2-phenylethynyl-quinoline-3-carbaldehyde | 868765-12-2

• 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-phenylethynyl-quinoline-3-carbaldehyde
• 英文别名: 2-(Phenylethynyl)quinoline-3-carbaldehyde；2-(2-phenylethynyl)quinoline-3-carbaldehyde
• CAS: 868765-12-2
• 化学式: C₁₈H₁₁NO
• 分子量: 257.291
• InChiKey: RHZVKIRMWOGCHP-UHFFFAOYSA-N

物化性质

• 熔点：
  118 °C
• 沸点：
  474.8±30.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenylethynyl-quinoline-3-carbaldehyde 在 potassium phosphate 、 silver trifluoromethanesulfonate 作用下， 以 乙醇 为溶剂， 反应 0.17h， 生成 2-methyl-5-phenylbenzo[b]pyrazolo[5,1-f][1,6]naphthyridine
  参考文献：
  名称：

  Convenient synthesis of benzo[b]pyrazolo[5,1-f][1,6]naphthyridines by silver triflate catalyzed three-component reaction of 2-alkynyl-3-formylquinolines, tosylhydrazine and carbonyl compounds

  摘要：

  Benzo[b]pyrazolo[5,1-f][1,6]naphthyridines were prepared by silver triflate catalyzed one-pot cyclization of tosylhydrazine, carbonyl compounds and 2-alkynyl-3-formylquinolines, which are available by Sonogashira reaction of 2-chloro-3-formylquinoline. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.060
• 作为产物：
  描述：

  苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 作用下， 生成 2-phenylethynyl-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

• Novel Synthetic Method of 2-(2-Oxoethyl)-1H-indole-3-carbaldehydes
  作者：Inga Cikotiene、Rita Buksnaitiene

  DOI：10.1055/s-0030-1260317

  日期：2011.10

  The smooth and regioselective synthesis of 2-(2-oxo­ethyl)-1H-indole-3-carbaldehydes via silver-catalyzed 6-endo-dig acetalization-cyclization reaction followed by immediate hydrolysis of the unstable 1-alkoxypyrano[4,3-b]indole intermediates is described.

  本文报道了通过银催化的6-endo-dig缩酮化-环化反应，合成2-(2-氧代乙基)-1H-吲哚-3-甲醛，随后立即水解不稳定的1-烷氧基吡喃并[4,3-b]吲哚中间体的过程。
• Formation of Condensed 1<i>H</i>-Pyrrol-2-ylphosphonates and 1,2-Dihydropyridin-2-ylphosphonates via Kabachnik–Fields Reaction of Acetylenic Aldehydes and Subsequent 5-<i>exo</i>-<i>dig</i> or 6-<i>endo</i>-<i>dig</i> Cyclizations
  作者：Rita Bukšnaitienė、Aurelija Urbanaitė、Inga Čikotienė

  DOI：10.1021/jo501011u

  日期：2014.7.18

  Kabachnik–Fields reactions of various carbocyclic or heterocyclic acetylenic aldehydes together with subsequent Lewis acid catalyzed cyclizations have been studied. It was found that 5-exo-dig versus 6-endo-dig cyclization mode strongly depends on the structure of starting materials. Thus, nonaromatic acetylenic α-anilinomethylphosphonates underwent gold(III)-catalyzed or iodine-mediated 5-exo-dig

  研究了各种碳环或杂环炔醛的Kabachnik-Fields反应以及随后的路易斯酸催化的环化反应。发现5- exo - dig与6- endo - dig环化模式在很大程度上取决于起始材料的结构。因此，非芳族炔属α-苯胺基甲基膦酸酯经历了金（III）催化或碘介导的5- exo - dig环化成1 H-吡咯-2-基膦酸酯。与此相反，吸电子的杂芳族的基体构成通过专用6-含材料-1,2-二氢吡啶-2- ylphosphonate环内-挖闭环过程。仅对于含有苯环的α-氨基（2-炔基苯基）甲基膦酸酯，双环化是可能的。
• Catalytic formal [4 + 1] isocyanide-based cycloaddition: an efficient strategy for the synthesis of 1<i>H</i>-cyclopenta[<i>b</i>]quinolin-1-one derivatives
  作者：Milad Motaghi、Hormoz Khosravi、Saeed Balalaie、Frank Rominger

