8-<4-(trifluoromethyl)phenyl>-1,3-dimethylxanthine | 149981-16-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 8-<4-(trifluoromethyl)phenyl>-1,3-dimethylxanthine
• 英文别名: 1,3-Dimethyl-8-(4-trifluoromethyl-phenyl)-3,7-dihydro-purine-2,6-dione；1,3-dimethyl-8-[4-(trifluoromethyl)phenyl]-7H-purine-2,6-dione
• CAS: 149981-16-8
• 化学式: C₁₄H₁₁F₃N₄O₂
• 分子量: 324.262
• InChiKey: LJKTYIMVCCWFOK-UHFFFAOYSA-N

物化性质

• 沸点：
  502.3±60.0 °C(Predicted)
• 密度：
  1.462±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-<4-(trifluoromethyl)phenyl>-1,3-dimethylxanthine 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以92%的产率得到8-<4-(trifluoromethyl)phenyl>-1,3,7-trimethylxanthine
  参考文献：
  名称：

  Effect of trifluoromethyl and other substituents on activity of xanthines at adenosine receptors

  摘要：

  An aryl p-(trifluoromethyl) substituent increases the affinity of 1,3-disubstituted 8-phenylxanthines at A2a-adenosine receptors, while having little effect on affinity at Al-adenosine receptors. In contrast, an aryl p-(trifluoromethyl) substituent has little effect on affinity of 3,7-disubstituted and 1,3,7-trisubstituted 8-phenylxanthines. An aryl p-sulfo substituent reduces affinity of all 8-phenylxanthines at A1-and A2a-adenosine receptors. An 8-(trifluoromethyl) substituent markedly reduces affinity of 1,3-dialkylxanthines at both A1- and A2a-adenosine receptors. In contrast, 8-(trifluoromethyl)caffeine retains affinity for A2a-adenosine receptors, but does lose affinity for A1-adenosine receptors. 8-Bromo-, 8-acryl-, and 8-pent-1-enylcaffeines are also selective for A2-adenosine receptors, while 8-cyclobutylcaffeine is nonselective. 8-[trans-2-(tert-butyloxycarbonyl)vinylcaffeine is 20-fold selective for Aza vs A1 receptors.

  DOI：

  10.1021/jm00070a007
• 作为产物：
  描述：

  5,6-二氨基-1,3-二甲基脲嘧啶 在 吡啶 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 8-<4-(trifluoromethyl)phenyl>-1,3-dimethylxanthine
  参考文献：
  名称：

  Effect of trifluoromethyl and other substituents on activity of xanthines at adenosine receptors

  摘要：

  An aryl p-(trifluoromethyl) substituent increases the affinity of 1,3-disubstituted 8-phenylxanthines at A2a-adenosine receptors, while having little effect on affinity at Al-adenosine receptors. In contrast, an aryl p-(trifluoromethyl) substituent has little effect on affinity of 3,7-disubstituted and 1,3,7-trisubstituted 8-phenylxanthines. An aryl p-sulfo substituent reduces affinity of all 8-phenylxanthines at A1-and A2a-adenosine receptors. An 8-(trifluoromethyl) substituent markedly reduces affinity of 1,3-dialkylxanthines at both A1- and A2a-adenosine receptors. In contrast, 8-(trifluoromethyl)caffeine retains affinity for A2a-adenosine receptors, but does lose affinity for A1-adenosine receptors. 8-Bromo-, 8-acryl-, and 8-pent-1-enylcaffeines are also selective for A2-adenosine receptors, while 8-cyclobutylcaffeine is nonselective. 8-[trans-2-(tert-butyloxycarbonyl)vinylcaffeine is 20-fold selective for Aza vs A1 receptors.

  DOI：

  10.1021/jm00070a007

文献信息

• A facile and rapid one-step synthesis of 8-substituted xanthine derivatives via tandem ring closure at room temperature
  作者：Prabal Bandyopadhyay、Sumit K. Agrawal、Manisha Sathe、Pratibha Sharma、M.P. Kaushik

  DOI：10.1016/j.tet.2012.03.050

  日期：2012.5

  N-Bromo succinimide (NBS) was found to be an efficient and regioselective reagent in combination with AIBN for an unprecedented, facile and rapid one-step synthesis of 8-substituted xanthine derivatives at room temperature. The inexpensive, nontoxic and readily available NBS efficiently promoted the condensation of several aryl/cycloaryl/heteroaryl aldehydes with 5,6-diamino-1,3-dimethyluracils in

  N-溴代琥珀酰亚胺（NBS）与AIBN结合使用是一种高效且区域选择性的试剂，可在室温下空前，简便，快速地一步合成8-取代的黄嘌呤衍生物。在催化量的AIBN存在下，通过自由基链反应，在一步催化过程中，廉价，无毒且易于获得的NBS有效地促进了几种芳基/环芳基/杂芳基醛与5,6-二氨基-1,3-二甲基尿嘧啶的缩合。该方案的显着优点是反应时间短，反应条件温和，后处理简单，无需色谱分离，使用无害试剂/溶剂且适用于多种底物。