1-Boc-3-fluoro-3-(4-methoxyphenoxymethyl)azetidine | 1126650-64-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-Boc-3-fluoro-3-(4-methoxyphenoxymethyl)azetidine
• 英文别名: Tert-butyl 3-fluoro-3-[(4-methoxyphenoxy)methyl]azetidine-1-carboxylate
• CAS: 1126650-64-3
• 化学式: C₁₆H₂₂FNO₄
• 分子量: 311.353
• InChiKey: GSXXDKIJZXZPAA-UHFFFAOYSA-N

物化性质

• 熔点：
  53 °C
• 沸点：
  400.6±35.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-Boc-3-fluoro-3-(4-methoxyphenoxymethyl)azetidine 在 ammonium cerium (IV) nitrate 、 水 作用下， 以 乙腈 为溶剂， 以74%的产率得到3-氟-3-(羟甲基)氮杂环丁烷-1-羧酸叔丁酯
  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
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 1-diphenylmethyl-3-fluoro-3-(4-methoxyphenoxymethyl)azetidine 在 palladium on carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、400.01 kPa 条件下， 反应 48.0h， 以62%的产率得到1-Boc-3-fluoro-3-(4-methoxyphenoxymethyl)azetidine
  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.