3,4-dimethoxy-3,3-dimethyl-3,4-dihydro-2H-acridin-1-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: 3,4-dimethoxy-3,3-dimethyl-3,4-dihydro-2H-acridin-1-one
• 英文别名: 6,7-Dimethoxy-3,3-dimethyl-2,4-dihydroacridin-1-one
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: MXWFFNQFUHWMAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-硝基藜芦醛 在 哌啶 、 sodium sulfide 作用下， 以 乙醇 为溶剂， 反应 14.17h， 生成 3,4-dimethoxy-3,3-dimethyl-3,4-dihydro-2H-acridin-1-one
  参考文献：
  名称：

  A Novel Traceless Solid-Phase Friedländer Synthesis

  摘要：

  graphicA new solid-phase synthesis of quinolines based on a Friedlander-type reaction between the resin-bound azomethine 1b and ketones 2 is described. This cyclative cleavage approach affords quinolines 3a-f in 50-81% yields. The polymer-bound aniline equivalent is easily recycled and may be reused with comparable performance.

  DOI：

  10.1021/ol035049z

文献信息

• Synthesis of quinolines via copper-catalyzed domino reactions of enaminones
  作者：Benyapa Kaewmee、Vatcharin Rukachaisirikul、Juthanat Kaeobamrung

  DOI：10.1039/c7ob01867c

  日期：——

  Quinoline derivatives were obtained from enaminones and 2-bromo- or 2-iodobenzaldehydes via copper-catalyzed domino reactions consisting of the Aldol reaction, C(aryl)-N bond formation and elimination. The electronic effect of aldehydes played a major role in the reaction outcome. Two simple protocols are disclosed to achieve variuos quinolines from both cyclic and acyclic enaminones in good yields

  喹啉衍生物是通过铜催化的由Aldol反应，C（芳基）-N键的形成和消除组成的多米诺反应从烯胺酮和2-溴-或2-碘代苯甲醛中获得的。醛的电子效应在反应结果中起主要作用。公开了两种简单的方案以良好的收率从环状和无环烯胺酮两者获得变异喹啉。对于反应性较低的无环烯胺酮，表明2-（2-溴苄叉基）丙二酸二乙酯比苯甲醛更具相容性。
• A Novel Traceless Solid-Phase Friedländer Synthesis
  作者：Claudine Patteux、Vincent Levacher、Georges Dupas

  DOI：10.1021/ol035049z

  日期：2003.8.1

  graphicA new solid-phase synthesis of quinolines based on a Friedlander-type reaction between the resin-bound azomethine 1b and ketones 2 is described. This cyclative cleavage approach affords quinolines 3a-f in 50-81% yields. The polymer-bound aniline equivalent is easily recycled and may be reused with comparable performance.