6-thiophen-2-yl-2H-[1,2,4]triazine-3,5-dione | 156270-70-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 6-thiophen-2-yl-2H-[1,2,4]triazine-3,5-dione
• 英文别名: 6-thiophen-2-yl-2H-1,2,4-triazine-3,5-dione
• CAS: 156270-70-1
• 化学式: C₇H₅N₃O₂S
• 分子量: 195.202
• InChiKey: DMLJWAKNASIKEM-UHFFFAOYSA-N

物化性质

• 密度：
  1.75±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-thiophen-2-yl-2H-[1,2,4]triazine-3,5-dione 在 六甲基二硅氮烷 作用下， 以 氯仿 为溶剂， 反应 16.0h， 生成 5-(2-thienyl)-1-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-6-azauracyl
  参考文献：
  名称：

  The Synthesis of Some 5-Substituted-6-aza-2′-deoxyuridines

  摘要：

  5-(2-Thienyl)-1-(2-deoxy-3,5-di-O-p-toluoyl-beta-D-erythro-pentofuranosyl)-6-azauracil [VIII] and 5-cyclopropyl-1-(2-deoxy-3,5-di-O-p-toluoyl-beta-D-erythro-pentofuranosyl)-6-azauracil [X] were obtained in high yields (93.5% and 81.3% respectively) exclusively as beta anomers, by condensation of the corresponding silylated triazine bases with 2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentosyl chloride in chloroform. After deblocking both nucleosides with sodium methoxide in methanol, 5-(2-thienyl)-6-aza-2'-deoxyuridine [IX] and 5-cyclopropyl-6-aza-2'-deoxyuridine [XI] were obtained. The nucleoside IX was further acetylated, brominated with Br-2/CCl4 and deblocked with methanolic ammonia to give 6-aza-5[2-(5-bromothienyl)]-2'-deoxyuridine [XIV].

  DOI：

  10.1080/15257779408013233
• 作为产物：
  描述：

  2-噻吩乙醛酸 在 sodium hydroxide 、 氯乙酸 作用下， 以 水 为溶剂， 反应 46.0h， 生成 6-thiophen-2-yl-2H-[1,2,4]triazine-3,5-dione
  参考文献：
  名称：

  The Synthesis of Some 5-Substituted-6-aza-2′-deoxyuridines

  摘要：

  5-(2-Thienyl)-1-(2-deoxy-3,5-di-O-p-toluoyl-beta-D-erythro-pentofuranosyl)-6-azauracil [VIII] and 5-cyclopropyl-1-(2-deoxy-3,5-di-O-p-toluoyl-beta-D-erythro-pentofuranosyl)-6-azauracil [X] were obtained in high yields (93.5% and 81.3% respectively) exclusively as beta anomers, by condensation of the corresponding silylated triazine bases with 2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentosyl chloride in chloroform. After deblocking both nucleosides with sodium methoxide in methanol, 5-(2-thienyl)-6-aza-2'-deoxyuridine [IX] and 5-cyclopropyl-6-aza-2'-deoxyuridine [XI] were obtained. The nucleoside IX was further acetylated, brominated with Br-2/CCl4 and deblocked with methanolic ammonia to give 6-aza-5[2-(5-bromothienyl)]-2'-deoxyuridine [XIV].

  DOI：

  10.1080/15257779408013233

文献信息

• Modified 6-Aza Uridines: Highly Emissive pH-Sensitive Fluorescent Nucleosides
  作者：Renatus W. Sinkeldam、Patrycja A. Hopkins、Yitzhak Tor

  DOI：10.1002/cphc.201200375

  日期：2012.10.8

  Optimized facile syntheses and highly desirable spectroscopic properties of two isomorphic fluorescent pyrimidines, comprising a 1,2,4‐triazine motif conjugated to a thiophene (1 a) or a furan (1 b), are described. Although structurally related to their 5‐modified uridine counterparts, these modified 6‐aza‐uridines reveal dramatically improved fluorescence properties and a remarkable sensitivity to

  描述了两种同构荧光嘧啶的优化简便合成和非常理想的光谱特性，包括与噻吩 ( 1a ) 或呋喃 ( 1b )共轭的 1,2,4-三嗪基序。尽管在结构上与其 5-修饰的尿苷对应物相关，但这些修饰的 6-氮杂-尿苷显示出显着改善的荧光特性以及对极性和 pH 变化的显着敏感性。噻吩衍生物1a在 335 nm 附近具有最大吸收，在激发时产生极性敏感的最大可见光发射和荧光量子产率范围从 415 nm ( Φ =0.8) 到 455 nm ( Φ =0.2) 在二恶烷和水中， 分别。核苷1a也表现出对酸度的敏感性。将发射强度和溶液 pH 值相关联得出 ap K a值为 6.7-6.9，相当接近生理 pH 值。结果表明，广受欢迎的荧光特征（亮度和响应性）不一定是单独的大荧光团的特征，但可以用满足严格同构设计标准的探针观察到。
• Basnak; Sun; Hamor, Nucleosides and Nucleotides, 1998, vol. 17, # 1-3, p. 187 - 206
  作者：Basnak、Sun、Hamor、Focher、Verri、Spadari、Wroblowski、Herdewijn、Walker

  DOI：——

  日期：——
• The Synthesis of Some 5-Substituted-6-aza-2′-deoxyuridines
  作者：I. Basnak、P. L. Coe、R. T. Walker

  DOI：10.1080/15257779408013233

  日期：1994.3

  5-(2-Thienyl)-1-(2-deoxy-3,5-di-O-p-toluoyl-beta-D-erythro-pentofuranosyl)-6-azauracil [VIII] and 5-cyclopropyl-1-(2-deoxy-3,5-di-O-p-toluoyl-beta-D-erythro-pentofuranosyl)-6-azauracil [X] were obtained in high yields (93.5% and 81.3% respectively) exclusively as beta anomers, by condensation of the corresponding silylated triazine bases with 2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentosyl chloride in chloroform. After deblocking both nucleosides with sodium methoxide in methanol, 5-(2-thienyl)-6-aza-2'-deoxyuridine [IX] and 5-cyclopropyl-6-aza-2'-deoxyuridine [XI] were obtained. The nucleoside IX was further acetylated, brominated with Br-2/CCl4 and deblocked with methanolic ammonia to give 6-aza-5[2-(5-bromothienyl)]-2'-deoxyuridine [XIV].