2-((4-(dimethylamino)phenyl)ethynyl)quinoline-3-carbaldehyde | 1430118-11-8

• 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: 2-((4-(dimethylamino)phenyl)ethynyl)quinoline-3-carbaldehyde
• CAS: 1430118-11-8
• 化学式: C₂₀H₁₆N₂O
• 分子量: 300.36
• InChiKey: ZQKKGUNTLDHDBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  33.2
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 2-((4-(dimethylamino)phenyl)ethynyl)quinoline-3-carbaldehyde 在 copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 反应 3.0h， 以89%的产率得到4-((1-methoxyfuro[3,4-b]quinolin-3(1H)-ylidene)methyl)-N,N-dimethylaniline
  参考文献：
  名称：

  Cu(I)-催化氧和氮亲核试剂触发呋喃/吡咯环环喹啉的区域选择性合成

  摘要：

  Cu(I) 催化的o -ethynylquinoline-3-carbaldehydes 的分子内环化导致通过 C-O 和 C-N 键的形成合成烷氧基/咪唑取代的 1,3-二氢呋喃[3,4- b ] 喹啉。该反应的范围进一步扩展到邻乙炔基喹啉-3-腈，用于使用醇作为亲核试剂合成烷氧基取代的 3 H-吡咯并[3,4- b ]喹啉。这些反应区域选择性地有利于所有环化过程中的 5 -exo-dig环化。

  DOI：

  10.1021/acs.joc.9b00662
• 作为产物：
  描述：

  4-二甲基氨基苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 作用下， 以75%的产率得到2-((4-(dimethylamino)phenyl)ethynyl)quinoline-3-carbaldehyde
  参考文献：
  名称：

  Silver-Catalyzed Tandem Synthesis of Naphthyridines and Thienopyridines via Three-Component Reaction

  摘要：

  An efficient approach for the silver-catalyzed regioselective tandem synthesis of highly functionalized 1,2-dihydorbenzo[1,6]naphthyridines 6a-z and 7a-e by the reaction of ortho-alkynylaldehydes 3a-n with amines 4a-d and ketones 5a-c/active methylene compounds 5d-g, under mild reaction conditions, is described. The scope of the developed chemistry was successfully extended for the direct synthesis of 1,2-dihydorbenzo[4,5]thieno[2,3-c]pyridines 8a-e, which is known as the sulfur analogue of beta-carbolines. Naphthyridines 6a-z and thienopyridines 8a-e were obtained via dual activation concept using L-proline as organocatalyst; however, naphthyridines 7a-e were synthesized without using organocatalyst. The reaction shows selective N-C bond formation on the more electrophilic alkynyl carbon, resulting in the regioselective 6-endo-digcyclized products. Reactivity behavior of electron-deficient and electron-rich ortho-alkynylaldehydes in the synthesis of naphthyridines and thienopyridine by three-component reaction is supported by the control experiment.

  DOI：

  10.1021/jo400400c