1,1'-Trimethylenebis(4-thiouracil) | 62242-34-6

• 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: 1,1'-Trimethylenebis(4-thiouracil)
• 英文别名: 1,1'-Trimethylenbis-4-thiouracil；1-[3-(2-Oxo-4-sulfanylidenepyrimidin-1-yl)propyl]-4-sulfanylidenepyrimidin-2-one
• CAS: 62242-34-6
• 化学式: C₁₁H₁₂N₄O₂S₂
• 分子量: 296.374
• InChiKey: VDUQIGRQHJKPCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1'-Trimethylenebis(4-thiouracil) 以 乙醇 、 丙酮 为溶剂， 反应 13.0h， 生成 1,1'-Trimethylenebis(N4-dimethylcytosine) photodimer
  参考文献：
  名称：

  Synthesis and Photochemical Cleavage of Cis-Syn Pyrimidine Cyclobutane Dimer Analogs

  摘要：

  The synthesis of cis-syn cytosine-cytosine and cytosine-thymine cyclobutane dimer analogs are described. In contrast to the thymine and uracil cyclobutane dimers, the cytosine-containing dimers have significant absorption bands in the UV-B region of the spectrum. These dimers can be reverted back to their monomeric form (split) by irradiation with UV Light. Additionally, the dimers can be split by photochemical electron transfer. Use of excited state electron donors N,N-dimethylaniline and N,N,N,N-tetramethylbenzidine gives high yields of the monomeric pyrimidines-even at high conversions. Use of excited-state electron accepters, 2-anthraquinonesulfonate and 9,10-dicyanoanthracene also resulted in efficient splitting. However the conversion-corrected chemical yields for these splitting reactions is much lower, due to the formation of a large number of side products.

  DOI：

  10.1021/jo00108a026

文献信息

• Synthesis and Photochemical Cleavage of Cis-Syn Pyrimidine Cyclobutane Dimer Analogs
  作者：David J. Fenick、Heather S. Carr、Daniel E. Falvey

  DOI：10.1021/jo00108a026

  日期：1995.2

  The synthesis of cis-syn cytosine-cytosine and cytosine-thymine cyclobutane dimer analogs are described. In contrast to the thymine and uracil cyclobutane dimers, the cytosine-containing dimers have significant absorption bands in the UV-B region of the spectrum. These dimers can be reverted back to their monomeric form (split) by irradiation with UV Light. Additionally, the dimers can be split by photochemical electron transfer. Use of excited state electron donors N,N-dimethylaniline and N,N,N,N-tetramethylbenzidine gives high yields of the monomeric pyrimidines-even at high conversions. Use of excited-state electron accepters, 2-anthraquinonesulfonate and 9,10-dicyanoanthracene also resulted in efficient splitting. However the conversion-corrected chemical yields for these splitting reactions is much lower, due to the formation of a large number of side products.