1,2-dimethyl-8,9-dimethoxy-3H,5H-dipyrrolo[1,2-c:2',1'-f]pyrimidine-3,5-dione | 1186082-89-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并三嗪类
• 英文名称: 1,2-dimethyl-8,9-dimethoxy-3H,5H-dipyrrolo[1,2-c:2',1'-f]pyrimidine-3,5-dione
• CAS: 1186082-89-2
• 化学式: C₁₄H₁₄N₂O₄
• 分子量: 274.276
• InChiKey: BYIKCIIJBKWSRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.94
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  7,8-dimethoxy-2,3-dimethyl-10H-dipyrrin-1-one 、 N,N'-羰基二咪唑 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以91%的产率得到1,2-dimethyl-8,9-dimethoxy-3H,5H-dipyrrolo[1,2-c:2',1'-f]pyrimidine-3,5-dione
  参考文献：
  名称：

  Methoxyl-induced fluorescence quenching in N,N′-bridged 9H-dipyrrinones and an X-ray crystal structure

  摘要：

  Strongly fluorescent dipyrrinones can be prepared by bridging the pyrrole and lactam nitrogens with a carbonyl group, from reaction with N,N'-carbonyldiimidazole in the presence of a strong, non-nucleophilic base. The yellow, N,N'-carbonyl-bridged dipyrrinones typically have fluorescent quantum yields (phi(F)) approaching 1.0. Thus, in chloroform, N,N'-bridged 9H-dipyrrinones with beta-alkyl substituents: 2,3-diethyl-7,8-dimethyl has phi(F) = 0.90 (lambda(em) = 465 nm) and 2,3-dimethyl-7,8-dimethoxy has phi(F) = 0.84 (lambda(em) = 482 nm). In contrast, 2,3-dimethoxy-7,8-dimethyl and 2,3,7,8-tetramethoxy show red-shifted lambda(em) but with strongly reduced phi(F): phi(F) = 0.10 (lambda(em) = 511 nm) and 0.08 (lambda(em) = 511 nm), respectively. Methoxy substituents on the lactam, but not the pyrrole ring act to quench the fluorescence and shift the emission and excitation wavelengths bathochromically. The first X-ray crystal structure of an N,N'-carbonyl-bridged dipyrrinone was obtained from 7,8-dimethoxy-2,3-dimethyl-10H-dipyrrin-1-one.

  DOI：

  10.1007/s00706-008-0924-2