1-N-phenylinosine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 1-N-phenylinosine
• 英文别名: 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-phenylpurin-6-one
• 化学式: C₁₆H₁₆N₄O₅
• 分子量: 344.327
• InChiKey: VPJOKAKDYRRELK-XNIJJKJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2',3',5'-tris-O-(tert-butyldimethylsilyl)inosine 在 4 A molecular sieve 、 copper diacetate 吡啶 、 吡啶-N-氧化物 、 四丁基氟化铵 、 氧气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成 1-N-phenylinosine
  参考文献：
  名称：

  Copper catalyzed arylation with boronic acids for the synthesis of N1-aryl purine nucleosides

  摘要：

  The synthesis of a series of N-1-aryl inosine and guanosine derivatives is described. The procedure for chemoselective N-1-arylation involves the mild oxidative copper(II) mediated coupling with boronic acids. This approach provides access to substituted N-1-aryl purines with interesting structural characteristics and novel scaffolds for drug discovery. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.083

文献信息

• Synthesis of<i>N</i>-Arylinosines
  作者：Tokumi Maruyama、Yoshiko Sato、Takeshi Goto、Mitsutoshi Fukuhara

  DOI：10.1080/07328319708006136

  日期：1997.7

  2',3',5'-Tri-O(tetrahydropyran-2-yl)inosine 1 was treated with iodobenzene or 2-bromopyridine in the presence of cuprous oxide in pyridines to give the N-1-aryl derivatives 2a,b. Deprotection of the products afforded N-1-arylinosines 3a,b.
• Copper catalyzed arylation with boronic acids for the synthesis of N1-aryl purine nucleosides
  作者：J. Jacob Strouse、Marjan Jeselnik、Frederick Tapaha、Colleen B. Jonsson、William B. Parker、Jeffrey B. Arterburn

  DOI：10.1016/j.tetlet.2005.06.083

  日期：2005.8

  The synthesis of a series of N-1-aryl inosine and guanosine derivatives is described. The procedure for chemoselective N-1-arylation involves the mild oxidative copper(II) mediated coupling with boronic acids. This approach provides access to substituted N-1-aryl purines with interesting structural characteristics and novel scaffolds for drug discovery. (c) 2005 Elsevier Ltd. All rights reserved.