5-(4-氟苯基)-4-甲基-1-丙基咪唑-2-胺 | 918801-76-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-(4-氟苯基)-4-甲基-1-丙基咪唑-2-胺
• 英文名称: 5-(4-fluorophenyl)-4-methyl-1-propyl-1H-imidazol-2-ylamine
• 英文别名: 5-(4-Fluorophenyl)-4-methyl-1-propyl-1H-imidazol-2-amine；5-(4-fluorophenyl)-4-methyl-1-propylimidazol-2-amine
• CAS: 918801-76-0
• 化学式: C₁₃H₁₆FN₃
• 分子量: 233.289
• InChiKey: HYOXNIQEKPDQTG-UHFFFAOYSA-N

物化性质

• 熔点：
  139-141 °C
• 沸点：
  393.7±34.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 一水合肼 作用下， 以 乙腈 为溶剂， 反应 0.08h， 生成 5-(4-氟苯基)-4-甲基-1-丙基咪唑-2-胺
  参考文献：
  名称：

  A Divergent Synthesis of Substituted 2-Aminoimidazoles from 2-Aminopyrimidines

  摘要：

  A new divergent and efficient synthesis of substituted 2-aminoimidazoles 5 and 6 has been developed starting from the readily available 2-aminopyrimidines 1 and alpha-broinocarbonyl compounds 2, Using conventional heating or microwave irradiation. Thus, the cleavage of 1,2,3-substituted imidazo[1,2-a]pyrimidin-1 -iumsalts 4 with hydrazine or secondary amines led to 1,4,5-trisubstituted 2-aminoimidazoles 5, when the hydrazinolysis of 2-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium salts 3, followed by a novel Dimroth-type rearrangement, resulted in formation of 2-amino-1H-imidazoles 6. The relevant pathway of transformations was identified by characterization of the intermediates.

  DOI：

  10.1021/jo8008758

文献信息

• Efficient One-Pot, Two-Step, Microwave-Assisted Procedure for the Synthesis of Polysubstituted 2-Aminoimidazoles
  作者：Denis S. Ermolat'ev、Eugene V. Babaev、Erik V. Van der Eycken

  DOI：10.1021/ol062421c

  日期：2006.12.1

  A microwave-assisted, one-pot, two-step protocol was developed for the construction of polysubstituted 2-aminoimidazoles. This process involves the sequential formation of imidazo[1,2-a]pyrimidinium salts from readily available 2-aminopyrimidines and alpha-bromocarbonyl compounds, followed by opening of the pyrimidine ring with hydrazine. [reaction: see text]

  开发了微波辅助的一锅两步操作规程，用于构建多取代的2-氨基咪唑。该过程涉及由容易获得的2-氨基嘧啶和α-溴羰基化合物顺序形成咪唑并[1,2-a]嘧啶鎓盐，然后用肼打开嘧啶环。[反应：看文字]
• A Divergent Synthesis of Substituted 2-Aminoimidazoles from 2-Aminopyrimidines
  作者：Denis S. Ermolat’ev、Erik V. Van der Eycken

  DOI：10.1021/jo8008758

  日期：2008.9.1

  A new divergent and efficient synthesis of substituted 2-aminoimidazoles 5 and 6 has been developed starting from the readily available 2-aminopyrimidines 1 and alpha-broinocarbonyl compounds 2, Using conventional heating or microwave irradiation. Thus, the cleavage of 1,2,3-substituted imidazo[1,2-a]pyrimidin-1 -iumsalts 4 with hydrazine or secondary amines led to 1,4,5-trisubstituted 2-aminoimidazoles 5, when the hydrazinolysis of 2-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium salts 3, followed by a novel Dimroth-type rearrangement, resulted in formation of 2-amino-1H-imidazoles 6. The relevant pathway of transformations was identified by characterization of the intermediates.