6-ethoxycarbonylmethyl-5,6-dihydro-5-methylphenanthridine

• 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: 6-ethoxycarbonylmethyl-5,6-dihydro-5-methylphenanthridine
• 英文别名: ethyl 2-(5-methyl-6H-phenanthridin-6-yl)acetate
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: OCVYFLXHZVBTEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (三甲基硅基)乙酸乙酯 、 N-methyl phenanthridinium iodide 在 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以77%的产率得到6-ethoxycarbonylmethyl-5,6-dihydro-5-methylphenanthridine
  参考文献：
  名称：

  Silicon-Assisted Ethoxycarbonylmethylation ofN-Methylquinolinium and Isoquinolinium Iodides

  摘要：

  A new regioselective route to 2-ethoxycarbonylmethyl- 1,2-dihydro-N-methylquinolines and 1-ethoxycarbonylmethyl-1,2-dihydro-N-methylisoquinolines is described starting from methylquinolinium or -isoquinolinium iodides and commercially available ethyltrimethylsilyl acetate (ETSA). The methylene carbanion was generated by fluorodesilylation using caesium fluoride. On exposure to air, the ethoxycarbonylmethyl adducts were oxidised, leading to the corresponding alkylidene derivatives 4 and 5, whereas 2a in solution led slowly to its regioisomer 6a.

  DOI：

  10.1002/1099-0690(200008)2000:16<2915::aid-ejoc2915>3.0.co;2-b

文献信息

• Silicon-Assisted Ethoxycarbonylmethylation ofN-Methylquinolinium and Isoquinolinium Iodides
  作者：Faïza Diaba、Cyril Le Houerou、Micheline Grignon-Dubois、Bernadette Rezzonico、Pierre Gerval

  DOI：10.1002/1099-0690(200008)2000:16<2915::aid-ejoc2915>3.0.co;2-b

  日期：2000.8

  A new regioselective route to 2-ethoxycarbonylmethyl- 1,2-dihydro-N-methylquinolines and 1-ethoxycarbonylmethyl-1,2-dihydro-N-methylisoquinolines is described starting from methylquinolinium or -isoquinolinium iodides and commercially available ethyltrimethylsilyl acetate (ETSA). The methylene carbanion was generated by fluorodesilylation using caesium fluoride. On exposure to air, the ethoxycarbonylmethyl adducts were oxidised, leading to the corresponding alkylidene derivatives 4 and 5, whereas 2a in solution led slowly to its regioisomer 6a.