1-azidomethyl-1-fluorocyclopentane | 1462885-78-4

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1-azidomethyl-1-fluorocyclopentane
• 英文别名: 1-(Azidomethyl)-1-fluorocyclopentane；1-(azidomethyl)-1-fluorocyclopentane
• CAS: 1462885-78-4
• 化学式: C₆H₁₀FN₃
• 分子量: 143.164
• InChiKey: KMLPRWUWBRZJGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  10.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  48.76
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-azidomethyl-1-fluorocyclopentane 在 palladium on carbon 、 氢气 、 盐酸 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、500.01 kPa 条件下， 反应 16.17h， 以58%的产率得到(1-氟环戊基)甲胺盐酸盐
  参考文献：
  名称：

  A convenient approach towards the 1-aminomethyl-1-fluorocycloalkane scaffold

  摘要：

  A three-step synthesis towards 1-aminomethy1-1-fluorocycloalkanes was developed starting from methylenecycloalkanes. Methylenecyclobutane, methylenecyclopentane and methylenecyclohexane were first bromofluorinated to provide the corresponding Markovnikov products, 1-bromomethy1-1-fluorocycloalkanes, which were then converted towards the title compound via azide substitution and hydrogenation. The bromofluorination of methylenecyclopropane, however, led to both the Markovnikov and the anti-Markovnikov product. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.127
• 作为产物：
  描述：

  1-(bromomethyl)-1-fluorocyclopentane 在 sodium azide 、 sodium iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以68%的产率得到1-azidomethyl-1-fluorocyclopentane
  参考文献：
  名称：

  A convenient approach towards the 1-aminomethyl-1-fluorocycloalkane scaffold

  摘要：

  A three-step synthesis towards 1-aminomethy1-1-fluorocycloalkanes was developed starting from methylenecycloalkanes. Methylenecyclobutane, methylenecyclopentane and methylenecyclohexane were first bromofluorinated to provide the corresponding Markovnikov products, 1-bromomethy1-1-fluorocycloalkanes, which were then converted towards the title compound via azide substitution and hydrogenation. The bromofluorination of methylenecyclopropane, however, led to both the Markovnikov and the anti-Markovnikov product. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.127