1-fluoro-5-iodopentan-2-yl acetate | 153780-73-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-fluoro-5-iodopentan-2-yl acetate
• 英文别名: (1-fluoro-5-iodopentan-2-yl) acetate
• CAS: 153780-73-5
• 化学式: C₇H₁₂FIO₂
• 分子量: 274.074
• InChiKey: NHLYKLHLPUDMSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-fluoro-5-iodopentan-2-yl acetate 在 4-二甲氨基吡啶 、 18-冠醚-6 、 氨 、 potassium carbonate 、 三乙胺 、 cesium fluoride 、 三丁基氧化锡 作用下， 以 甲醇 为溶剂， 反应 167.0h， 生成 2-amino-6-chloro-7-(1'-fluoro-5'-pivaloyloxypentan-2'-yl)-7H-purine
  参考文献：
  名称：

  9-(1-Fluoro-5-hydroxypentan-2-yl)-9H-guanine: synthesis and evaluation of antiviral activity

  摘要：

  5-Fluoro-4-tosyloxypentyl pivalate has been synthesized in four steps from 2-(fluoromethyl)tetrahydrofuran. Condensation with 2-amino-6-chloropurine gave the N-9 derivative, which was converted via the 6-methoxy analogue into 9-(1-fluoro-5-hydroxypentan-2-yl)-9H-guanine. The latter was evaluated, and found inactive, in a large variety of antiviral assays.

  DOI：

  10.1039/p19930002107
• 作为产物：
  描述：

  2-(fluoromethyl)tetrahydrofuran 、 乙酰氯 在 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 65.0h， 以82%的产率得到1-fluoro-5-iodopentan-2-yl acetate
  参考文献：
  名称：

  9-(1-Fluoro-5-hydroxypentan-2-yl)-9H-guanine: synthesis and evaluation of antiviral activity

  摘要：

  5-Fluoro-4-tosyloxypentyl pivalate has been synthesized in four steps from 2-(fluoromethyl)tetrahydrofuran. Condensation with 2-amino-6-chloropurine gave the N-9 derivative, which was converted via the 6-methoxy analogue into 9-(1-fluoro-5-hydroxypentan-2-yl)-9H-guanine. The latter was evaluated, and found inactive, in a large variety of antiviral assays.

  DOI：

  10.1039/p19930002107

文献信息

• Fluorinated Carbaacyclonucleosides: Synthesis and Evaluation of Antiviral Activity
  作者：Maureen Lewis、T. Brian H. McMurry、Erik De Clercq

  DOI：10.1080/15257779508010714

  日期：1995.11

  Two series of fluoroacyclic nucleosides were synthesised by condensation of nucleic acid bases with substituted fluoropentanes. 1-(5'-Fluoro-4'-hydroxypentyl)-cytosine showed a modest activity against cytomegalovirus (MIC(50): 12-15 mu g/ml). All the other compounds were inactive against all the viruses tested.