4-(2-bromo-6-methoxyphenyl)morpholine | 1444746-97-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 4-(2-bromo-6-methoxyphenyl)morpholine
• CAS: 1444746-97-7
• 化学式: C₁₁H₁₄BrNO₂
• 分子量: 272.142
• InChiKey: MVDSHYYDEWZYIA-UHFFFAOYSA-N

物化性质

• 沸点：
  358.6±42.0 °C(Predicted)
• 密度：
  1.410±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-溴吗啉 、 三氟甲烷磺酸3-甲氧基-2-(三甲基硅基)苯酯 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 4-(2-bromo-3-methoxyphenyl)morpholine 、 4-(2-bromo-6-methoxyphenyl)morpholine
  参考文献：
  名称：

  Synthesis of ortho-Haloaminoarenes by Aryne Insertion of Nitrogen–Halide Bonds

  摘要：

  A rapid and general access to ortho-haloaminoarenes has been developed by aryne insertion into N-chloramine, N-bromoamine, and N-iodoamine bonds via two complementary protocols harnessing fluoride-promoted 1,2-elimination of ortho-trimethylsilyl aryltriflates. Typically, electron-deficient N-chloramines effectively react with aryne intermediates generated at elevated temperature with CsF, while less stable N-haloamines are found more efficient under milder, TBAF-mediated aryne formation at room temperature. Both protocols demonstrate a good level of regioselectivity and functional group tolerance. Efforts to elucidate the mechanism of NX insertion are also discussed. The practical value of this transformation is highlighted by rapid synthesis of novel analogues of the antipsychotic cariprazine.

  DOI：

  10.1021/jo502541t