4-nitro-2-(β-D-ribofuranosyl)-2H-indazole | 28083-98-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 4-nitro-2-(β-D-ribofuranosyl)-2H-indazole
• 英文别名: 1-(4-nitro-indazol-2-yl)-β-D-1-deoxy-ribofuranose；2-(β-D-ribofuranosyl)-4-nitroindazol；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(4-nitroindazol-2-yl)oxolane-3,4-diol
• CAS: 28083-98-9
• 化学式: C₁₂H₁₃N₃O₆
• 分子量: 295.252
• InChiKey: PXAQQSLSQBCJFG-DDHJBXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-硝基吲唑 在 ammonium sulfate 、 氨 、 六甲基二硅氮烷 作用下， 以 甲醇 为溶剂， 反应 25.0h， 生成 4-nitro-2-(β-D-ribofuranosyl)-2H-indazole
  参考文献：
  名称：

  Regioselective Synthesis of Indazole N ¹‐ and N ²‐(β‐d‐Ribonucleosides)

  摘要：

  The regioselective synthesis of 4-nitroindazole N-1- and N-2- (beta-D-ribonucleosides) (8, 9, 1b and 2b) is described. The N-1-regioisomers are formed under thermodynamic control of the glycosylation reaction [fusion reaction or Silyl Hilbert-Johnson glycosylation for 48 h (66%)], while the kinetic control (Silyl Hilbert-Johnson glycosylation for 5 h) afforded only the N-2-isomer (64%). The structures of the nucleosides 1b and 2b were assigned by single crystal X-ray analyses. The 4-amino-N-1-(beta-D-ribofuranosyl)-1H-indazole (3b) was obtained from the nitro nucleoside 1b by catalytic hydrogenation. Compound 3b shows fluorescence while the 4-nitroindazole nucleosides 1b and 2b do not possess this property.

  DOI：

  10.1081/ncn-120027830

文献信息

• Regioselective Synthesis of Indazole <i>N</i> ¹‐ and <i>N</i> ²‐(<i>β</i>‐<scp>d</scp>‐Ribonucleosides)
  作者：Frank Seela、Xiaohua Peng

  DOI：10.1081/ncn-120027830

  日期：2004.1.1

  The regioselective synthesis of 4-nitroindazole N-1- and N-2- (beta-D-ribonucleosides) (8, 9, 1b and 2b) is described. The N-1-regioisomers are formed under thermodynamic control of the glycosylation reaction [fusion reaction or Silyl Hilbert-Johnson glycosylation for 48 h (66%)], while the kinetic control (Silyl Hilbert-Johnson glycosylation for 5 h) afforded only the N-2-isomer (64%). The structures of the nucleosides 1b and 2b were assigned by single crystal X-ray analyses. The 4-amino-N-1-(beta-D-ribofuranosyl)-1H-indazole (3b) was obtained from the nitro nucleoside 1b by catalytic hydrogenation. Compound 3b shows fluorescence while the 4-nitroindazole nucleosides 1b and 2b do not possess this property.