羟基(5-嘧啶基)乙腈 | 287472-24-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 羟基(5-嘧啶基)乙腈
• 英文名称: hydroxy(pyrimidin-5-yl)acetonitrile
• 英文别名: 2-Hydroxy-2-(pyrimidin-5-YL)acetonitrile；2-hydroxy-2-pyrimidin-5-ylacetonitrile
• CAS: 287472-24-6
• 化学式: C₆H₅N₃O
• 分子量: 135.125
• InChiKey: VPBOBWNUNZTGPY-UHFFFAOYSA-N

物化性质

• 沸点：
  344.9±27.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  69.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  羟基(5-嘧啶基)乙腈 在 二氯化二硫 、 ammonium hydroxide 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.0h， 生成 3-氯-4-嘧啶-5-基-1,2,5-噻二唑
  参考文献：
  名称：

  Synthesis of 5-(4-Alkoxy-[1,2,5]thiadiazol-3-yl)-3-methyl-1,2,3,4- tetrahydropyrimidine Oxalate Salts and Their Evaluation as Muscarinic Receptor Agonists

  摘要：

  The synthesis and biological testing of 5-(4-alkoxy-[1,2,5]thiadiazol-3-yl)-3-methyl-1,2,3,4-tetrahydropyrimidine oxalate salts 8 as muscarinic receptor agonists are described. The key intermediate 4 was obtained by modified Strecker reaction and cyclization of starting material 1. Subsequent alkoxy substitution, quaternization and reduction afforded 7. For the sake of purity and stability of the final products 8, the 3-methyl-1,2,3,4-tetrahydropyrimidines were obtained as oxalic acid salts. All final compounds were examined in vitro for their binding affinities to the cloned human muscarinic receptor by the [H-3]-NMS binding assay.

  DOI：

  10.1002/(sici)1521-4184(20005)333:5<113::aid-ardp113>3.0.co;2-9
• 作为产物：
  描述：

  氰化钾 、 嘧啶-5-甲醛 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 以67%的产率得到羟基(5-嘧啶基)乙腈
  参考文献：
  名称：

  5-(4-烷基硫烷基-[1,2,5]噻二唑-3-基)-3-甲基-1,2,3,4-四氢嘧啶草酸盐的合成及其作为毒蕈碱受体激动剂的评价

  摘要：

  描述了作为毒蕈碱受体激动剂的5-(4-烷基硫基-[1,2,5]噻二唑-3-基)-3-甲基-1,2,3,4-四氢嘧啶草酸盐7的合成和生物学试验。关键中间体4通过改进的Strecker反应和环化得到，3-甲基-1,2,3,4-四氢嘧啶通过后续的取代、季铵化和还原得到。最终产物7以草酸盐形式获得。通过[3H]-NMS结合测定在体外检查制备的化合物对克隆的人毒蕈碱受体的结合亲和力。

  DOI：

  10.1002/ardp.200300730

文献信息

• Synthesis of 5-(4-Alkoxy-[1,2,5]thiadiazol-3-yl)-3-methyl-1,2,3,4- tetrahydropyrimidine Oxalate Salts and Their Evaluation as Muscarinic Receptor Agonists
  作者：Jewn-Giew Park、Mi-Jeoung Lee、Jae Yang Kong、Myung Hee Jung

  DOI：10.1002/(sici)1521-4184(20005)333:5<113::aid-ardp113>3.0.co;2-9

  日期：2000.5

  The synthesis and biological testing of 5-(4-alkoxy-[1,2,5]thiadiazol-3-yl)-3-methyl-1,2,3,4-tetrahydropyrimidine oxalate salts 8 as muscarinic receptor agonists are described. The key intermediate 4 was obtained by modified Strecker reaction and cyclization of starting material 1. Subsequent alkoxy substitution, quaternization and reduction afforded 7. For the sake of purity and stability of the final products 8, the 3-methyl-1,2,3,4-tetrahydropyrimidines were obtained as oxalic acid salts. All final compounds were examined in vitro for their binding affinities to the cloned human muscarinic receptor by the [H-3]-NMS binding assay.
• Synthesis of 5-(4-Alkylsulfanyl-[1, 2, 5]Thiadiazol-3-yl)-3-Methyl-1, 2, 3, 4-Tetrahydropyrimidine Oxalate Salts and their Evaluation as Muscarinic Receptor Agonists
  作者：Myung Hee Jung、Jewn-Giew Park、Woo-Kyu Park

  DOI：10.1002/ardp.200300730

  日期：2003.7

  The synthesis and biological test of 5‐(4‐alkylsulfanyl‐[1, 2, 5]thiadiazol‐3‐yl)‐3‐me‐thyl‐1, 2, 3, 4‐tetrahydropyrimidine oxalate salts 7 as muscarinic receptor agonists are described. The key intermediate 4 was obtained by a modified Strecker reaction and cyclization, and the 3‐methyl‐1, 2, 3, 4‐tetrahydropyrimidines were obtained by subsequent substitution, quarternization, and reduction. The final

  描述了作为毒蕈碱受体激动剂的5-(4-烷基硫基-[1,2,5]噻二唑-3-基)-3-甲基-1,2,3,4-四氢嘧啶草酸盐7的合成和生物学试验。关键中间体4通过改进的Strecker反应和环化得到，3-甲基-1,2,3,4-四氢嘧啶通过后续的取代、季铵化和还原得到。最终产物7以草酸盐形式获得。通过[3H]-NMS结合测定在体外检查制备的化合物对克隆的人毒蕈碱受体的结合亲和力。