3-fluoro-3-phenylazetidinium trifluoroacetate | 1126650-57-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: 3-fluoro-3-phenylazetidinium trifluoroacetate
• 英文别名: 3-Fluoro-3-phenylazetidine;2,2,2-trifluoroacetic acid
• CAS: 1126650-57-4
• 化学式: C₂HF₃O₂*C₉H₁₀FN
• 分子量: 265.207
• InChiKey: WPKNJFKHAUMCTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  tert-butyl 3-fluoro-3-phenylazetidine-1-carboxylate 、 三氟乙酸 以 乙醚 为溶剂， 反应 72.0h， 以52%的产率得到3-fluoro-3-phenylazetidinium trifluoroacetate
  参考文献：
  名称：

  Synthesis of 1-Boc-3-fluoroazetidine-3-carboxylic Acid

  摘要：

  Synthetic strategies toward 3-fluoroazetidine-3-carboxylic acid, a new cyclic fluorinated beta-amino acid with high potential as building block in medicinal chemistry, were evaluated. The successful pathway includes the bromofluorination of N-(diphenylmethylidcne)-2-(4-methoxyphenoxymethyl)-2-propenylamine, yielding 1-diphenylmethyl-3-hydroxymethyl-3-fluoroazetidine after reduction of the imino bond, ring closure, and removal of the 4-methoxybenzyl group. Changing the N-protecting group to a Boc-group allows further oxidation to 1-Boc-3-fluoroazetidine3-carboxylic acid, a new fluorinated heterocyclic amino acid.

  DOI：

  10.1021/jo802791r

文献信息

• Synthesis of 1-Boc-3-fluoroazetidine-3-carboxylic Acid
  作者：Eva Van Hende、Guido Verniest、Frederik Deroose、Jan-Willem Thuring、Gregor Macdonald、Norbert De Kimpe

  DOI：10.1021/jo802791r

  日期：2009.3.6

  Synthetic strategies toward 3-fluoroazetidine-3-carboxylic acid, a new cyclic fluorinated beta-amino acid with high potential as building block in medicinal chemistry, were evaluated. The successful pathway includes the bromofluorination of N-(diphenylmethylidcne)-2-(4-methoxyphenoxymethyl)-2-propenylamine, yielding 1-diphenylmethyl-3-hydroxymethyl-3-fluoroazetidine after reduction of the imino bond, ring closure, and removal of the 4-methoxybenzyl group. Changing the N-protecting group to a Boc-group allows further oxidation to 1-Boc-3-fluoroazetidine3-carboxylic acid, a new fluorinated heterocyclic amino acid.