2-azido-4-hydroxymethyl-cyclopentanol | 648893-61-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azido-4-hydroxymethyl-cyclopentanol
• 英文别名: (+/-)-2-azido-4-hydroxymethylcyclopentan-1-ol；(1R,2R,4S)-2-azido-4-(hydroxymethyl)cyclopentan-1-ol
• CAS: 648893-61-2
• 化学式: C₆H₁₁N₃O₂
• 分子量: 157.172
• InChiKey: RSIWMGCBAWDFKX-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-azido-4-hydroxymethyl-cyclopentanol 在 氨 作用下， 以 甲醇 为溶剂， 反应 32.0h， 生成 1-(2-hydroxy-4-hydroxymethyl-cyclopentyl)-1H-[1,2,3]triazole-4-carboxylic acid amide
  参考文献：
  名称：

  Synthesis of 1,2,3-triazolo-carbanucleoside analogues of ribavirin targeting an HCV in replicon

  摘要：

  The synthesis of carbocyclic and phosphonocarbocyclic analogues of ribavirin, an anti-HCV inhibitor, are described. Those compounds were evaluated against HCV but also against other important viruses in order to determine their spectrum of antiviral activity. Compounds 6 and 13 displayed a moderate IC50 against HIV-1 of 43.8 and 37 muM, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00349-3
• 作为产物：
  描述：

  anti-3-(Hydroxymethyl)-6-oxabicyclo<3.1.0>hexane 在 sodium azide 作用下， 以 甲醇 、 水 为溶剂， 反应 15.0h， 以79%的产率得到2-azido-4-hydroxymethyl-cyclopentanol
  参考文献：
  名称：

  Synthesis of 1,2,3-triazolo-carbanucleoside analogues of ribavirin targeting an HCV in replicon

  摘要：

  The synthesis of carbocyclic and phosphonocarbocyclic analogues of ribavirin, an anti-HCV inhibitor, are described. Those compounds were evaluated against HCV but also against other important viruses in order to determine their spectrum of antiviral activity. Compounds 6 and 13 displayed a moderate IC50 against HIV-1 of 43.8 and 37 muM, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00349-3

文献信息

• Efficient Pd(0)-catalyzed synthesis of 1,2,3-triazolo-3′-deoxycarbanucleosides and their analogues
  作者：Nicolas Joubert、Raymond F. Schinazi、Luigi A. Agrofoglio

  DOI：10.1016/j.tet.2005.09.034

  日期：2005.12

  The racemic synthesis of hitherto unknown 5-substituted-[1,2,3]-triazolo-3'-deoxycarbanucleosides and [1,2,3]-triazolo-[4,5-c] pyridin-4-one analogues is described. The key iodinated intermediate 10 was prepared in 10 steps using a malonic synthesis. Various alkynes were introduced at the C-5 position of 10 under optimized Pd(0)-catalyzed Sonogashira cross-coupling alkyrylation to yield after deprotection 12a-i. The synthesis of their 8-aza-3-deazapurine analogues (13a-h) was also accomplished through the heteroannulation of internal alkynes under aqueous dimethylamine. (c) 2005 Elsevier Ltd. All rights reserved.