N,N-Diethyl-4-(3-pyridinecarbonyl)-3-pyridinecarboxamide | 77924-14-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N,N-Diethyl-4-(3-pyridinecarbonyl)-3-pyridinecarboxamide
• 英文别名: N,N-diethyl-4-(3-pyridylcarbonyl)nicotinamide；N,N-Diethyl-4-nicotinoylnicotinamide；N,N-diethyl-4-nicotinoyl-nicotinamide；N,N-diethyl-4-(pyridine-3-carbonyl)pyridine-3-carboxamide
• CAS: 77924-14-2
• 化学式: C₁₆H₁₇N₃O₂
• 分子量: 283.33
• InChiKey: OWVFXKIQZDPNKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  517.6±40.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-Diethyl-4-(3-pyridinecarbonyl)-3-pyridinecarboxamide 在 一水合肼 作用下， 以 二乙二醇 为溶剂， 以96%的产率得到1-(3-Pyridyl)pyrido<3,4-d>pyridazin-4(3H)-one
  参考文献：
  名称：

  Application of organolithium and related reagents in synthesis, Part XII. Synthesis of phenyl- and pyridylpyridopyridazinones and their derivatives

  摘要：

  The preparation of the pyridazinones 10a, 10b, 11a, 11b, and 12a, 12b from the ketoamides 7,8, and 9 and hydrazine hydrate is described. It was found that from ketoamides 8b and 9b in addition to the expected pyridopyridazinones 11b and 12b also aminopyridopyridazines 14 and 15 were formed and that ketoamide 7b gave exclusively aminopyridopyridazine 13. The pyridopyridazinones 10b, 11b, and 12b were alkylated with alkyl iodides.

  DOI：

  10.1007/bf00819523
• 作为产物：
  描述：

  尼可刹米 在 lithium diisopropyl amide 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以68%的产率得到N,N-Diethyl-4-(3-pyridinecarbonyl)-3-pyridinecarboxamide
  参考文献：
  名称：

  N，N-二烷基吡啶基羧酸酰胺与酰胺化锂的反应。N，N-二异丙基吡啶基羧酸酰胺的区域选择性锂化，一种合成2,3-和3,4-二取代吡啶的有用方法

  摘要：

  N，N-二甲基-，N，N-二乙基-和N，N-二异丙基吡啶基羧酸酰胺在与Et 2 NLi和iPr 2 NLi的反应中的行为，以及合成2,3-和3的简便方法，描述了通过N，N-二异丙基酰胺的直接锂化导致随后的邻位新的CC键形成的4-二取代的吡啶。

  DOI：

  10.1016/0040-4039(80)88108-1

文献信息

• Synthesis of (±)-sesbanine via directed metalation of tertiary nicotinamides
  作者：Masatomo Iwao、Tsukasa Kuraishi

  DOI：10.1016/s0040-4039(00)87968-x

  日期：——

  Racemic sesbanine was synthesized by using regioselective ortho lithiation of N,N-dialkylnicotinamides and subsequent condensation with 3-cyclopentenone as key reactions.

  通过使用N，N-二烷基烟酰胺的区域选择性邻位锂化反应以及随后与3-环戊烯酮的缩合反应为关键反应，合成了外消旋的塞斯班宁。
• Epsztajn, Jan; Brzezinski, Jacek Z.; Jozwiak, Andrzej, Journal of Chemical Research, Miniprint, 1986, # 1, p. 401 - 441
  作者：Epsztajn, Jan、Brzezinski, Jacek Z.、Jozwiak, Andrzej

  DOI：——

  日期：——
• EPSZTAJN, J.;BRZEZINSKI, J. Z.;JOZWIAK, A., J. CHEM. RES. SYNOP., 1986, N 1, 18-19
  作者：EPSZTAJN, J.、BRZEZINSKI, J. Z.、JOZWIAK, A.

  DOI：——

  日期：——
• Reactions of the N,N-dialkylpyridylcarboxylic amides with lithium amides. Regioselective lithiation of N,N-diisopropylpyridylcarboxylic amides, a useful method for synthesis of 2,3- and 3,4-disubstituted pyridines
  作者：Jan Epsztajn、Zbigniew Berski、Jacek Z. Brzeziński、Andrzej Jóźwiak

  DOI：10.1016/0040-4039(80)88108-1

  日期：1980.1

  The behaviour of the N,N-dimethyl-, N,N-diethyl- and N,N-diisopropylpyridylcarboxylic amides in the reactions with Et2NLi and iPr2NLi, and a convenient way of synthesis of 2,3- and 3,4-disubstituted pyridines, by the direct lithiation of N,N-diisopropylamides leading subsequently to the ortho new CC bonds formation, are described.

  N，N-二甲基-，N，N-二乙基-和N，N-二异丙基吡啶基羧酸酰胺在与Et 2 NLi和iPr 2 NLi的反应中的行为，以及合成2,3-和3的简便方法，描述了通过N，N-二异丙基酰胺的直接锂化导致随后的邻位新的CC键形成的4-二取代的吡啶。
• Application of organolithium and related reagents in synthesis, Part XII. Synthesis of phenyl- and pyridylpyridopyridazinones and their derivatives
  作者：J. Epsztajn、J. Z. Brzeziński、K. Czech

  DOI：10.1007/bf00819523

  日期：1993.5

  The preparation of the pyridazinones 10a, 10b, 11a, 11b, and 12a, 12b from the ketoamides 7,8, and 9 and hydrazine hydrate is described. It was found that from ketoamides 8b and 9b in addition to the expected pyridopyridazinones 11b and 12b also aminopyridopyridazines 14 and 15 were formed and that ketoamide 7b gave exclusively aminopyridopyridazine 13. The pyridopyridazinones 10b, 11b, and 12b were alkylated with alkyl iodides.