7-(Acetylamino)-3-carbethoxy-1,8-naphthyridin-(1H)2-one | 151510-27-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 7-(Acetylamino)-3-carbethoxy-1,8-naphthyridin-(1H)2-one
• 英文别名: naphthyridone；ethyl 7-acetamido-2-oxo-1H-1,8-naphthyridine-3-carboxylate
• CAS: 151510-27-9
• 化学式: C₁₃H₁₃N₃O₄
• 分子量: 275.264
• InChiKey: VDURTAMYXKLNKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  101.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  7-(Acetylamino)-3-carbethoxy-1,8-naphthyridin-(1H)2-one 在 三氯氧磷 作用下， 反应 13.0h， 以57%的产率得到Ethyl 7-(acetylamino)-2-chloro-1,8-naphthyridine-3-carboxylate
  参考文献：
  名称：

  Convenient synthesis of 2-amino-1,8-naphthyridines, building blocks for host-guest and self-assembling systems

  摘要：

  Application of the Reimer-Tiemann reaction to 2,6-diaminopyridine afforded a 26% yield of 2,6-diaminopyridine-3-carboxaldehyde (4) and a small amount (4%) of 2,6-diaminopyridine-3,5-dicarboxaldehyde. Alternatively, conversion of 2,6-diaminopyridine to 2,6-bis(pivaloylamino)pyridine (6), directed lithiation with n-butyllithium, treatment with N-formylmorpholine, and hydrolysis produced 4 in 67% overall yield. The Friedlander condensation of 4 with a variety of activated and unactivated ketones afforded 2-amino-1,8-naphthyridines and bis(2-amino-1,8-naphthyridines) in moderate to good yields, providing a convenient synthesis of useful building blocks for new host-guest and self-assembling systems.

  DOI：

  10.1021/jo00076a021
• 作为产物：
  描述：

  2,6-二氨基吡啶 在 哌啶 、 氢氧化钾 、 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 80.0h， 生成 7-(Acetylamino)-3-carbethoxy-1,8-naphthyridin-(1H)2-one
  参考文献：
  名称：

  Convenient synthesis of 2-amino-1,8-naphthyridines, building blocks for host-guest and self-assembling systems

  摘要：

  Application of the Reimer-Tiemann reaction to 2,6-diaminopyridine afforded a 26% yield of 2,6-diaminopyridine-3-carboxaldehyde (4) and a small amount (4%) of 2,6-diaminopyridine-3,5-dicarboxaldehyde. Alternatively, conversion of 2,6-diaminopyridine to 2,6-bis(pivaloylamino)pyridine (6), directed lithiation with n-butyllithium, treatment with N-formylmorpholine, and hydrolysis produced 4 in 67% overall yield. The Friedlander condensation of 4 with a variety of activated and unactivated ketones afforded 2-amino-1,8-naphthyridines and bis(2-amino-1,8-naphthyridines) in moderate to good yields, providing a convenient synthesis of useful building blocks for new host-guest and self-assembling systems.

  DOI：

  10.1021/jo00076a021

文献信息

• 7-amido-1,8-naphthyridines as hydrogen bonding units for the complexation of guanine derivatives: The role of 2-alkoxyl groups in decreasing binding affinity
  作者：Thomas J. Murray、Steven C. Zimmerman

  DOI：10.1016/0040-4039(95)01586-7

  日期：1995.10

  The unusually low stability of a hydrogen bonded complex between a guanosine derivative and a 7-amido-2-alkoxy-1,8-naphthyridine, containing the DAA-ADD motif, can be explained by a conformational/steric effect.

  鸟嘌呤衍生物和含有DAA-ADD基序的7-氨基-2-烷氧基-1,8-萘啶之间的氢键复合物的异常低的稳定性可以通过构象/空间效应来解释。