2-(5-乙基-2-呋喃基)-3-甲氧基甲基喹啉 | 442682-51-1

• 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
• 中文名称: 2-(5-乙基-2-呋喃基)-3-甲氧基甲基喹啉
• 英文名称: 2-(5-ethyl-2-furyl)-3-methoxymethylquinoline
• 英文别名: 2-(5-Ethylfuran-2-yl)-3-(methoxymethyl)quinoline
• CAS: 442682-51-1
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: ZIKNPLNRJYELPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(5-乙基-2-呋喃基)-3-甲氧基甲基喹啉 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 碳酸氢钠 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 水 、 丙酮 为溶剂， 反应 29.0h， 生成 麦皮星酮
  参考文献：
  名称：

  2-Pyridones from Cyanoacetamides and Enecarbonyl Compounds:  Application to the Synthesis of Nothapodytine B

  摘要：

  The condensation of an enone or enal with cyanoacetamide derivatives and t-BuOK furnishes either 3-eyano-2-pyridones or 3-unsubstituted-2-pyridones, depending on whether the reaction is carried out in the presence or in the absence Of O-2. In the first case, in situ oxidation of Michael-type intermediates takes place; in the second case, the products result from "decyanidative aromatization" of such intermediates. A one-step synthesis of 3-alkyl-2-pyridones has been devised on the basis of decyanative union of an enone/enal and a 2-alkyleyanoacetamide. The new reaction forms the centerpiece of an unusually concise synthesis of nothapodytine B (mappicine ketone).

  DOI：

  10.1021/jo025546d
• 作为产物：
  描述：

  2-乙基呋喃 在 四(三苯基膦)钯 barium dihydroxide 、 正丁基锂 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 反应 13.0h， 生成 2-(5-乙基-2-呋喃基)-3-甲氧基甲基喹啉
  参考文献：
  名称：

  2-Pyridones from Cyanoacetamides and Enecarbonyl Compounds:  Application to the Synthesis of Nothapodytine B

  摘要：

  The condensation of an enone or enal with cyanoacetamide derivatives and t-BuOK furnishes either 3-eyano-2-pyridones or 3-unsubstituted-2-pyridones, depending on whether the reaction is carried out in the presence or in the absence Of O-2. In the first case, in situ oxidation of Michael-type intermediates takes place; in the second case, the products result from "decyanidative aromatization" of such intermediates. A one-step synthesis of 3-alkyl-2-pyridones has been devised on the basis of decyanative union of an enone/enal and a 2-alkyleyanoacetamide. The new reaction forms the centerpiece of an unusually concise synthesis of nothapodytine B (mappicine ketone).

  DOI：

  10.1021/jo025546d

文献信息

• 2-Pyridones from Cyanoacetamides and Enecarbonyl Compounds:  Application to the Synthesis of Nothapodytine B
  作者：Lionel Carles、Kesavaram Narkunan、Sébastien Penlou、Laurence Rousset、Denis Bouchu、Marco A. Ciufolini

  DOI：10.1021/jo025546d

  日期：2002.6.1

  The condensation of an enone or enal with cyanoacetamide derivatives and t-BuOK furnishes either 3-eyano-2-pyridones or 3-unsubstituted-2-pyridones, depending on whether the reaction is carried out in the presence or in the absence Of O-2. In the first case, in situ oxidation of Michael-type intermediates takes place; in the second case, the products result from "decyanidative aromatization" of such intermediates. A one-step synthesis of 3-alkyl-2-pyridones has been devised on the basis of decyanative union of an enone/enal and a 2-alkyleyanoacetamide. The new reaction forms the centerpiece of an unusually concise synthesis of nothapodytine B (mappicine ketone).