3-phenyl-1H-pyrano[4,3-b]quinolin-1-one | 1353646-04-4

• 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: 3-phenyl-1H-pyrano[4,3-b]quinolin-1-one
• 英文别名: 3-phenylpyrano[4,3-b]quinolin-1-one
• CAS: 1353646-04-4
• 化学式: C₁₈H₁₁NO₂
• 分子量: 273.291
• InChiKey: PKZKBXXJWDTXHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-phenylethynylquinoline-3-carboxylic acid methyl ester 在 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以92%的产率得到3-phenyl-1H-pyrano[4,3-b]quinolin-1-one
  参考文献：
  名称：

  An economical nucleophilic route toward facile synthesis of pyrano[4,3-b]quinolin-1-ones via 6-endo-dig cyclization of o-alkynylquinoline esters

  摘要：

  Metal-free facile synthesis of pyrano[4,3-b]quinoline-1-ones is described from methyl 2-arylethynyl-quinoline-3-carboxylates via intramolecular cyclization in excellent yields. The cyclization reactions are facilitated using cheap and easily available KOH base in MeOH. The reaction conditions did not require dry solvent, inert atmosphere, and avoid further column chromatography purification of the products. These compounds could be further used as building blocks for the synthesis of 2H-benzo[b][1,6]naphthyridin-1-one and 1-chloro-benzo[b][1,6]naphthyridines. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.068

文献信息

• Modular synthesis of 3-substituted isocoumarins <i>via</i> silver-catalyzed aerobic oxidation/<i>6-endo</i> heterocyclization of <i>ortho</i>-alkynylbenzaldehydes
  作者：Hao Wu、Yi-Chun Wang、Andrey Shatskiy、Qiu-Yan Li、Jian-Quan Liu、Markus D. Kärkäs、Xiang-Shan Wang

  DOI：10.1039/d1ob01065d

  日期：——

  A method involving silver-catalyzed aerobic oxidation/6-endo heterocyclization of ortho-alkynylbenzaldehydes to yield 3-substituted isocoumarins is described. The developed protocol allows convenient access to a range of synthetically useful 3-substituted isocoumarins and related fused heterocyclolactones in good to high yields, using silver tetrafluoroborate as the catalyst, and atmospheric oxygen

  描述了一种涉及银催化的有氧氧化/邻位-炔基苯甲醛的6-endo杂环化以产生 3-取代的异香豆素的方法。所开发的协议允许以良好至高产率方便地获得一系列合成有用的 3-取代异香豆素和相关的稠合杂环内酯，使用四氟硼酸银作为催化剂，大气氧作为终端氧化剂和内环氧的来源。机理研究表明自由基途径的参与。
• Transition-metal-free oxidative cyclization reaction of enynals to access pyrane-2-one derivatives
  作者：Farzaneh Ansari、Hormoz Khosravi、Alireza Abbasi Kejani、Mahsa Armaghan、Walter Frank、Saeed Balalaie、Farnaz Jafarpour

  DOI：10.1039/d1ob00726b

  日期：——

  α-pyrone derivatives via the formation of two C–O bonds. In this project, K2S2O8 has been introduced as an efficient oxygen source and C–H functionalization agent in regioselective oxidative cyclization reaction with a relatively broad substrate scope.

  开发了一种新颖且有效的烯醛无金属 C-H 官能化方法，通过形成两个 C-O 键来合成α-吡喃酮衍生物。在该项目中，K 2 S 2 O 8被引入作为区域选择性氧化环化反应中的有效氧源和C-H官能化剂，具有相对广泛的底物范围。
• One-pot synthesis of pyrano[4,3-b]quinolinones from 2-alkynyl-3-formylquinolines via oxidative 6-endo-dig ring closure
  作者：Priyabrata Roy、Binay K. Ghorai

  DOI：10.1016/j.tetlet.2011.11.016

  日期：2012.1

  regioselective one-pot procedure to synthesize pyranoquinolinones from readily available 2-alkynyl 3-formylquinolines under mild NaClO2/H2O2 conditions in good yields has been explored. This reaction sequence, involving oxidation followed by regioselective electrophilic 6-endo-dig cyclization is more efficient over the traditional Pd(0)-mediated synthesis. When scavenger-free conditions were used, unusual chlorinated

  一个新的区域选择性一个-一锅法合成pyranoquinolinones从容易获得的2-炔基-3- formylquinolines温和的NaClO下2 / H 2 ö 2以良好的收率的条件已探索。该反应顺序，涉及氧化随后区域选择性电6-内-挖环化是在传统的Pd（0）介导的合成更有效。当使用无清除剂的条件时，获得了不寻常的氯化呋喃喹啉酮衍生物。
• Metal-free POCl₃ promoted stereoselective hydrochlorination of ethynylated azaheterocycles
  作者：Ritush Kumar、Radhey M. Singh

  DOI：10.1039/c9ob00841a

  日期：——

  POCl3 as a chlorinating agent under metal-free reaction conditions. Mechanistic studies show that the reaction proceeded via nucleophilic attack of POCl3 on the nitrogen of the quinoline ring in a stereoselective manner. The resulting products were versatile intermediates in organic synthesis and were used in the cross-coupling reaction and metal-free synthesis of heterocycles. The developed protocol features

  使用POCl3作为无金属反应条件下的氯化剂，可实现乙炔氮杂杂环的有效盐酸盐化。机理研究表明，该反应是通过立体选择性的方式，通过POCl3对喹啉环氮的亲核攻击而进行的。所得产物是有机合成中的通用中间体，并用于杂环的交叉偶联反应和无金属合成中。所开发的方案具有廉价且易于合成的起始原料，易于操作，效率高和产物产率高的特点。
• TBHP-promoted oxidative cyclization of o-alkynylquinoline aldehydes: Metal/additive-free domino synthesis of pyrano[4,3-b]quinolin-1-ones
  作者：Jay Bahadur Singh、Kalpana Mishra、Tanu Gupta、Radhey M. Singh

  DOI：10.1016/j.tetlet.2018.01.083

  日期：2018.3

  TBHP-promoted domino synthesis of pyrano[4,3-b]quinolin-1-ones is described from o-alkynylquinoline aldehydes. The radical reaction proceeded without metal and additive via oxidation of aldehydic C-H bond into C-OH bond followed by intramolecular 6-endo-dig cyclization. The probable mechanism is discussed.

  由邻炔基喹啉醛描述了TBHP促进的吡喃并[4,3 - b ]喹啉-1-酮的多米诺合成。自由基反应是在没有金属和添加剂的情况下进行的，方法是将醛键的CH键氧化为C-OH键，然后进行分子内6-内切环化。讨论了可能的机制。