Methyl 3-(Diisopropylcarbamoyl)isonicotinate | 139260-68-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Methyl 3-(Diisopropylcarbamoyl)isonicotinate
• 英文别名: methyl 3-[di(propan-2-yl)carbamoyl]pyridine-4-carboxylate
• CAS: 139260-68-7
• 化学式: C₁₄H₂₀N₂O₃
• 分子量: 264.324
• InChiKey: GMTQYHBRZGDDRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.5
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Methyl 3-(Diisopropylcarbamoyl)isonicotinate 在 盐酸 、 正丁基锂 、 甲酸 、 锌 作用下， 以 乙醚 为溶剂， 反应 50.0h， 生成 4-<1-(5-Methoxy-1-phenylsulphonylindol-2-yl)ethyl>nicotinic Acid
  参考文献：
  名称：

  Synthesis of 11-amino-substituted-9-methoxy-5-methyl-6H-pyrido[4,3-b]-carbazoles

  摘要：

  A route to 11-amino-substituted-6H-pyrido[4,3-b]carbazoles has been studied. Thus, condensation of 2-(4-lithiopyridine-3-yl)-4,4-dimethyloxazoline with 2-acetyl-5-methoxy-1-phenylsulphonylindole led to a low yield of the expected alcohol, which upon hydrolysis gave a complex mixture. A better starting building block was 4-acetyl-N,N-diisopropylnicotinamide obtained either from N,N-diisopropyl-4-lithionicotinamide (low yield) or from pyridine-3,4-dicarboxylic anhydride, using a 4-step sequence. This compound was treated with 2-lithio-5-methoxy-1-phenylsulphonylindole, affording N,N-diisopropyl-4-[1-(5-methoxy-1-phenylsulphonylindol-2-yl)-1-hydroxyethyl]nicotinamide. Hydrolysis and then reduction led to 4-[1-(5-methoxy-1-phenylsulphonylindol-2-yl)-ethyl]nicotinic acid whose amides were cyclized by phosphorus trichlorideoxide. Finally, the title compounds were obtained by Raney-nickel reduction-elimination of the 6-phenylsulphonyl protecting group.

  DOI：

  10.1039/p19910003165
• 作为产物：
  描述：

  吡啶-3,4-二甲酸酐 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 37.5h， 生成 Methyl 3-(Diisopropylcarbamoyl)isonicotinate
  参考文献：
  名称：

  Synthesis of 11-amino-substituted-9-methoxy-5-methyl-6H-pyrido[4,3-b]-carbazoles

  摘要：

  A route to 11-amino-substituted-6H-pyrido[4,3-b]carbazoles has been studied. Thus, condensation of 2-(4-lithiopyridine-3-yl)-4,4-dimethyloxazoline with 2-acetyl-5-methoxy-1-phenylsulphonylindole led to a low yield of the expected alcohol, which upon hydrolysis gave a complex mixture. A better starting building block was 4-acetyl-N,N-diisopropylnicotinamide obtained either from N,N-diisopropyl-4-lithionicotinamide (low yield) or from pyridine-3,4-dicarboxylic anhydride, using a 4-step sequence. This compound was treated with 2-lithio-5-methoxy-1-phenylsulphonylindole, affording N,N-diisopropyl-4-[1-(5-methoxy-1-phenylsulphonylindol-2-yl)-1-hydroxyethyl]nicotinamide. Hydrolysis and then reduction led to 4-[1-(5-methoxy-1-phenylsulphonylindol-2-yl)-ethyl]nicotinic acid whose amides were cyclized by phosphorus trichlorideoxide. Finally, the title compounds were obtained by Raney-nickel reduction-elimination of the 6-phenylsulphonyl protecting group.

  DOI：

  10.1039/p19910003165