1,6-dihydro-6-imino-1-methylpyrimidine | 52731-57-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1,6-dihydro-6-imino-1-methylpyrimidine
• 英文别名: 1,6-Dihydro-6-imino-1-methylpyrimidin；3-methyl-3H-pyrimidin-4-ylideneamine；3-Methylpyrimidin-4-imine
• CAS: 52731-57-4
• 化学式: C₅H₇N₃
• 分子量: 109.131
• InChiKey: XPQCWKVOHGIZNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  39.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,6-dihydro-6-imino-1-methylpyrimidine 在 氢氧化钾 作用下， 以 水 为溶剂， 以95%的产率得到4-甲氨基嘧啶
  参考文献：
  名称：

  Buurman, Dick J.; Plas, Henk C. van der, Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 1377 - 1380

  摘要：

  DOI：
• 作为产物：
  描述：

  1-methylpyrimidin-1-ium iodide 在 potassium permanganate 作用下， 以 氨 为溶剂， 反应 4.0h， 以85%的产率得到1,6-dihydro-6-imino-1-methylpyrimidine
  参考文献：
  名称：

  Buurman, Dick J.; Plas, Henk C. van der, Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 1377 - 1380

  摘要：

  DOI：

文献信息

• Amino–imino tautomerization reaction of the 4-aminopyrimidine/acetic acid system
  作者：Teruyoshi Kitamura、Masahiro Okita、Yutaka Sasaki、Hironori Ishikawa、Akira Fujimoto

  DOI：10.1016/j.saa.2007.04.006

  日期：2008.2

  The amino-imino tautomerization of the 4-aminopyrimidine (4APM)/acetic acid (AcOH) system through dual hydrogen bonding in n-hexane at room temperature was investigated using UV absorption and fluorescence spectroscopies, fluorescence time-profile measurements, and molecular orbital calculations, with those of the imino-model compound of 3-methyl-4(1H)-pyrimidinimine (3M4PMI). From the experimental results, it was confirmed that the imino-tautomer was formed in the first excited singlet state (S1) state through the double-proton transfer of the dual hydrogen-bonded complex of 4APM with AcOH. The fluorescences of the free 4APM monomer (band maximum at 353 nm), imino-tautomer (at 414 nm), and 3M4PMI monomer (at 437 nm) exhibit the single-exponential decays of 98, 73, and 19 ps time constants, respectively. The shorter decay time of the imino-tautomer fluorescence compared with the free monomer one is suggestive of the low activation energy process in the S1 state. From the result of the shortest decay time of the 3M4PMI fluorescence, it can be deduced that 3M4PMI has a non-planar structure in the S1 state. The theoretical calculations on the S0 and S1 state double-proton transfer for the 4APM/AcOH dual hydrogen-bonded system were performed with the use of formic acid (FoOH) in place of AcOH for the sake of simplicity. Only one peak of transition state was resolved in the S0 and S1 states. The energy barrier for the S1 state double-proton transfer of the 4APM/FoOH complex -> 3H-4(1H)-pyrimidinimine/FoOH tautomer was estimated to be similar to 2 kJ mol(-1) using the CIS/6-31G(d) methods. On the other hand, the energy barrier for the SO state reverse proton transfer of the 3H-4(1H)-pyrimidinimine/FoOH tautomer -> 4APM/FoOH complex was estimated to be almost zero kJ mol(-1) at B3LYP/6-31G(d) level. (C) 2007 Elsevier B.V. All rights reserved.
• Buurman, Dick J.; Plas, Henk C. van der, Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 1377 - 1380
  作者：Buurman, Dick J.、Plas, Henk C. van der

  DOI：——

  日期：——