5-amino-3-(cyanomethyl)-1-methyl-1H-pyrazole-4-carbonitrile | 53871-49-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-amino-3-(cyanomethyl)-1-methyl-1H-pyrazole-4-carbonitrile
• 英文别名: (5-Amino-4-cyano-1-methyl-pyrazolyl-(3))-acetonitril；(5-amino-4-cyano-1-methyl-1H-pyrazol-3-yl)-acetonitrile；(5-Amino-4-cyan-1-methyl-1H-pyrazol-3-yl)-acetonitril；5-amino-3-(cyanomethyl)-1-methylpyrazole-4-carbonitrile
• CAS: 53871-49-1
• 化学式: C₇H₇N₅
• mdl: MFCD00115982
• 分子量: 161.166
• InChiKey: AKNBVYKHUHEZDT-UHFFFAOYSA-N

物化性质

• 熔点：
  178-179 °C(Solv: water (7732-18-5))
• 沸点：
  428.4±45.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  91.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-amino-3-(cyanomethyl)-1-methyl-1H-pyrazole-4-carbonitrile 在 sodium hydroxide 、 水 作用下， 生成 5-氨基-1,3-二甲基吡唑
  参考文献：
  名称：

  The Reaction of Malononitrile with Hydrazine^1,2

  摘要：

  DOI：

  10.1021/ja01519a044
• 作为产物：
  描述：

  2-氨基-1-丙烯基-1,1,3-三甲腈 、 甲基肼 以 乙醇 为溶剂， 反应 0.75h， 以53%的产率得到5-amino-3-(cyanomethyl)-1-methyl-1H-pyrazole-4-carbonitrile
  参考文献：
  名称：

  Divergent cyclisations of 2-(5-amino-4-carbamoyl-1H-pyrazol-3-yl)acetic acids with formyl and acetyl electrophiles

  摘要：

  The reaction of 2-(5-amino-4-carbamoyl-1-methyl-1H-pyrazol-3-yl) acetic acid and triethylorthoformate did not give the expected dihydropyrazolo[4,3-c]pyridin-4-one product as described in literature, but formed an alternative cyclic imide product, fully characterised by NMR and X-ray crystallography. This mode of reaction was shown to be general to other 1-substituted-2-(5-amino-4-carbamoyl-1H- pyrazol-3-yl) acetic acids. The outcome of the cyclisation was highly sensitive both to the nature of the reagents used and also to the acidity of the reaction medium, such that a number of interesting bicyclic heterocycles could be produced in a controlled fashion from the single starting material. The major tautomeric forms of the bicyclic products in solution were found to vary according to their substitution pattern. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.034

文献信息

• HETEROCYCLIC COMPOUNDS
  申请人：Ajinomoto Co., Inc.

  公开号：EP1396493A1

  公开（公告）日：2004-03-10

  A pharmaceutical composition containing a heterocyclic compound of the formula (I) wherein each symbol is as defined in the specification, an isomer thereof, a solvate thereof or a pharmaceutically acceptable salt thereof as an active ingredient has a superior TNF-α production suppressing action. Accordingly, it is useful for the prophylaxis or treatment of various diseases caused by abnormal production of TNF-α.

  一种含有式(I)杂环化合物的药物组合物 其中各符号如说明书中所定义）的杂环化合物、其异构体、其溶液或其药学上可接受的盐作为活性成分的药物组合物，具有优异的抑制 TNF-α 生成的作用。因此，它可用于预防或治疗由 TNF-α 的异常产生引起的各种疾病。
• Heterocyclic compounds
  申请人：——

  公开号：US20040147546A1

  公开（公告）日：2004-07-29

  A pharmaceutical composition containing a heterocyclic compound of the formula (I) 1 wherein each symbol is as defined in the specification, an isomer thereof, a solvate thereof or a pharmaceutically acceptable salt thereof as an active ingredient has a superior TNF-&agr; production suppressing action. Accordingly, it is useful for the prophylaxis or treatment of various diseases caused by abnormal production of TNF-&agr;.

  一种含有式 (I) 杂环化合物的药物组合物 1 其中各符号如说明书中所定义）的杂环化合物、其异构体、其溶液或其药学上可接受的盐作为活性成分的药物组合物，具有优异的 TNF-&agr; 生成抑制作用。因此，它可用于预防或治疗由 TNF-&agr; 异常产生引起的各种疾病。
• US7902179B2
  申请人：——

  公开号：US7902179B2

  公开（公告）日：2011-03-08
• The Reaction of Malononitrile with Hydrazine^1,2
  作者：Edward C. Taylor、Klaus S. Hartke

  DOI：10.1021/ja01519a044

  日期：1959.5
• Divergent cyclisations of 2-(5-amino-4-carbamoyl-1H-pyrazol-3-yl)acetic acids with formyl and acetyl electrophiles
  作者：Lynette A. Smyth、Thomas P. Matthews、Peter N. Horton、Michael. B. Hursthouse、Ian Collins

  DOI：10.1016/j.tet.2007.07.034

  日期：2007.9

  The reaction of 2-(5-amino-4-carbamoyl-1-methyl-1H-pyrazol-3-yl) acetic acid and triethylorthoformate did not give the expected dihydropyrazolo[4,3-c]pyridin-4-one product as described in literature, but formed an alternative cyclic imide product, fully characterised by NMR and X-ray crystallography. This mode of reaction was shown to be general to other 1-substituted-2-(5-amino-4-carbamoyl-1H- pyrazol-3-yl) acetic acids. The outcome of the cyclisation was highly sensitive both to the nature of the reagents used and also to the acidity of the reaction medium, such that a number of interesting bicyclic heterocycles could be produced in a controlled fashion from the single starting material. The major tautomeric forms of the bicyclic products in solution were found to vary according to their substitution pattern. (c) 2007 Elsevier Ltd. All rights reserved.