N-({4-[hydroxy(4-methoxyphenyl)methyl]pyridin-3-yl}methyl)pivalamide | 1570232-46-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-({4-[hydroxy(4-methoxyphenyl)methyl]pyridin-3-yl}methyl)pivalamide
• 英文别名: N-[[4-[hydroxy-(4-methoxyphenyl)methyl]pyridin-3-yl]methyl]-2,2-dimethylpropanamide
• CAS: 1570232-46-0
• 化学式: C₁₉H₂₄N₂O₃
• 分子量: 328.411
• InChiKey: GTZMDZBOWRVUJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  71.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-氨甲基吡啶 在 叔丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 正戊烷 为溶剂， 反应 5.5h， 生成 N-({4-[hydroxy(4-methoxyphenyl)methyl]pyridin-3-yl}methyl)pivalamide
  参考文献：
  名称：

  Control of Site of Lithiation of 3-(Aminomethyl)pyridine Derivatives

  摘要：

  Lithiation of N-(pyridin-3-ylmethyl)pivalamide, tert-butyl N-(pyridin-3-ylmethyl)carbamate, and N,N-dimethyl-N-(pyridin-3-ylmethyl)urea with tert-butyllithium (3 equiv) in anhydrous tetrahydrofuran at -78 degrees C takes place on the nitrogen and on the ring at the 4-position. The dilithium reagents thus obtained react with various electrophiles to give the corresponding substituted derivatives in high yields. On the other hand, regioselective side-chain lithiation occurs with lithium diisopropylamide (3.3 equiv) at -20 to 0 degrees C. A mixture of ring and side-chain substitution products is obtained with n-butyllithium as the lithium reagent. Treatment of one of the ring-substituted products with trifluoroacetic anhydride in dichloromethane under reflux conditions led to formation of the corresponding 1H-pyrrolo[3,4-c]pyridine in high yield.

  DOI：

  10.1055/s-0033-1338547

文献信息

• Control of Site of Lithiation of 3-(Aminomethyl)pyridine Derivatives
  作者：Keith Smith、Gamal El-Hiti、Mohammed Alshammari、Ahmed Fekri

  DOI：10.1055/s-0033-1338547

  日期：——

  Lithiation of N-(pyridin-3-ylmethyl)pivalamide, tert-butyl N-(pyridin-3-ylmethyl)carbamate, and N,N-dimethyl-N-(pyridin-3-ylmethyl)urea with tert-butyllithium (3 equiv) in anhydrous tetrahydrofuran at -78 degrees C takes place on the nitrogen and on the ring at the 4-position. The dilithium reagents thus obtained react with various electrophiles to give the corresponding substituted derivatives in high yields. On the other hand, regioselective side-chain lithiation occurs with lithium diisopropylamide (3.3 equiv) at -20 to 0 degrees C. A mixture of ring and side-chain substitution products is obtained with n-butyllithium as the lithium reagent. Treatment of one of the ring-substituted products with trifluoroacetic anhydride in dichloromethane under reflux conditions led to formation of the corresponding 1H-pyrrolo[3,4-c]pyridine in high yield.