1-(2-deoxy-β-D-ribofuranosyl)-2-hydrazinopyrimidin-4-one | 1268475-33-7

• 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: 1-(2-deoxy-β-D-ribofuranosyl)-2-hydrazinopyrimidin-4-one
• 英文别名: 2-hydrazinyl-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-4-one
• CAS: 1268475-33-7
• 化学式: C₉H₁₄N₄O₄
• 分子量: 242.235
• InChiKey: DMHJEWBYCFRBBW-SHYZEUOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  120
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-deoxy-β-D-ribofuranosyl)-2-hydrazinopyrimidin-4-one 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.25h， 以40 mg的产率得到1-(2-deoxy-β-D-ribofuranosyl)tetrazolo[5,1-b]pyrimidin-4-one
  参考文献：
  名称：

  Synthesis and Photochemical Behavior of the Tetrazolo Tautomer of 2-Azido-4-pyrimidinone-2′-deoxyriboside

  摘要：

  The 2-azido analogue of 2'-deoxyuridine was prepared in three steps from 2'-deoxy-2-thiouridine. The sulfur atom of the 2-thio nucleoside was methylated and then displaced by hydrazine to furnish the corresponding 2-hydrazino derivative. After diazotization, the 2-azido compound that exists as its tetrazolo tautomer was obtained. Upon UV irradiation in aqueous solution, the title compound led to isocytosine.

  DOI：

  10.1021/jo102316r
• 作为产物：
  描述：

  2-硫代2'-脱氧尿苷 在 potassium carbonate 、 一水合肼 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 12.33h， 生成 1-(2-deoxy-β-D-ribofuranosyl)-2-hydrazinopyrimidin-4-one
  参考文献：
  名称：

  Synthesis and Photochemical Behavior of the Tetrazolo Tautomer of 2-Azido-4-pyrimidinone-2′-deoxyriboside

  摘要：

  The 2-azido analogue of 2'-deoxyuridine was prepared in three steps from 2'-deoxy-2-thiouridine. The sulfur atom of the 2-thio nucleoside was methylated and then displaced by hydrazine to furnish the corresponding 2-hydrazino derivative. After diazotization, the 2-azido compound that exists as its tetrazolo tautomer was obtained. Upon UV irradiation in aqueous solution, the title compound led to isocytosine.

  DOI：

  10.1021/jo102316r

文献信息

• Synthesis and Photochemical Behavior of the Tetrazolo Tautomer of 2-Azido-4-pyrimidinone-2′-deoxyriboside
  作者：Stéphanie Gourdain、Christian Petermann、Agathe Martinez、Dominique Harakat、Pascale Clivio

  DOI：10.1021/jo102316r

  日期：2011.3.18

  The 2-azido analogue of 2'-deoxyuridine was prepared in three steps from 2'-deoxy-2-thiouridine. The sulfur atom of the 2-thio nucleoside was methylated and then displaced by hydrazine to furnish the corresponding 2-hydrazino derivative. After diazotization, the 2-azido compound that exists as its tetrazolo tautomer was obtained. Upon UV irradiation in aqueous solution, the title compound led to isocytosine.