2-(pyridin-2-yl)ethynyl-quinoline-2-carbaldehyde | 852435-17-7

• 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-(pyridin-2-yl)ethynyl-quinoline-2-carbaldehyde
• 英文别名: 2-(2-Pyridin-2-ylethynyl)quinoline-3-carbaldehyde；2-(2-pyridin-2-ylethynyl)quinoline-3-carbaldehyde
• CAS: 852435-17-7
• 化学式: C₁₇H₁₀N₂O
• 分子量: 258.279
• InChiKey: HIDGLUOQSMREEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(pyridin-2-yl)ethynyl-quinoline-2-carbaldehyde 在 aluminum oxide 、 4 A molecular sieve 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.25h， 生成
  参考文献：
  名称：

  An Efficient and Simple Aminobenzannulation Reaction:  Pyrrolidine as a Trigger for the Synthesis of 1-Amino-acridines

  摘要：

  A new aminobenzannulation methodology has been developed and applied successfully to the synthesis of 1-amino-acridines. The key and last step goes through an enamine intermediate that was detected in some cases. When pyrrolidine and powdered 4 angstrom molecular sieves were used, the enamine synthesis and the aminobenzannulation step took place subsequently, whereas for other secondary amines, neutral Al2O3 or PtCl2 catalysis was necessary.

  DOI：

  10.1021/ol050380z
• 作为产物：
  描述：

  2-乙炔基吡啶 、 2-氯-3-喹啉甲醛 生成 2-(pyridin-2-yl)ethynyl-quinoline-2-carbaldehyde
  参考文献：
  名称：

  碱性介质中乙炔醛与亚磷酸二甲酯的反应研究：膦酸酯-磷酸盐重排与5 - exo- dig环化反应

  摘要：

  在碱性介质中研究了各种炔醛与亚磷酸二甲酯的串联反应。已经表明，在起始材料的未活化的三键的情况下，发生了众所周知的Pudovik反应，随后发生了膦酸酯-磷酸盐的重排。另一方面，当起始材料的三键被吸电子杂环激活时，顺畅且区域选择性的串联5-外切-环化反应成为可能。

  DOI：

  10.1002/adsc.201200276

文献信息

• Synthesis of cyclopentaquinolinone and cyclopentapyridinone from <i>ortho</i>-alkynyl-<i>N</i>-arylaldehyde <i>via</i> superbase-promoted C–N, C–O and C–C bond formation
  作者：Kapil Mohan Saini、Rakesh K. Saunthwal、Sushmita、Akhilesh K. Verma

  DOI：10.1039/d0ob01281e

  日期：——

  and cyclopentapyridinones via C–N, C–C, and CO bond formation. Contrary to the traditional approaches of ring closures, a different mode of annulation is disclosed. The protocol involves the in situ generations of imine intermediate followed by potassium hydroxide-promoted intramolecular cyclization and subsequent dimethyl sulfoxide induced dehydrogenation leads to the formation of N-heterocycles. X-ray

  邻炔基醛与伯胺的无环环境友好，无过渡金属，超碱介导的分子内环化反应会通过C–N，C–C和C O键的形成形成高度官能化的氨基取代的环戊喹啉酮和环戊二吡啶酮。与传统的环闭合方法相反，公开了一种不同的环行方式。该方案涉及原位生成亚胺中间体，然后进行氢氧化钾促进的分子内环化反应，随后由二甲基亚砜诱导的脱氢作用导致N杂环的形成。X射线晶体学研究支持氨基稠合的N-杂环的指定结构。
• Dual function of carbon tetrachloride: synthesis of chlorinated heterocycles
  作者：Shiv Kumar、Rakesh K. Saunthwal、Kapil M. Saini、Akhilesh K. Verma

  DOI：10.1039/c9cc04746h

  日期：——

  An efficient tandem approach to invent highly chlorinated and structurally diversified dihydropyridine fused heterocycles from easily accessible ortho-alkynylaldehydes and primary amines under metal-free conditions via four sequential bond formations is described. The proposed tandem route proceeds via a carbon tetrachloride-mediated 6-endo-dig ring closure followed by nucleophilic attack of the trichloromethyl

  描述了一种有效的串联方法，该方法可在无金属条件下通过四个连续的键形成方法，从容易获得的邻炔基乙醛和伯胺中发明高度氯化且结构多样的二氢吡啶稠合杂环。所提出的串联途径是通过四氯化碳介导的6-内切开环闭合，随后是对三氯甲基阴离子的亲核攻击。
• A novel and simple benzannulation reaction using the potassium salt of methyl mercaptoacetate for the synthesis of 3-aryl-2-methoxycarbonylacridines
  作者：Inga Cikotiene

  DOI：10.1016/j.tetlet.2009.03.072

  日期：2009.5

  A new benzannulation methodology has been developed and applied to the synthesis of 3-aryl-2-methoxycarbonylacridines.

  已经开发出一种新的苯并环方法，并将其应用于3-芳基-2-甲氧基羰基ac啶的合成。
• Silver-catalyzed furoquinolines synthesis: from nitrogen effects to the use of silver imidazolatepolymer as a new and robust silver catalyst
  作者：Evelyne Parker、Nicolas Leconte、Thomas Godet、Philippe Belmont

  DOI：10.1039/c0cc02623a

  日期：——

  Silver-catalyzed tandem acetalization and cycloisomerization reactions were found to lead to various furoquinolines, and a nitrogen effect was noticed for AgOTf reactivity, since the cyclization mode switched from 6-endo-dig to 5-exo-dig; from these observations silver imidazolate polymer is proposed as a stable silver catalyst.

  研究发现，银催化的串联缩醛化和环异构化反应可生成各种呋喃喹啉类化合物，而且由于环化模式从 6-endo-dig 转变为 5-exo-dig，AgOTf 的反应活性还受到氮效应的影响。
• An Efficient and Simple Aminobenzannulation Reaction:  Pyrrolidine as a Trigger for the Synthesis of 1-Amino-acridines
  作者：Philippe Belmont、Tahar Belhadj

  DOI：10.1021/ol050380z

  日期：2005.4.1

  A new aminobenzannulation methodology has been developed and applied successfully to the synthesis of 1-amino-acridines. The key and last step goes through an enamine intermediate that was detected in some cases. When pyrrolidine and powdered 4 angstrom molecular sieves were used, the enamine synthesis and the aminobenzannulation step took place subsequently, whereas for other secondary amines, neutral Al2O3 or PtCl2 catalysis was necessary.