3-iodo-2-methyl-4-quinolinylamine | 543740-73-4

• 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: 3-iodo-2-methyl-4-quinolinylamine
• 英文别名: 4-Amino-3-iodo-2-methylquinoline；3-iodo-2-methylquinolin-4-amine
• CAS: 543740-73-4
• 化学式: C₁₀H₉IN₂
• 分子量: 284.099
• InChiKey: GXKCJUGMQQSGBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-iodo-2-methyl-4-quinolinylamine 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 反应 20.0h， 生成 2-butyl-4-methyl-1H-pyrrolo[3,2-c]quinoline
  参考文献：
  名称：

  Synthesis of polyfunctional indoles and related heterocycles mediated by cesium and potassium bases

  摘要：

  A general preparation of 2-substituted indoles starting from functionalized 2-alkynylanilines has been developed. This base mediated reaction has also been used to synthesize the heterocyclic core of the marine alkaloid hinckdentine A. Furthermore the reaction was successfully adapted to the solid phase. Benzofurans and isoindolones could also be prepared with this method. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00073-5
• 作为产物：
  描述：

  4-氨基喹哪啶 在 N-碘代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以39%的产率得到3-iodo-2-methyl-4-quinolinylamine
  参考文献：
  名称：

  Synthesis of polyfunctional indoles and related heterocycles mediated by cesium and potassium bases

  摘要：

  A general preparation of 2-substituted indoles starting from functionalized 2-alkynylanilines has been developed. This base mediated reaction has also been used to synthesize the heterocyclic core of the marine alkaloid hinckdentine A. Furthermore the reaction was successfully adapted to the solid phase. Benzofurans and isoindolones could also be prepared with this method. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00073-5

文献信息

• Catalytic Activation of Trimethylsilylacetylenes: A One-Pot Route to Unsymmetrical Acetylenes and Heterocycles
  作者：Dániel Lasányi、Ádám Mészáros、Zoltán Novák、Gergely L. Tolnai

  DOI：10.1021/acs.joc.8b00998

  日期：2018.8.3

  the synthesis of unsymmetrical acetylenes, a Sonogashira coupling–deprotection–Sonogashira coupling reaction sequence is often used. Removal of protecting groups requires harsh conditions or an excess of difficult to handle and expensive reagents. Herein, we disclose a novel catalytic method for the selective deprotection of trimethylsilylacetylenes in Sonogashira reaction. The reagent hexafluorosilicic

  对于不对称乙炔的合成，通常使用Sonogashira偶联-去保护-Sonogashira偶联反应顺序。除去保护基需要苛刻的条件或过多的难以处理和昂贵的试剂。在这里，我们公开了一种新颖的催化方法，用于在Sonogashira反应中选择性脱保护三甲基甲硅烷基乙炔。六氟硅酸试剂是一种廉价的无毒化合物，用于促进选择性去甲硅烷基化。该方法能够有效地合成存在其他甲硅烷基化官能团的不对称乙炔。通过杂环的合成探索了该方法的其他可能性。
• Synthesis of polyfunctional indoles and related heterocycles mediated by cesium and potassium bases
  作者：Christopher Koradin、Wolfgang Dohle、Alain L Rodriguez、Bertram Schmid、Paul Knochel

  DOI：10.1016/s0040-4020(03)00073-5

  日期：2003.2

  A general preparation of 2-substituted indoles starting from functionalized 2-alkynylanilines has been developed. This base mediated reaction has also been used to synthesize the heterocyclic core of the marine alkaloid hinckdentine A. Furthermore the reaction was successfully adapted to the solid phase. Benzofurans and isoindolones could also be prepared with this method. (C) 2003 Elsevier Science Ltd. All rights reserved.