2-(2'-aminophenyl)quinolin-4-one

• 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-(2'-aminophenyl)quinolin-4-one
• 英文别名: 2-(2-aminophenyl)quinolin-4(1H)-one；2-(2-aminophenyl)-1H-quinolin-4-one
• 化学式: C₁₅H₁₂N₂O
• 分子量: 236.273
• InChiKey: LOHFLVZZBGNYTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2'-aminophenyl)quinolin-4-one 、 N-叔丁氧羰基-4-哌啶酮 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以86 mg的产率得到t-butyl 7-oxo-7,12-dihydro-5H-spiro[dibenzo[b,h][1,6]naphthyridine-6,4'-piperidine]-1'-carboxylate
  参考文献：
  名称：

  Dibenzonaphthyridinones: Heterocycle-to-Heterocycle Synthetic Strategies and Photophysical Studies

  摘要：

  A heterocycle-to-heterocycle strategy is presented for the preparation of highly fluorescent and solvatochromic dibenzonaphthyridinones (DBNs) via methodology that leads to the formation of a tertiary, spiro-fused carbon center. A linear correlation between the results of photophysical experiments and time dependent density functional theory calculations was observed for the lambda(max) of excitation for DBNs with varying electronic character.

  DOI：

  10.1021/acs.orglett.5b02680
• 作为产物：
  描述：

  1-乙炔基-2-硝基苯 在 铁粉 、 sodium hydride 、 氯化铵 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 0.8h， 生成 2-(2'-aminophenyl)quinolin-4-one
  参考文献：
  名称：

  杂环-杂环策略：4-氨基喹啉、1H-吲哚和喹啉-4（1H）-酮的（2-硝基苯基）异恶唑前体

  摘要：

  据报道，还原性杂环 - 杂环（杂环 → 杂环；H–H）转化为 4-氨基喹啉、3-酰基吲哚和喹啉-4（1 H）-从 2-硝基苯基取代的异恶唑转化。当此方法应用于 3,5-、4,5- 和 3,4-双（2-硝基苯基）异恶唑时，化学选择性杂环化会专门生成喹啉-4（1 H）-酮和 4-氨基喹啉。

  DOI：

  10.1021/ol400787y

文献信息

• Heterocycle–Heterocycle Strategies: (2-Nitrophenyl)isoxazole Precursors to 4-Aminoquinolines, 1<i>H</i>-Indoles, and Quinolin-4(1<i>H</i>)-ones
  作者：Keith C. Coffman、Teresa A. Palazzo、Timothy P. Hartley、James C. Fettinger、Dean J. Tantillo、Mark J. Kurth

  DOI：10.1021/ol400787y

  日期：2013.4.19

  Reductive heterocycle–heterocycle (heterocycle → heterocycle; H–H) transformations that give 4-aminoquinolines, 3-acylindoles, and quinolin-4(1H)-ones from 2-nitrophenyl substituted isoxazoles are reported. When this methodology is applied to 3,5-, 4,5-, and 3,4-bis(2-nitrophenyl)isoxazoles, chemoselective heterocyclization gives quinolin-4(1H)-ones, and 4-aminoquinolines, exclusively.

  据报道，还原性杂环 - 杂环（杂环 → 杂环；H–H）转化为 4-氨基喹啉、3-酰基吲哚和喹啉-4（1 H）-从 2-硝基苯基取代的异恶唑转化。当此方法应用于 3,5-、4,5- 和 3,4-双（2-硝基苯基）异恶唑时，化学选择性杂环化会专门生成喹啉-4（1 H）-酮和 4-氨基喹啉。
• Remarkably Efficient and Direct Route to Quinolines and Benzoazepines from the Condensation of Benzoxazinediones with Phosphonium Carbanion Salts
  作者：Wafaa M. Abdou、Azza A. Kamel

  DOI：10.1080/00397910701572670

  日期：2007.11

  Treatment of 2H-3,1-benzoxazine-2,4(1H)-dione (1a) with vinyltriphenyl-phosphonium bromide (2a) gives substituted benzoazepine 8a (48% yield) and indolizinone 12 (27% yield), whereas substituted quinolinone 15 and benzoazepine 8b were isolated from the reaction of N-methylisatoic anhydride (1b) and 2a. Furthermore, a series of quinoline derivatives was synthesized from the reactions of la and 1b with allyl-(2b), alkyl-(2c), (2d), and cyanomethyl-(3) triphenylphosphonium salts.
• Dibenzonaphthyridinones: Heterocycle-to-Heterocycle Synthetic Strategies and Photophysical Studies
  作者：Teresa A. Palazzo、Digambara Patra、Joung S. Yang、Elsy El Khoury、Mackenzie G. Appleton、Makhluf J. Haddadin、Dean J. Tantillo、Mark J. Kurth

  DOI：10.1021/acs.orglett.5b02680

  日期：2015.12.4

  A heterocycle-to-heterocycle strategy is presented for the preparation of highly fluorescent and solvatochromic dibenzonaphthyridinones (DBNs) via methodology that leads to the formation of a tertiary, spiro-fused carbon center. A linear correlation between the results of photophysical experiments and time dependent density functional theory calculations was observed for the lambda(max) of excitation for DBNs with varying electronic character.