  DOI：10.1039/c8ob02857e

  日期：——

  unprecedented catalytic isocyanide-based cycloaddition of alkyl and aryl isocyanides with (Z)-2-(2-hydroxy-2-alkylvinyl)quinoline-3-carbaldehydes was developed for the direct and efficient synthesis of 1H-cyclopenta[b]quinolin-1-one derivatives. On the basis of DFT calculations, a mechanism is proposed involving formal [4 + 1] cycloaddition of isocyanides, followed by imine–enamine tautomerization and air

  开发了一种空前的基于异氰酸酯催化的烷基和芳基异氰酸酯与（Z）-2-（2-羟基-2-烷基乙烯基）喹啉-3-甲醛的环加成反应，以直接有效地合成1 H-环戊基[ b ]喹啉。 -1-一阶导数。在DFT计算的基础上，提出了一种机制，其中涉及异氰酸酯的正式[4 +1]环加成，然后进行亚胺-烯胺互变异构化和空气氧化。
• Site-Selective Electrophilic Cyclization and Subsequent Ring-Opening: A Synthetic Route to Pyrrolo[1,2-<i>a</i>]quinolines and Indolizines
  作者：Trapti Aggarwal、Sonu Kumar、Devendra K. Dhaked、Rakesh K. Tiwari、Prasad V. Bharatam、Akhilesh K. Verma

  DOI：10.1021/jo3015374

  日期：2012.10.5

  An efficient strategy for the synthesis of pyrrolo[1,2-a]quinolines and indolizines from pyranoquinolines via site-selective electrophilic cyclization and subsequent opening of pyran ring using silver/iodine under mild reaction conditions is described. This approach involves the preferential attack of the pyridyl nitrogen over aryl ring and leads to the formation of 5-endo-dig cyclized products. Quantum

  描述了一种通过位点选择性亲电环化从吡喃并喹啉合成吡咯并[1,2- a ]喹啉和吲哚嗪的有效策略，随后在温和的反应条件下使用银/碘打开吡喃环。这种方法涉及的吡啶基的氮的优先攻击过的芳环，并导致5-地层内切-挖环化产物。C–N（ΔE a = 9.01 kcal / mol）和C–C（ΔE a为了使观察到的位点选择性合理化，进行＝ 31.31kcal / mol）的键形成。通过X射线晶体学研究证实了产物的结构。通过Pd催化的交叉偶联反应，通过亲电碘化反应生成的碘取代的化合物进一步多样化。
• Silver-Catalyzed Domino Hydroarylation/Cycloisomerization Reactions of 2-Alkynylquinoline-3-carbaldehydes: Access to (Hetero)arylpyranoquinolines
  作者：Véronique Michelet、Philippe Belmont、Alexis Bontemps、Gaëlle Mariaule、Stéphanie Desbène-Finck、Philippe Helissey、Sylviane Giorgi-Renault

  DOI：10.1055/s-0035-1562234

  日期：——

  trifluoromethanesulfonate catalyzed efficient access to the indolylpyranoquinoline scaffold is reported. Starting from 2-alkynylquinoline-3-carbaldehyde units with various substitution patterns on the quinoline and alkynyl parts, the use of silver trifluoromethanesulfonate (10 mol%) in 1,2-dichloroethane allowed a domino hydroarylation/cycloisomerization reaction, generating (hetero)aryl-functionalized pyranoquinolines

  摘要 据报道，三氟甲磺酸银催化有效地获得了吲哚基吡喃喹啉骨架。从在喹啉和炔基部分上具有各种取代模式的2-炔基喹啉-3-甲醛单元开始，在1,2-二氯乙烷中使用三氟甲磺酸银（10 mol％）可以进行多米诺加氢芳基化/环异构化反应，生成（杂）芳基-官能化的吡喃喹啉。所使用的杂芳烃为N-甲基吲哚（18种化合物，占67-100％），吲哚和2-甲基吲哚（4种化合物，占36-89％），并且该反应与芳烃（例如吡咯）的相容性较小（5种化合物，占43-90％），1,3,5-三甲氧基苯和3-甲基苯并呋喃。 据报道，三氟甲磺酸银催化有效地获得了吲哚基吡喃喹啉骨架。从在喹啉和炔基部分上具有各种取代模式的2-炔基喹啉-3-甲醛单元开始，在1,2-二氯乙烷中使用三氟甲磺酸银（10 mol％）可以进行多米诺加氢芳基化/环异构化反应，生成（杂）芳基-官能化的吡喃喹啉。所使用的杂芳烃为N-甲基吲哚（18种化合物，占67-10

表征谱图