocyclic products absent the silyl group.
• Synthesis of 8-aryl substituted benzo[a]phenanthridine derivatives by consecutive three component tandem reaction and 6-endo carbocyclization
  作者：Anil K. Mandadapu、Meena D. Dathi、Rajesh K. Arigela、Bijoy Kundu

  DOI：10.1016/j.tet.2012.07.067

  日期：2012.9

  of benzo[a]phenanthridines involving multicomponent tandem reaction/carbocyclization in a sequential format is described. The reaction proceeds initially via formation of a 4-aryl-3-arylethynyl-isoquinoline from 2-bromobenzaldehyde/tert-butylamine/1,3-diyne in a three component format followed by a second ring closure either via gold/silver catalyzed intramolecular hydroarylation or via iodo-catalyzed

  描述了一种简明的苯并[ a ]菲啶结构，涉及顺序形式的多组分串联反应/碳环化。该反应首先通过以三组分形式由2-溴苯甲醛/叔丁胺/ 1,3-二炔形成4-芳基-3-芳基乙炔基-异喹啉，然后通过金/银催化的分子内加氢芳基化进行第二次闭环或通过碘催化的区域选择性6-内切-亲电环化。该策略的显着特征涉及三组分反应，然后分两步将所得产物转化为结构复杂度增加的多杂环化合物。