(9-methylpyrido[2,1-a]isoindol-6-yl)(phenyl)methanone | 1111165-37-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (9-methylpyrido[2,1-a]isoindol-6-yl)(phenyl)methanone
• 英文别名: (9-Methylpyrido[1,2-b]isoindol-6-yl)-phenylmethanone；(9-methylpyrido[1,2-b]isoindol-6-yl)-phenylmethanone
• CAS: 1111165-37-7
• 化学式: C₂₀H₁₅NO
• 分子量: 285.345
• InChiKey: JJZMYSAAPKJEGS-UHFFFAOYSA-N

物化性质

• 熔点：
  145-148 °C
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  21.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(3-甲苯基)吡啶 、 苯乙炔 在 dirhodium tetraacetate 、 copper(l) iodide 、 copper diacetate 作用下， 以 N,N-二甲基乙酰胺 、 邻二甲苯 为溶剂， 以89%的产率得到(9-methylpyrido[2,1-a]isoindol-6-yl)(phenyl)methanone
  参考文献：
  名称：

  铑催化2-芳基吡啶与末端炔烃的直接氧化CH酰化反应：吡啶并[2,1- a ]异吲哚的合成

  摘要：

  AbstractA synthesis of pyrido[2,1‐a]isoindoles is reported by the rhodium‐catalyzed direct oxidative CH acylation of 2‐aryl pyridines with terminal alkynes. The desired products were obtained in moderate to excellent yields. This is an efficient and clean method to construct CC/CN bonds in one step. In addition, the effective rhodium(III) catalyst was isolated and characterized by X‐ray crystallography.magnified image

  DOI：

  10.1002/adsc.201400198

文献信息

• Facile Synthesis of Pyrido[2,1-a]isoindoles via Iron-Mediated 2-Arylpyridine C-H Bond Cleavage
  作者：Jiang Cheng、Shan Liu、Xingen Hu、Xinhua Li

  DOI：10.1055/s-0032-1318495

  日期：——

  An iron-catalyzed reaction of 2-arylpyridine C–H bond with 2-bromoacetophenone is achieved, providing pyrido[2,1-a]-isoindoles in moderate to good yields. The regioselectivity stems from the domination of hindrance on the regioselective ortho-functionalization of 2-arylpyridines C–H bond.

  实现了 2-芳基吡啶 C-H 键与 2-溴苯乙酮的铁催化反应，以中等至良好的产率提供吡啶并[2,1-a]-异吲哚。区域选择性源于对 2-芳基吡啶 C-H 键的区域选择性邻位官能化的阻碍。
• Multicomponent reactions of pyridines, α-bromo carbonyl compounds and silylaryl triflates as aryne precursors: a facile one-pot synthesis of pyrido[2,1-a]isoindoles
  作者：Xian Huang、Tiexin Zhang

  DOI：10.1016/j.tetlet.2008.10.118

  日期：2009.1

  Multicomponent reactions (MCRs) involving pyridines, α-bromo ketones, and silylaryl triflates as aryne precursors were investigated. The reactions could also be extended to isoquinoline or α-bromo ethyl acetate. Substituted pyrido[2,1-a]isoindoles or isoindolo[2,1-a]isoquinolines could be obtained from this routine, which may have potential applications in antitumor drugs and fluorescent material fields

  研究了涉及吡啶，α-溴代酮和甲硅烷基芳基三氟甲磺酸酯作为芳烃前体的多组分反应（MCR）。反应也可扩展至异喹啉或α-溴乙酸乙酯。取代的吡啶并[2,1-一个]异吲哚异吲哚或[2,1-一个]异喹啉类可以从该程序中，其可以具有在抗肿瘤药物和荧光材料领域的潜在应用而获得。
• Rhodium-Catalyzed Direct Oxidative CH Acylation of 2-Arylpyridines with Terminal Alkynes: A Synthesis of Pyrido[2,1-<i>a</i>]isoindoles
  作者：Binlin Zhao、Mengxuan Yu、Hui Liu、Yu Chen、Yu Yuan、Xuejian Xie

  DOI：10.1002/adsc.201400198

  日期：2014.11.3

  AbstractA synthesis of pyrido[2,1‐a]isoindoles is reported by the rhodium‐catalyzed direct oxidative CH acylation of 2‐aryl pyridines with terminal alkynes. The desired products were obtained in moderate to excellent yields. This is an efficient and clean method to construct CC/CN bonds in one step. In addition, the effective rhodium(III) catalyst was isolated and characterized by X‐ray crystallography.magnified image