6-methoxy-2-((4-methoxyphenyl)ethynyl)quinoline-3-carbaldehyde | 1430118-13-0

• 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: 6-methoxy-2-((4-methoxyphenyl)ethynyl)quinoline-3-carbaldehyde
• CAS: 1430118-13-0
• 化学式: C₂₀H₁₅NO₃
• 分子量: 317.344
• InChiKey: WNLMFHGFQYKKKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  48.42
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-methoxy-2-((4-methoxyphenyl)ethynyl)quinoline-3-carbaldehyde 在 potassium tert-butylate 、 双氧水 、 三氟甲磺酸钠 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以72%的产率得到7-methoxy-2-(4-methoxyphenyl)furo[3,2-b]quinoline
  参考文献：
  名称：

  通过异常 Dakin 型反应自由基促进合成呋喃喹啉

  摘要：

  通过微调从 2-炔基喹啉-3-甲醛中实现了选择性合成呋喃[3,2- b ]喹啉和亚苄基-1,3-二氢呋喃[3,4- b ]喹啉的自由基促进方法碱和氧化剂的高产率。在氧化剂的存在下，该反应通过Dakin 型反应通过脱羰分子内环化得到 5-endo-dig 环化呋喃喹啉；然而，在没有氧化剂的情况下，通过还原性分子内环化选择性地获得了 5-exo-dig 环化产物。X 射线晶体学研究进一步支持呋喃喹啉的形成。所提出的机制得到了控制实验的良好支持。

  DOI：

  10.1002/adsc.202100674
• 作为产物：
  描述：

  4-乙炔基苯甲醚 在 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 作用下， 以77%的产率得到6-methoxy-2-((4-methoxyphenyl)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

文献信息

• Chemoselective Azidation of <i>o</i>-Alkynylaldehydes over [3 + 2] Cycloaddition and Subsequent Staudinger Reaction: Access to Benzonaphthyridines/Naphthyridines
  作者：Pradeep Kumar、Trapti Aggarwal、Akhilesh K. Verma

  DOI：10.1021/acs.joc.7b01016

  日期：2017.6.16

  conditions is described. Mechanistic studies confirm the formation of azido-pyranoquinolines through nucleophilic attack of azide on pyrilium intermediate over [3 + 2] cycloaddition of the azide on the alkyne. The synthesized azido-pyranoquinolines were transformed into benzonaphthyridines via Staudinger reaction. The mechanistic pathway was supported by deuterium labeling experiment and X-ray crystallographic

  描述了一种在温和的反应条件下，在叠氮化钠存在下，通过邻炔基醛的亲电环化化学合成功能化的叠氮基-吡喃喹啉和叠氮基-碘吡喃并喹啉的有效串联方法。机理研究证实，叠氮化物在炔烃上的[3 + 2]环加成反应中，叠氮化物对pyr中间体的亲核攻击可形成叠氮基-吡喃喹啉。通过Staudinger反应将合成的叠氮基-吡喃喹啉转化为苯并萘啶。氘标记实验和X射线晶体学研究为该机理提供了支持。
• Harnessing the Reactivity of ortho-Alkynylaldehydes: Silver Triflate Catalyzed Regioselective Synthesis of Phosphonylated Fluorescent Molecules
  作者：Deepika Thakur、Shivam A. Meena、Akhilesh K. Verma、Sushmita Sushmita

  DOI：10.1055/a-2356-8347

  日期：2025.1

  An efficient approach for the facile synthesis of phosphonylated 1,3-dihydrofuro[3,4-b]quinolines and dihydrofuro[3,4-b]pyridines is developed. Reaction proceeds by the formation of new C–P and C–O bonds affording Z-selective phosphonylated products at room temperature. Diphenylphosphine oxides and dialkyl phosphites are explicitly incorporated into the carbonyl carbon of o-alkynylaldehydes in good

  开发了一种轻松合成膦酰化1,3-二氢呋喃并[3,4-b]喹啉和二氢呋喃并[3,4-b]吡啶的有效方法。反应通过形成新的 C-P 和 C-O 键进行，在室温下提供 Z-选择性膦酰化产物。二苯基氧化膦和亚磷酸二烷基酯以良好至优异的产率明确地结合到邻炔醛的羰基碳中。该反应条件温和，底物范围广泛，并在银催化剂存在下形成三个新键。机理研究表明，反应通过离子途径以 5-exo-dig 方式进行，产生 Z 选择性产物，并通过 X 射线晶体学研究得到验证。对所选化合物的光物理研究揭示了 455 nm 范围内的发射最大值。