3H-pyrano[3,2-f]quinolin-3-one | 4959-99-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3H-pyrano[3,2-f]quinolin-3-one
• 英文别名: 3H-pyrano[3,2-f]quinoline-3-one；3-H-Pyrano<3,2-f>chinolin-3-on；pyrido[3,2-f]coumarin；pyrano[3,2-f]quinolin-3-one；Pyrano[3,2-f]chinolin-3-on；3H-Pyrano(3,2-f)quinolin-3-one；pyrano[3,2-f]quinolin-3-one
• CAS: 4959-99-3
• 化学式: C₁₂H₇NO₂
• 分子量: 197.193
• InChiKey: ROVZMKXAGDXPJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• 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

• 作为反应物：
  描述：

  3H-pyrano[3,2-f]quinolin-3-one 在 sodium sulfite 作用下， 生成 trans-β-(6-oxy-quinolyl-(5))-acrylic acid
  参考文献：
  名称：

  Dey; Row, Journal of the Chemical Society, 1924, vol. 125, p. 561

  摘要：

  DOI：
• 作为产物：
  描述：

  6-羟基喹啉 在 sodium hydroxide 、 乙醇 、 sodium acetate 作用下， 生成 3H-pyrano[3,2-f]quinolin-3-one
  参考文献：
  名称：

  Bobranski, Journal fur praktische Chemie (Leipzig 1954), 1932, vol. <2> 134, p. 153,155

  摘要：

  DOI：

文献信息

• Regioselective Synthesis of Annulated Quinoline and Pyridine Derivatives by Silver-Catalyzed 6-endo-dig Cycloisomerization
  作者：K. Majumdar、Raj Nandi、Sintu Ganai、Abu Taher

  DOI：10.1055/s-0030-1259097

  日期：2011.1

  3H-pyrano[3,2-f]quinoline-3-one, 4-methyl-4,7-phen­anthrolin-3(4H)-one, and 1,3-dimethylpyrido[3,2-d]pyrimidine-2,4(1H,3H)-dione derivatives have been synthesized by hitherto unreported silver-catalyzed 6-endo-dig mode of cycloisomerization from various N-propargylated heterocyclic compounds. The silver-catalyzed reaction provides the synthesis of potential bioactive compounds in excellent yields.

  3H-吡喃并[3,2-f]喹啉-3-酮、4-甲基-4,7-二氢吩噻啉-3(4H)-酮和1,3-二甲基吡啶并[3,2-d]嘧啶-2,4(1H,3H)-二酮衍生物已经通过迄今未报道的银催化的6-endo-dig模式的环异构化反应从各种N-炔丙基化的杂环化合物中合成。这种银催化的反应为合成潜在的生物活性化合物提供了极佳的产率。
• Electrocyclization of cis-dienals in organic synthesis: a new and versatile synthetic method for the preparation of aryl- and heteroaryl-fused coumarins
  作者：Yung-Son Hon、Tze-Wei Tseng、Chia-Yi Cheng

  DOI：10.1039/b912887e

  日期：——

  Benzo-, furo-, thieno-, and pyrido[f]coumarins were prepared by generating the 2H-pyran-2-one moieties from the oxidation of the corresponding 2H-pyran rings, which were formed in situ from the electrocyclization of cis-dienals.

  通过从相应的2H-吡喃环的氧化反应生成2H-吡喃-2-酮部分来制备苯并，呋喃-，噻吩并-和吡啶并[f]香豆素，它们是由顺式C-环的电环化而形成的。日记。
• Synthesis of quinolines and fused pyridocoumarins from N-propargylanilines or propargylaminocoumarins by catalysis with gold nanoparticles supported on TiO2
  作者：Theodoros S. Symeonidis、Ioannis N. Lykakis、Konstantinos E. Litinas

  DOI：10.1016/j.tet.2013.04.026

  日期：2013.6

  [5,6]-Fused pyridocoumarins are prepared under mild conditions in excellent yields through the activation of the triple bond of 6-propargylaminocoumarins by gold nanoparticles supported on TiO2. The analogous reaction of N-propargylanilines with Au/TiO2 or Au/Al2O3 resulted in the formation of quinolines.

  [5,6]-吡啶并香豆素是在温和的条件下通过负载在TiO 2上的金纳米粒子活化6-炔丙基氨基香豆素的三键而以极好的收率制备的。N-炔丙基苯胺与Au / TiO 2或Au / Al 2 O 3的类似反应导致喹啉的形成。
• Synthesis of [5,6]-fused pyridocoumarins through aza-Claisen rearrangement of 6-propargylaminocoumarins
  作者：Theodoros S. Symeonidis、Michael G. Kallitsakis、Konstantinos E. Litinas

  DOI：10.1016/j.tetlet.2011.08.012

  日期：2011.10

  [5,6]-Fused pyridocoumarins are prepared through aza-Claisen rearrangement and subsequent in situ cyclization of 6-propargylaminocoumarins under microwave irradiation in the presence of boron trifluoride diethyl etherate in N,N-dimethylformamide. During this process demethoxycarbonylation is observed in the corresponding 4-carbomethoxycoumarin derivatives. (C) 2011 Elsevier Ltd. All rights reserved.
• Rapid decoloration and acidichromism of photochromic 3,3-diaryl-3H-pyrano[3,2-f]quinolines
  作者：Bin Li、Zipei Sun、Yan Zhai、Jianlan Jiang、Yaodong Huang、Jiben Meng

  DOI：10.1016/j.tet.2019.130471

  日期：2019.9

  Pyranoquinoline, with its light-sensitive fragment and coordination node, provides an ideal matrix for the development of multi-functional photochromic compounds. This paper presents the synthesis and photochromic properties of 3,3-diaryl-3H-pyrano[3,2-f]quinoline derivatives QP1-QP8. All exhibited good photochromism under UV light irradiation followed by biexponential kinetic decay in the dark at ambient temperature. Their photochromic processes were reversible, and acidichromism was observed to occur in solution. The fading speeds of QP2 and QP6 were higher than those of their known naphthopyran counterparts, whereas the decoloring speeds of the six other compounds were all over an order of magnitude higher than those of QP2 and QP6. The synthesized pyranoquinolines exhibited very good fatigue resistance both in solution and the solid state. Compared to other pyranoquinolines, the optical densities of QP2 and QP6, i.e., the compounds with 2,4-dimethoxylphenyl and 1-naphthyl, were enhanced dramatically. For all the synthesized pyranoquinolines, a distinct bathochromic shift was observed with increasing solvent polarity. The structure-property relationship of the pyranoquinolines was revealed through the single-crystal X-ray analysis of QP1 and QP7. (C) 2019 Elsevier Ltd. All rights reserved.