2-(4-氯苯胺基)-1H-嘧啶-6-酮 | 158661-61-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(4-氯苯胺基)-1H-嘧啶-6-酮
• 英文名称: 2-(4-chlorophenylamino)-1H-pyrimidine-4-one
• 英文别名: 2-(4-chloroanilino)-1H-pyrimidin-6-one
• CAS: 158661-61-1
• 化学式: C₁₀H₈ClN₃O
• 分子量: 221.646
• InChiKey: MEUBCTJJRTXLLI-UHFFFAOYSA-N

物化性质

• 熔点：
  242-244 °C
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-氯苯胺基)-1H-嘧啶-6-酮 在 ammonium sulfate 、 氨 、 六甲基二硅氮烷 作用下， 以 甲醇 为溶剂， 生成 1-(β-D-ribofuranosyl)-2-(4-chlorophenylamino)-1H-pyrimidin-4-one
  参考文献：
  名称：

  Synthesis of N 2-Arylisocytidines and N 2-Aryl-2′-deoxyisocytidines

  摘要：

  2-(Arylamino)pyrimidin-4-ones were synthesized, silylated, and condensed with l,2,3,5-tetra-O-acetyl-beta-D-ribofuranoside to afford the corresponding N-2-aryl protected isocytidines. Deprotection of the acetylated isocytidines using saturated NH3 in MeOH solution gave 1-(beta-D-ribofuranosyl)-2-(arylamino)-4-pyrimidinones. Methyl 2-deoxy-3,5-di-O-toluyl-alpha/beta-D-ribofuranoside was prepared and condensed with the previously silylated bases to afford the anomeric mixture of protected nucleosides. The pure beta-anomers were synthesized with better yield by treating the sodium salts of N-2-arylisocytosine derivatives with 2-deoxy-3,5-di-O-toluyl-alpha-D-ribofuranosyl chloride. Deprotection of the latter anomers afforded the corresponding free hydroxyl derivatives. The synthesized free nucleosides are under antiviral and oligonucleotide investigations.

  DOI：

  10.1007/s00706-007-0671-9
• 作为产物：
  描述：

  2-甲硫基-4-嘧啶酮 、 对氯苯胺 在 三甲基乙酸 作用下， 生成 2-(4-氯苯胺基)-1H-嘧啶-6-酮
  参考文献：
  名称：

  SNAr Reactions of 2-Methylthio-4-pyrimidinones in Pivalic Acid: Access to Functionalized Pyrimidinones and Pyrimidines

  摘要：

  皮伐酸是一种有效的介质，可以直接实现2-甲硫基-4-吡啶酮与多种芳香胺的SNAr置换反应。产物易于分离，收益良好至优秀，随后进行氯化，可以为快速探究功能化吡啶的4位结构-活性关系提供机会。

  DOI：

  10.1055/s-0031-1289744

文献信息

• 71. Synthetic antimalarials. Part IV. 2-Phenylguanidino-4-aminoalkylamino-6-methylpyrimidines
  作者：F. H. S. Curd、F. L. Rose

  DOI：10.1039/jr9460000362

  日期：——
• A Facile Preparation of N²-Arylisocytosines
  作者：Jarosław Spychała

  DOI：10.1080/00397919708006796

  日期：1997.6

  N-2-Arylisocytosines were obtained in good yields varying from 59 to 96% by a simple two-step process starting from 2-thiouracil via readily accessible 2-(methylthio)pyrimidin-4(3H)-one.
• SNAr Reactions of 2-Methylthio-4-pyrimidinones in Pivalic Acid: Access to Functionalized Pyrimidinones and Pyrimidines
  作者：Matthew Maddess、Rhiannon Carter

  DOI：10.1055/s-0031-1289744

  日期：2012.4

  Pivalic acid is a useful medium to effect the direct SNAr displacement of 2-methylthio-4-pyrimidinones with a variety of anilines. Products are easily isolated in good to excellent yields, and following chlorination, provide an opportunity to rapidly query structure-activity relationships at the 4-position of functionalized pyrimidines.

  皮伐酸是一种有效的介质，可以直接实现2-甲硫基-4-吡啶酮与多种芳香胺的SNAr置换反应。产物易于分离，收益良好至优秀，随后进行氯化，可以为快速探究功能化吡啶的4位结构-活性关系提供机会。
• Synthesis of N 2-Arylisocytidines and N 2-Aryl-2′-deoxyisocytidines
  作者：Omar M. Ali

  DOI：10.1007/s00706-007-0671-9

  日期：2007.9

  2-(Arylamino)pyrimidin-4-ones were synthesized, silylated, and condensed with l,2,3,5-tetra-O-acetyl-beta-D-ribofuranoside to afford the corresponding N-2-aryl protected isocytidines. Deprotection of the acetylated isocytidines using saturated NH3 in MeOH solution gave 1-(beta-D-ribofuranosyl)-2-(arylamino)-4-pyrimidinones. Methyl 2-deoxy-3,5-di-O-toluyl-alpha/beta-D-ribofuranoside was prepared and condensed with the previously silylated bases to afford the anomeric mixture of protected nucleosides. The pure beta-anomers were synthesized with better yield by treating the sodium salts of N-2-arylisocytosine derivatives with 2-deoxy-3,5-di-O-toluyl-alpha-D-ribofuranosyl chloride. Deprotection of the latter anomers afforded the corresponding free hydroxyl derivatives. The synthesized free nucleosides are under antiviral and oligonucleotide investigations.