methyl 3-{2-[2-N-(Boc)aminophenyl]-5-methyl-1H-pyrrolyl}propanoate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 3-{2-[2-N-(Boc)aminophenyl]-5-methyl-1H-pyrrolyl}propanoate
• 英文别名: Methyl 3-[2-methyl-5-[2-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]pyrrol-1-yl]propanoate；methyl 3-[2-methyl-5-[2-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]pyrrol-1-yl]propanoate
• 化学式: C₂₀H₂₆N₂O₄
• 分子量: 358.437
• InChiKey: UOYZAQZBBDDONK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻氨基苯甲酸甲酯 在 氧气 、 sodium acetate 、 copper(l) cyanide 、 溶剂黄146 、 copper(l) chloride 、 palladium dichloride 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 237.0h， 生成 methyl 3-{2-[2-N-(Boc)aminophenyl]-5-methyl-1H-pyrrolyl}propanoate
  参考文献：
  名称：

  Aminophenylpyrrole Synthesis and Application to Pyrrolo[1,2-c]quinazolinone Synthesis

  摘要：

  Aminophenylpyrroles have been synthesized by a three-step route from methyl N-(Boc)anthranilate (2). Amine protection of commercially available methyl anthranilate (1) gave Boc-protected methyl ester 2, which reacted with vinylmagnesium bromide in the presence of a catalytic amount of copper (I) cyanide to yield 1-[2-N-(Boc)aminophenyl]pent-4-en-1-one (3) in 43% yield. Oxidation of homoallylic ketone 3 using either a mixture of OsO4 center dot NaIO4 and 2,6-lutidine, or PdCl2-CuCl under oxygen atmosphere gave respectively aldehyde 4 and ketone 5. Treatment of 1,4-dicarbonyl compounds 4 and 5 with ammonium formate as well as primary amines under Paal-Knorr conditions afforded a set of eight 2-[2-N-(Boc)aminophenyl]pyrroles 6a-d and 7a-d. In addition, treatment of 2-[2-N-(Boc)aminophenyl]-1H-pyrrole 6a with NaH provided a novel entry to pyrrolo [1,2-c]quinazolin-5(6H)-one 8.

  DOI：

  10.3987/com-13-s(s)73

文献信息

• Aminophenylpyrrole Synthesis and Application to Pyrrolo[1,2-c]quinazolinone Synthesis
  作者：William D. Lubell、Aurélie A. Dörr

  DOI：10.3987/com-13-s(s)73

  日期：——

  Aminophenylpyrroles have been synthesized by a three-step route from methyl N-(Boc)anthranilate (2). Amine protection of commercially available methyl anthranilate (1) gave Boc-protected methyl ester 2, which reacted with vinylmagnesium bromide in the presence of a catalytic amount of copper (I) cyanide to yield 1-[2-N-(Boc)aminophenyl]pent-4-en-1-one (3) in 43% yield. Oxidation of homoallylic ketone 3 using either a mixture of OsO4 center dot NaIO4 and 2,6-lutidine, or PdCl2-CuCl under oxygen atmosphere gave respectively aldehyde 4 and ketone 5. Treatment of 1,4-dicarbonyl compounds 4 and 5 with ammonium formate as well as primary amines under Paal-Knorr conditions afforded a set of eight 2-[2-N-(Boc)aminophenyl]pyrroles 6a-d and 7a-d. In addition, treatment of 2-[2-N-(Boc)aminophenyl]-1H-pyrrole 6a with NaH provided a novel entry to pyrrolo [1,2-c]quinazolin-5(6H)-one 8.