tert-butyl 2-(5-bromo-2-oxopyridin-1(2H)-yl)propanoate

• 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: tert-butyl 2-(5-bromo-2-oxopyridin-1(2H)-yl)propanoate
• 英文别名: Tert-butyl 2-(5-bromo-2-oxopyridin-1-yl)propanoate
• 化学式: C₁₂H₁₆BrNO₃
• 分子量: 302.168
• InChiKey: RNOUVJCFEFKPOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴丙酸叔丁酯 、 2-羟基-5-溴吡啶 在 potassium carbonate 作用下， 以 水 为溶剂， 反应 18.0h， 以75%的产率得到tert-butyl 2-(5-bromo-2-oxopyridin-1(2H)-yl)propanoate
  参考文献：
  名称：

  Mild and Regioselective N-Alkylation of 2-Pyridones in Water

  摘要：

  A mild and regioselective N-alkylation reaction of 2-pyridones in water has been developed. Tween 20 (2% w/w) was added to create a micellar system for improved solubility of starting materials, which leads to enhanced reaction rates. The protocol demonstrated a wide substrate scope with good isolated yield's (40-94%) for all of the 24 examples evaluated. High regioselectivity favoring N-alkylation over O-alkylation was observed for benzyl halides (>5:1), primary alkyl halides (>6:1), and bulky and less reactive secondary alkyl halides (>2.4:1).

  DOI：

  10.1021/acs.orglett.5b01628

文献信息

• Mild and Regioselective <i>N</i>-Alkylation of 2-Pyridones in Water
  作者：Xin Hao、Zhongmiao Xu、Hongfu Lu、Xuedong Dai、Ting Yang、Xichen Lin、Feng Ren

  DOI：10.1021/acs.orglett.5b01628

  日期：2015.7.17

  A mild and regioselective N-alkylation reaction of 2-pyridones in water has been developed. Tween 20 (2% w/w) was added to create a micellar system for improved solubility of starting materials, which leads to enhanced reaction rates. The protocol demonstrated a wide substrate scope with good isolated yield's (40-94%) for all of the 24 examples evaluated. High regioselectivity favoring N-alkylation over O-alkylation was observed for benzyl halides (>5:1), primary alkyl halides (>6:1), and bulky and less reactive secondary alkyl halides (>2.4:1).