4-(4-nitrophenyl)-1-tosyl-1,4-dihydroquinoline | 1372125-93-3

• 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: 4-(4-nitrophenyl)-1-tosyl-1,4-dihydroquinoline
• CAS: 1372125-93-3
• 化学式: C₂₂H₁₈N₂O₄S
• 分子量: 406.462
• InChiKey: GNDZXMCLYDDDKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  80.52
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(4-nitrophenyl)-1-tosyl-1,4-dihydroquinoline 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以87%的产率得到4-(4-nitrophenyl)quinoline
  参考文献：
  名称：

  Synthesis of Quinolines from N-Tosyl-1-azadienes

  摘要：

  A route to aryl-substituted quinolines from N-tosyl 1-azadienes is described. The key steps are a [4+2] cycloaddition with benzyne followed by base treatment of the 1,4-dihydroquinoline product. The N-tosyl 1-azadienes were prepared from readily accessible cinnamaldehyde and chalcone substrates by condensation with p-TsNH2. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.726388
• 作为产物：
  描述：

  对硝基肉桂醛 在 三氟化硼乙醚 、 亚硝酸异戊酯 、 三氯乙酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 4.0h， 生成 4-(4-nitrophenyl)-1-tosyl-1,4-dihydroquinoline
  参考文献：
  名称：

  Synthesis of Quinolines from N-Tosyl-1-azadienes

  摘要：

  A route to aryl-substituted quinolines from N-tosyl 1-azadienes is described. The key steps are a [4+2] cycloaddition with benzyne followed by base treatment of the 1,4-dihydroquinoline product. The N-tosyl 1-azadienes were prepared from readily accessible cinnamaldehyde and chalcone substrates by condensation with p-TsNH2. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.726388

文献信息

• Synthesis of Aryl-Substituted 1,4-Dihydroquinolines by [4+2] Cycloaddition of Benzyne with 1-Azadienes
  作者：Keith Mead、Sean Stokes、Markondaiah Bekkam、Madeline Rupp

  DOI：10.1055/s-0031-1290137

  日期：2012.2

  The synthesis of aryl-substituted 1,4-dihydroquinolines can be achieved using a [4+2] cycloaddition between benzyne and various aryl-substituted 1-azadienes. The conditions are tolerated by N-aryl-, alkyl-, tosyl-, and tert-butoxycarbonyl-protected 1-azadienes. A short synthesis of the fungal metabolite 3-O-methylviri­dicatin is reported. benzyne - dihydroquinolines - azadienes - cycloaddition - 3

  芳基取代的1，4-二氢喹啉的合成可以使用苯并炔和各种芳基取代的1-氮二烯之间的[4 + 2]环加成反应来实现。N-芳基- ，烷基-，甲苯磺酰基-和叔丁氧羰基保护的1-氮杂二烯可耐受这些条件。据报道，真菌代谢物3- O-甲基病毒素的合成很短。 苯并-二氢喹啉-氮杂二氮-环加成-3- O-甲基viridicatin