2-((4-nitrophenyl)ethynyl)quinoline-3-carbaldehyde | 1430118-15-2

• 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-((4-nitrophenyl)ethynyl)quinoline-3-carbaldehyde
• CAS: 1430118-15-2
• 化学式: C₁₈H₁₀N₂O₃
• 分子量: 302.289
• InChiKey: SAMHPYWYHFPAIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 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：
  0.0
• 拓扑面积：
  73.1
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-((4-nitrophenyl)ethynyl)quinoline-3-carbaldehyde 在 水 、 silver nitrate 、 zinc(II) iodide 作用下， 以 1,4-二氧六环 、 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 (3,4-diphenyl-5H-azepino[4,3-b]quinolin-5-yl)(4-nitrophenyl)methanone
  参考文献：
  名称：

  通过 2H-Azirines 的级联开环/环化反应通过正式 [4+3] 和 [4+2] 环化合成萘啶和氮杂庚烷主链

  摘要：

  在这项工作中，报道了 2 H-氮杂环丙烷和烯醇化-o-炔基喹啉甲醛的级联开环环化作为在锌催化剂存在下合成萘啶和吖庚因骨架的双功能前体。该方法通过正式 [4+3] 和 [4+2] 环化形成两个新键（C=N 和 C=C 键）和裂解，为构建新型稠合杂环提供了一种实用且直接的方法2 H -azirine C−C 键在一个步骤中。

  DOI：

  10.1002/ejoc.202201109
• 作为产物：
  描述：

  N-乙酰苯胺 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.58h， 生成 2-((4-nitrophenyl)ethynyl)quinoline-3-carbaldehyde
  参考文献：
  名称：

  顺序碱基促进的形式 [4+2] 烯丙酸酯基环加成：功能化吖啶的合成

  摘要：

  ( Z )-2-(2-羟基-2-烷基乙烯基)quinoline-3-carbaldehydes 和 allenoates在碱促进的形式 [4+2] 环加成反应中的顺序迈克尔加成、醛醇缩合和异构化过程提供了一种有效的在温和条件下产生官能化吖啶的方法。

  DOI：

  10.1002/ejoc.202200830

文献信息

• Stereoselective tandem synthesis of thiazolo fused naphthyridines and thienopyridines from o-alkynylaldehydes via Au(<scp>iii</scp>)-catalyzed regioselective 6-endo-dig ring closure
  作者：Rajeev R. Jha、Rakesh K. Saunthwal、Akhilesh K. Verma

  DOI：10.1039/c3ob42035c

  日期：——

  An operationally simple approach for the stereoselective tandem synthesis of novel thiazolo fused naphthyridines 5a–o and thienopyridines 8a–e by the reaction of o-alkynylaldehydes with L-cystine methyl ester hydrochloride via Au(III)-catalyzed regioselective 6-endo-dig ring closure under mild reaction conditions is described. It is noteworthy that alkynes bearing an alkyl and a strong electron-withdrawing nitro group successfully afforded the desired products in good yields.

  本研究介绍了一种操作简单的方法，即在温和的反应条件下，通过 Au(III) 催化的区域选择性 6-endo-dig 封环反应，使邻炔醛与 L-胱氨酸甲酯盐酸盐发生反应，从而立体选择性地串联合成新型噻唑并萘啶 5a-o 和噻吩并吡啶 8a-e。值得注意的是，带有一个烷基和一个强夺电子硝基的炔烃成功地以良好的收率得到了所需的产物。
• Transition-metal-free approaches to 2,3-diarylated indenones from 2-alkynylbenzaldehydes and phenols with tunable selectivity
  作者：Tuanli Yao、Shuaijing Zhao、Tao Liu、Yuting Wu、Yanhui Ma、Tao Li、Xiangyang Qin

  DOI：10.1039/d2cc01324j

  日期：——

  The first transition-metal-free synthesis of 2,3-diarylindenones with tunable selectivity via tandem annulation of 2-alkynylbenzaldehydes with phenols has been developed.

  通过2-炔基苯甲醛与酚的串联环化反应，开发出了第一个无过渡金属合成2,3-二芳基茚酮的方法，其选择性可调。
• Silver-Catalyzed Tandem Synthesis of Naphthyridines and Thienopyridines via Three-Component Reaction
  作者：Akhilesh K. Verma、Siva K. Reddy Kotla、Deepak Choudhary、Monika Patel、Rakesh K. Tiwari

  DOI：10.1021/jo400400c

  日期：2013.5.3

  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.
• Au(III)-catalyzed regio- and stereoselective tandem synthesis of oxazolo fused naphthyridines and isoquinolines from o-alkynylaldehydes
  作者：Rajeev Ranjan Jha、Abhinandan Kumar Danodia、Sushil Kumar、Akhilesh Kumar Verma

  DOI：10.1016/j.tetlet.2013.11.072

  日期：2014.1

  An efficient tandem approach for the regio- and stereoselective synthesis of oxazolo-fused naphthyridines 3a-g, 3i-l and isoquinolines 3h, 3m via the reaction of o-alkynylaldehydes 1a-i with chiral amino alcohols 2a-c under mild reaction conditions is described. The stereochemistry and structures of the products were assigned via NOESY and X-ray crystallographic studies. (C) 2013 Elsevier Ltd. All rights reserved.