2-phenyl-5H-indeno<1,2-b>pyridin-5-one | 69751-56-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-phenyl-5H-indeno<1,2-b>pyridin-5-one
• 英文别名: 2-phenyl-5H-indeno[1,2-b]pyridin-5-one；3-Phenyl-4-azafluorenone；2-phenyl-indeno[1,2-b]pyridin-5-one；2-Phenyl-indeno[1,2-b]pyridin-5-on；2-phenylindeno[1,2-b]pyridin-5-one
• CAS: 69751-56-0
• 化学式: C₁₈H₁₁NO
• 分子量: 257.291
• InChiKey: JZPIBOXXNYUTAL-UHFFFAOYSA-N

物化性质

• 熔点：
  148-150 °C
• 沸点：
  468.1±24.0 °C(Predicted)
• 密度：
  1.265±0.06 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：
  1
• 环数：
  4.0
• 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

• 作为产物：
  描述：

  3-Phenyl-9-benzylidene-4-azafluorene 在 potassium permanganate 作用下， 以 丙酮 为溶剂， 以44%的产率得到2-phenyl-5H-indeno<1,2-b>pyridin-5-one
  参考文献：
  名称：

  Synthesis and some properties of substituted 4-azafluorenes

  摘要：

  DOI：

  10.1007/bf00509710

文献信息

• Synthesis of substituted azafluorenones from dihalogeno diaryl ketones by palladium-catalyzed auto-tandem processes
  作者：Nada Marquise、Vincent Dorcet、Floris Chevallier、Florence Mongin

  DOI：10.1039/c4ob01629g

  日期：——

  Substituted azafluorenones were synthesized from different dihalogeno diaryl ketones under palladium catalysis by combining either Suzuki or Heck coupling with direct cyclizing arylation. Conditions were identified to allow both auto-tandem processes to proceed successfully from 3-(bromobenzoyl)- or 3-benzoyl-4-bromo-2-chloropyridines, as well as 4-benzoyl-2,3- and 4-benzoyl-2,5-dichloropyridines.

  通过将Suzuki或Heck偶合与直接环化芳基化反应相结合，在钯催化下，由不同的二卤代二芳基酮合成了取代的氮杂芴酮。确定条件以使自动串联过程能够成功地由3-（溴苯甲酰基）-或3-苯甲酰基-4-溴-2-氯吡啶以及4-苯甲酰基-2,3-和4-苯甲酰基-2成功进行，5-二氯吡啶。
• 4-Azafluorenone and α-Carboline Fluorophores with Green and Violet/Blue Emission
  作者：Marek Cigáň、Peter Danko、Henrich Brath、Matúš Čakurda、Roman Fišera、Jana Donovalová、Juraj Filo、Martin Weis、Ján Jakabovič、Miroslav Novota、Anton Gáplovský

  DOI：10.3390/molecules24132378

  日期：——

  The emission properties of three 4-azafluorenone and five new α-carboline fluorophores in both solution and thin solid films were investigated. Fluorescence of the azafluorenone is clearly enhanced in thin solid films due to the presence of phenyl/biphenyl rotors, and these derivatives can be classified as green Aggregation-Induced Emission luminogens (AIEgens) with a non-emissive heteroaromatic core structure. Compared to azafluorenones, emission of α-carbolines is hypsochromically shifted to the blue region of the electromagnetic spectrum, and most of these derivatives exhibit strong violet-blue fluorescence in both solution and thin solid film layers. Further, the effective mobility and electroluminescence of new α-carbolines were investigated in prepared organic field-effect transistors and organic light-emitting diodes, respectively.

  研究了三种4-azafluorenone和五种新的α-咔啉荧光物质在溶液和薄膜中的发射特性。由于存在苯/联苯转子，azafluorenone在薄膜中的荧光明显增强，这些衍生物可以被归类为绿色聚集诱导发光物质（AIEgens），具有非发光的杂芳核心结构。与azafluorenones相比，α-咔啉的发射向电磁光谱的蓝区移动，大多数这些衍生物在溶液和薄膜层中表现出强烈的紫蓝色荧光。此外，还研究了新的α-咔啉在制备的有机场效应晶体管和有机发光二极管中的有效迁移率和电致发光性能。
• Synthesis of Functionalized Pyridines via Cu(II)-Catalyzed One-Pot Cascade Reactions of Inactivated Saturated Ketones with Electron-Deficient Enamines
  作者：Guang Chen、Ze Wang、Xinying Zhang、Xuesen Fan

  DOI：10.1021/acs.joc.7b01901

  日期：2017.10.20

  In this paper, a novel and efficient synthesis of 3-acylpyridines and pyridine-3-carboxylates through the oxidative one-pot sequential reactions of inactivated saturated ketones with electron-deficient enamines is presented. Mechanistically, the formation of the title compounds involves the in situ formation of an enone intermediate through an oxidative dehydrogenation of the saturated ketone substrate

  在本文中，提出了一种新的有效的合成方法，该方法通过灭活的饱和酮与缺电子的烯胺的氧化一锅顺序反应来合成3-酰基吡啶和-3-羧酸吡啶酯。从机理上讲，标题化合物的形成涉及通过饱和酮底物的氧化脱氢原位形成烯酮中间体，然后通过级联过程用β-烯胺酮或β-烯胺酸酯将其[3 + 3]环合，包括迈克尔加成，醛醇缩合和氧化芳构化。
• Doebner; Kuntze, Justus Liebigs Annalen der Chemie, 1888, vol. 249, p. 133
  作者：Doebner、Kuntze

  DOI：——

  日期：——
• Nitta, Makoto; Ohnuma, Manami; Iino, Yukio, Journal of the Chemical Society. Perkin transactions I, 1991, # 5, p. 1115 - 1118
  作者：Nitta, Makoto、Ohnuma, Manami、Iino, Yukio

  DOI：——

  日期：——