7-methoxy-9-phenylfuro[3,4-b]quinolin-3(1H)-one | 1184181-81-4

• 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: 7-methoxy-9-phenylfuro[3,4-b]quinolin-3(1H)-one
• 英文别名: 7-methoxy-9-phenyl-1H-furo[3,4-b]quinolin-3-one
• CAS: 1184181-81-4
• 化学式: C₁₈H₁₃NO₃
• 分子量: 291.306
• InChiKey: KHDWWZRVFAITIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-phenylprop-2-yn-1-yl (4-methoxyphenyl)glycinate 在 oxone||potassium monopersulfate triple salt 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以61%的产率得到7-methoxy-9-phenylfuro[3,4-b]quinolin-3(1H)-one
  参考文献：
  名称：

  Oxone 促进 N-芳基甘氨酸衍生物的脱氢波瓦罗夫环化：一种处理喹啉稠合内酯和内酰胺的方法†

  摘要：

  已经探索了Oxone 促进了炔烃连接的N-芳基甘氨酸酯和酰胺的分子内脱氢亚氨基 Diels-Alder 反应（Povarov 环化），从而提供了具有生物学意义的喹啉稠合内酯和内酰胺。该反应简单、可扩展且产率高（高达 88%）。该方法进一步扩展到制备具有生物学重要意义的luotonin-A类似物和环沙霉素的喹啉核心。

  DOI：

  10.1039/c9ra06212b

文献信息

• Intramolecular Imino Diels−Alder Reaction: Progress toward the Synthesis of Uncialamycin
  作者：Sandy Desrat、Pierre van de Weghe

  DOI：10.1021/jo901291t

  日期：2009.9.4

  We herein described an intramolecular imino Diels−Alder reaction promoted with BF3·OEt2/DDQ affording substituted quinolines. Using this procedure, we prepared the chiral quinoline moiety of the uncialamycin, a new enediyne natural product.

  我们在本文中描述了用BF 3 ·OEt 2 / DDQ促进的分子内亚氨基Diels-Alder反应，提供了取代的喹啉。使用该程序，我们制备了一种新烯二炔天然产物非那霉素的手性喹啉部分。
• One‐Pot Synthesis of Highly Substituted Quinolines in Aqueous Medium and Its Application for the Synthesis of Azalignans
  作者：Amrendra Kumar、Ramanand Prajapati、Ruchir Kant、Tadigoppula Narender

  DOI：10.1002/ejoc.202000906

  日期：2020.9.14

  A one‐pot synthesis of highly substituted quinolines is reported. The sequence starts with the C(sp3)‐H functionalization of α‐amino ketone derivatives, glycine esters, or glycine amide in the presence of iodine. Subsequently, a nucleophilic substitution with alkynes or alkynyl esters takes place. An aerobic oxidative aromatization in water with sodium dodecyl sulfate (SDS) as surfactant gives the

  据报道一锅法合成高度取代的喹啉。该序列始于在碘存在下α-氨基酮衍生物，甘氨酸酯或甘氨酸酰胺的C（sp 3）-H官能化。随后，用炔烃或炔基酯进行亲核取代。以十二烷基硫酸钠（SDS）为表面活性剂在水中进行好氧氧化芳构化，喹啉的收率中等至良好。
• Oxidative Tandem Cyclization of Glycine Esters with Propargyl Alcohols
  作者：Tongzhi Sang、Jia Liang、Songhai Huang、Guozhe Guo、Jie Yang、Xiazhen Bao、Congde Huo

  DOI：10.1021/acs.joc.3c00627

  日期：2023.7.21

  A facile and efficient aerobic oxidative (4 + 2)-cyclization/aromatization/lactonization tandem reaction of N-aryl glycine esters with propargyl alcohols to access quinoline-fused lactones is reported. The reaction can be extended to homopropargylic alcohols too. The transformation is straightforward to perform under mild conditions and scalable, and both reaction components are readily available.

  据报道， N-芳基甘氨酸酯与炔丙醇进行简单有效的有氧氧化（4+2）环化/芳构化/内酯化串联反应，得到喹啉稠合内酯。该反应也可以扩展到均炔醇。该转化在温和条件下进行很简单并且可扩展，并且两种反应组分都很容易获得。
• Catalytic Radical Cation Salt Induced C_sp³–H Functionalization of Glycine Derivatives: Synthesis of Substituted Quinolines
  作者：Xiaodong Jia、Fangfang Peng、Chang Qing、Congde Huo、Xicun Wang

  DOI：10.1021/ol301909g

  日期：2012.8.3

  A domino C-sp3-H functionalization of glycine derivatives was achieved under catalytic radical cation salt induced conditions, producing a series of quinolines. The proposed mechanism shows that a peroxyl radical cation, which is generated by the coupling between O-2 and TBPA(+center dot), might be involved to initiate the catalytic oxidation.
• Radical Cation Salt-Promoted Catalytic Aerobic sp³ C–H Oxidation: Construction of Quinoline-Fused Lactones and Lactams
  作者：Yaxin Wang、Fangfang Peng、Jing Liu、Congde Huo、Xicun Wang、Xiaodong Jia

  DOI：10.1021/jo502184k

  日期：2015.1.2

  A direct construction of quinoline-fused lactones and lactams was achieved by sp(3) C-H bond oxidation of N-aryl glycine esters and amides under catalytic radical cation salt-induced conditions. These polycyclic products are formed in a single step from readily accessible starting materials, and this method provides a new synthetic approach to this class of heterocycles.