5-(tert-butyldithiomethyl)uracil | 180714-52-7

• 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: 5-(tert-butyldithiomethyl)uracil
• 英文别名: 5-[(tert-butyldisulfanyl)methyl]-1H-pyrimidine-2,4-dione
• CAS: 180714-52-7
• 化学式: C₉H₁₄N₂O₂S₂
• 分子量: 246.354
• InChiKey: IKVMZOWASZPZAG-UHFFFAOYSA-N

物化性质

• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(tert-butyldithiomethyl)uracil 在 sodium hydroxide 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 N-[2-(N-9-fluorenylmethoxycarbonyl)aminoethyl]-N-[5-(tert-butyldithiomethyl)uracil-1-ylmethylcarbonyl]glycine
  参考文献：
  名称：

  Improved Nucleic Acid Triggered Probe Activation through the Use of a 5-Thiomethyluracil Peptide Nucleic Acid Building Block

  摘要：

  To improve the efficiency of a nucleic acid triggered probe activation (NATPA) system a 5-thiomethyluracil peptide nucleic acid (PNA) building block has been synthesized. Attachment of imidazole and a coumarin ester to uracils at the ends of two PNAs resulted in a 550 000-fold acceleration of DNA-triggered coumarin release relative to imidazole and a 6-fold increase in k(cat) relative to a system which had these groups attached to the amino and carboxy ends of PNAs.

  DOI：

  10.1021/ol0478382
• 作为产物：
  描述：

  5-(氯甲基)尿嘧啶 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 5-(tert-butyldithiomethyl)uracil
  参考文献：
  名称：

  Improved Nucleic Acid Triggered Probe Activation through the Use of a 5-Thiomethyluracil Peptide Nucleic Acid Building Block

  摘要：

  To improve the efficiency of a nucleic acid triggered probe activation (NATPA) system a 5-thiomethyluracil peptide nucleic acid (PNA) building block has been synthesized. Attachment of imidazole and a coumarin ester to uracils at the ends of two PNAs resulted in a 550 000-fold acceleration of DNA-triggered coumarin release relative to imidazole and a 6-fold increase in k(cat) relative to a system which had these groups attached to the amino and carboxy ends of PNAs.

  DOI：

  10.1021/ol0478382

文献信息

• Efficient Synthesis of 5-(Thioalkyl)uridines <i>via</i> Ring Opening of α-Ureidomethylene Thiolactones
  作者：Sengen Sun、Xiao-Qing Tang、Aziz Merchant、P. S. R. Anjaneyulu, and、Joseph A. Piccirilli*

  DOI：10.1021/jo960966m

  日期：1996.1.1
• Improved Nucleic Acid Triggered Probe Activation through the Use of a 5-Thiomethyluracil Peptide Nucleic Acid Building Block
  作者：Jianfeng Cai、Xiaoxu Li、John Stephen Taylor

  DOI：10.1021/ol0478382

  日期：2005.3.1

  To improve the efficiency of a nucleic acid triggered probe activation (NATPA) system a 5-thiomethyluracil peptide nucleic acid (PNA) building block has been synthesized. Attachment of imidazole and a coumarin ester to uracils at the ends of two PNAs resulted in a 550 000-fold acceleration of DNA-triggered coumarin release relative to imidazole and a 6-fold increase in k(cat) relative to a system which had these groups attached to the amino and carboxy ends of PNAs.