N-benzoyl-4-(4-methoxyphenyl)-2,3-dihydro-1H-benzo[g]indole | 1428883-96-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-benzoyl-4-(4-methoxyphenyl)-2,3-dihydro-1H-benzo[g]indole
• 英文别名: [4-(4-Methoxyphenyl)-2,3-dihydrobenzo[g]indol-1-yl]-phenylmethanone；[4-(4-methoxyphenyl)-2,3-dihydrobenzo[g]indol-1-yl]-phenylmethanone
• CAS: 1428883-96-8
• 化学式: C₂₆H₂₁NO₂
• 分子量: 379.458
• InChiKey: JAQJNOJWYSIDSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-allyl-N-(1-(2-bromophenyl)-3-(4-methoxyphenyl)prop-2-yn-1-yl)benzamide 在 Grubbs catalyst first generation 、 乙烯 、 sodium acetate 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 14.0h， 生成 N-benzoyl-4-(4-methoxyphenyl)-2,3-dihydro-1H-benzo[g]indole
  参考文献：
  名称：

  Divergent Reaction Pathways of Homologous and Isosteric Propargyl Amides in Sequential Ru/Pd-Catalyzed Annulations for the Synthesis of Heterocycles

  摘要：

  Cu-catalyzed three-component coupling of imines with benzoyl chloride and terminal arylalkynes followed by enyne ring-closing metathesis (RCM) and Heck cyclization afforded medicinally relevant benzoindolines, cyclopropane-fused indenopyridines, pyrroloquinolines, or 1,7-tetrahydrophenanthrolines via divergent cyclization pathways. Unexpectedly, the Pd-catalyzed cyclization of heterocyclic dienes proceeded via regiodivergent 5-exo or 6-endo pathways depending on the ring size (n = 1, 2) or the presence of isosteric groups (CH vs N). A one pot protocol for the enyne-RCM/Heck annulation featuring a sequential addition of the Ru and Pd catalysts was developed maximizing the synthetic efficiency.

  DOI：

  10.1021/jo400246d

文献信息

• Divergent Reaction Pathways of Homologous and Isosteric Propargyl Amides in Sequential Ru/Pd-Catalyzed Annulations for the Synthesis of Heterocycles
  作者：Sandeep N. Raikar、Helena C. Malinakova

  DOI：10.1021/jo400246d

  日期：2013.4.19

  Cu-catalyzed three-component coupling of imines with benzoyl chloride and terminal arylalkynes followed by enyne ring-closing metathesis (RCM) and Heck cyclization afforded medicinally relevant benzoindolines, cyclopropane-fused indenopyridines, pyrroloquinolines, or 1,7-tetrahydrophenanthrolines via divergent cyclization pathways. Unexpectedly, the Pd-catalyzed cyclization of heterocyclic dienes proceeded via regiodivergent 5-exo or 6-endo pathways depending on the ring size (n = 1, 2) or the presence of isosteric groups (CH vs N). A one pot protocol for the enyne-RCM/Heck annulation featuring a sequential addition of the Ru and Pd catalysts was developed maximizing the synthetic efficiency.