2,6-二氨基-4-羟基吡啶(6ci,9ci) | 99845-76-8

• 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
• 中文名称: 2,6-二氨基-4-羟基吡啶(6ci,9ci)
• 英文名称: 4-hydroxy-pyridine-2,6-diamine
• 英文别名: 2,6-Diamino-4-hydroxy-pyridin；4-hydroxy-2,6-diaminopyridine；2,6-diamino-pyridin-4-ol；2,6-Diaminopyridin-4-ol；2,6-diamino-1H-pyridin-4-one
• CAS: 99845-76-8
• 化学式: C₅H₇N₃O
• mdl: MFCD13178783
• 分子量: 125.13
• InChiKey: DAHRVHXMNYUJFB-UHFFFAOYSA-N

物化性质

• 熔点：
  191 °C (decomp)
• 沸点：
  604.4±50.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.1
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  2,6-二氨基-4-羟基吡啶(6ci,9ci) 在 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 N-(6-乙酰氨基-4-氧代-1H-吡啶-2-基)乙酰胺
  参考文献：
  名称：

  A new versatile synthesis of 4-substituted diaminopyridine derivatives

  摘要：

  A new convenient method for the synthesis of substituted 2,6-diacetamido pyridines has been developed. It starts from 4-hydroxypyridine and comprises the introduction of the amino groups by the Chichibabin reaction. After several protection and deprotection steps 2,6-diacetamido-4-hydroxy pyridine is obtained, which is regarded as a key compound for the synthesis of various substituted 2,6-diacetamido pyridines. It is shown that the free hydroxy group is susceptible for nucleophilic substitution. This provides an easy access to the introduction of different functional groups at 4-position of 2,6-diacetamido pyridine. The advantages over other procedures described in the literature are discussed. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.089
• 作为产物：
  描述：

  4-羟基吡啶 在 碳酸氢钠 、 sodium amide 作用下， 以 水 、 paraffin 为溶剂， 反应 12.0h， 生成 2,6-二氨基-4-羟基吡啶(6ci,9ci)
  参考文献：
  名称：

  A new versatile synthesis of 4-substituted diaminopyridine derivatives

  摘要：

  A new convenient method for the synthesis of substituted 2,6-diacetamido pyridines has been developed. It starts from 4-hydroxypyridine and comprises the introduction of the amino groups by the Chichibabin reaction. After several protection and deprotection steps 2,6-diacetamido-4-hydroxy pyridine is obtained, which is regarded as a key compound for the synthesis of various substituted 2,6-diacetamido pyridines. It is shown that the free hydroxy group is susceptible for nucleophilic substitution. This provides an easy access to the introduction of different functional groups at 4-position of 2,6-diacetamido pyridine. The advantages over other procedures described in the literature are discussed. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.089

文献信息

• 2,6-Diamination of substituted pyridines via heterogeneous Chichibabin reaction
  作者：Matthias Mastalir、Ernst Pittenauer、Günter Allmaier、Karl Kirchner

  DOI：10.1016/j.tetlet.2015.12.013

  日期：2016.1

  initiated heterogeneous Chichibabin amination to obtain 2,6-diaminopyridine derivatives which are important synthons for the preparation of PNP pincer ligands. The substrates were treated with an excess of sodium amide in neat mineral oil as solvent under an argon atmosphere. The reaction required temperatures of up to 215 °C under vigorous stirring with an overall reaction time of 3–5 h. In the case

  选择一系列环取代的吡啶用于酰胺钠引发的异质壳多糖的胺化反应，以获得2，6-二氨基吡啶衍生物，其对于制备PNP钳位配体是重要的合成子。在氩气气氛下，在纯净的矿物油中用过量的酰胺钠作为溶剂处理基底。在剧烈搅拌下，该反应需要的温度高达215°C，总反应时间为3-5小时。在甲基，叔丁基，苯基，吡啶基和羟基取代的吡啶的情况下，所需产物以良好或优异的收率（63–96％）获得。因此，Chichibabin反应提供了一种从卤代吡啶或吡啶N开始的方法的廉价且经济的替代方法-氧化物，条件是取代基在苛刻的反应条件下是惰性的。
• Bojarska-Dahlig; Nantka-Namirski, Roczniki Chemii, 1956, vol. 30, p. 461,463
  作者：Bojarska-Dahlig、Nantka-Namirski

  DOI：——

  日期：——
• A new versatile synthesis of 4-substituted diaminopyridine derivatives
  作者：Sumela Banerjee、Brigitte Voit、Gert Heinrich、Frank Böhme

  DOI：10.1016/j.tetlet.2012.02.089

  日期：2012.4

  A new convenient method for the synthesis of substituted 2,6-diacetamido pyridines has been developed. It starts from 4-hydroxypyridine and comprises the introduction of the amino groups by the Chichibabin reaction. After several protection and deprotection steps 2,6-diacetamido-4-hydroxy pyridine is obtained, which is regarded as a key compound for the synthesis of various substituted 2,6-diacetamido pyridines. It is shown that the free hydroxy group is susceptible for nucleophilic substitution. This provides an easy access to the introduction of different functional groups at 4-position of 2,6-diacetamido pyridine. The advantages over other procedures described in the literature are discussed. (c) 2012 Elsevier Ltd. All rights reserved.