1-<2-<<2-(Diethylamino)ethyl>amino>-4-(2-methyl-1,3-dioxan-2-yl)-3-pyridyl>ethanone | 137742-03-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-<2-<<2-(Diethylamino)ethyl>amino>-4-(2-methyl-1,3-dioxan-2-yl)-3-pyridyl>ethanone
• 英文别名: 1-[2-[2-(diethylamino)ethylamino]-4-(2-methyl-1,3-dioxan-2-yl)pyridin-3-yl]ethanone
• CAS: 137742-03-1
• 化学式: C₁₈H₂₉N₃O₃
• 分子量: 335.447
• InChiKey: KICGULSTDKAMRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  63.69
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  1-(2-氟-4-吡啶基)乙醇 在 manganese(IV) oxide 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 甲苯 为溶剂， 反应 75.0h， 生成 1-<2-<<2-(Diethylamino)ethyl>amino>-4-(2-methyl-1,3-dioxan-2-yl)-3-pyridyl>ethanone
  参考文献：
  名称：

  A new convergent route to 1-substituted ellipticines

  摘要：

  1-(2-Fluoro-4-pyridyl)ethanone was synthesized from 2-fluoropyridine and was ortho-lithiated after activation as the propylene glycol ketal. The resulting 3-lithio derivative was trapped by various electrophiles but reacted in low yield with N-protected 3-indolecarbaldehyde. Model compounds 1-[[[2-(diethylamino)ethyl]amino]-3-pyridyl]ethanol and -ethanone were prepared and selectively condensed with indole. 1-[[[2-(Diethylamino)-ethyl]amino]-3-pyridyl]ethanol and -ethanone bearing a ketal-protected acetyl moiety at the C-4 position have been obtained in high yields starting from the propylene glycol ketal of 1-(2-fluoro-4-pyridyl)ethanone. These reagents could not be condensed with indole either due to side reactions between the C-3 and C-4 functions or to steric hindrance. 1-(2-Substituted-4-bromo-3-pyridyl)ethanols were synthesized via a metalation/halogen-dance strategy starting from 2-fluoropyridine. 1-(2,4-Dihalo-3-pyridyl)-1-chloroethane could be prepared and condensed with 1-indolylmagnesium iodide, which allowed the construction of the expected 3-[1-(3-pyridyl)ethyl]indole skeleton. Functionalization of the pyridine C-4 bromo position was achieved by a vinylstannane cross-coupling reaction using a palladium(0) catalyst. Acidic treatment of the resulting 4-(1-ethoxyethenyl)pyridine led to 1-fluoroellipticine. The whole sequence requires six steps from indole and 2-fluoropyridine and allows an attractive overall yield.

  DOI：

  10.1021/jo00028a032