4-(allylthio)-1-phenylpyrimidin-2(1H)-one | 917081-61-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(allylthio)-1-phenylpyrimidin-2(1H)-one
• 英文别名: 1-Phenyl-4-(2-propen-1-ylthio)-2(1H)-pyrimidinone；1-phenyl-4-prop-2-enylsulfanylpyrimidin-2-one
• CAS: 917081-61-9
• 化学式: C₁₃H₁₂N₂OS
• 分子量: 244.317
• InChiKey: RRNWJIKAIQDTQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  58
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-allylthiopyrimidin-2(1H)-one 、 苯硼酸 在 copper diacetate 吡啶 、 air 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以78%的产率得到4-(allylthio)-1-phenylpyrimidin-2(1H)-one
  参考文献：
  名称：

  Efficient N-Arylation and N-Alkenylation of the Five DNA/RNA Nucleobases

  摘要：

  [GRAPHICS]A general approach to N-arylation and N-alkenylation of all five DNA/RNA nucleobases at the nitrogen atom normally attached to the sugar moiety in DNA or RNA has been developed. Various protected or masked nucleobases engaged readily in the copper-mediated Chan-Lam-Evans-modified Ullmann condensation with a range of different boronic acids at room temperature and were subsequently converted to the corresponding deprotected or unmasked adducts. Different N-3-protecting groups were examined in the case of thymine, where the benzoyl group afforded the highest yields. A 4-alkylthio-substituted pyrimidin-2(1H)-one served as both a cytosine and a uracil precursor and was N-arylated and N-alkenylated in high yields. Adenine was efficiently and selectively N-arylated and N-alkenylated at the N-9 position by employing a bis-Boc-protected adenine derivative, while a bis-Boc-protected 2-amino-6-chloropurine served as guanine precursor and could also be selectively N-9-arylated and N-9-alkenylated.

  DOI：

  10.1021/jo061694i

文献信息

• Efficient <i>N</i>-Arylation and <i>N</i>-Alkenylation of the Five DNA/RNA Nucleobases
  作者：Mikkel F. Jacobsen、Martin M. Knudsen、Kurt V. Gothelf

  DOI：10.1021/jo061694i

  日期：2006.11.1

  [GRAPHICS]A general approach to N-arylation and N-alkenylation of all five DNA/RNA nucleobases at the nitrogen atom normally attached to the sugar moiety in DNA or RNA has been developed. Various protected or masked nucleobases engaged readily in the copper-mediated Chan-Lam-Evans-modified Ullmann condensation with a range of different boronic acids at room temperature and were subsequently converted to the corresponding deprotected or unmasked adducts. Different N-3-protecting groups were examined in the case of thymine, where the benzoyl group afforded the highest yields. A 4-alkylthio-substituted pyrimidin-2(1H)-one served as both a cytosine and a uracil precursor and was N-arylated and N-alkenylated in high yields. Adenine was efficiently and selectively N-arylated and N-alkenylated at the N-9 position by employing a bis-Boc-protected adenine derivative, while a bis-Boc-protected 2-amino-6-chloropurine served as guanine precursor and could also be selectively N-9-arylated and N-9-alkenylated.