5-methoxycarbonyl-4-(2-methoxy-2-oxoethyl)-3-methyl-1H-pyrrole-2-carboxylic acid | 202057-95-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-methoxycarbonyl-4-(2-methoxy-2-oxoethyl)-3-methyl-1H-pyrrole-2-carboxylic acid
• CAS: 202057-95-2
• 化学式: C₁₁H₁₃NO₆
• 分子量: 255.227
• InChiKey: CJOROZFCYBVSRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-methoxycarbonyl-4-(2-methoxy-2-oxoethyl)-3-methyl-1H-pyrrole-2-carboxylic acid 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 碘 、 sodium acetate 、 碳酸氢钠 、 对甲苯磺酸 、 potassium iodide 、 diborane(6) 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醇 、 氯仿 、 水 为溶剂， 25.0~110.0 ℃ 、344.73 kPa 条件下， 反应 35.0h， 生成 2,8-di(2-acetoxyethyl)-3,7-dimethyl-5-phenyldipyrrylmethane-1,9-dicarboxylic acid
  参考文献：
  名称：

  Concerning the Synthesis of 3,7,13,17-Tetramethyl-5,15-diphenylporphyrin, a Sterically Hindered Porphyrin

  摘要：

  The synthesis of the sterically hindered porphyrin 1 (3,7,13,17-tetramethyl-5,15-diphenylporphyrin) could only be achieved by first preparing a 5,16-meso substituted octaalkylporphyrin. Thus, the synthesis of a 2,8,12,18-tetrakis(2-hydroxyethyl)-3,7,17-tetramethyl-5,15-diphenylprophyrin (12) had to precede the synthesis of 1. The 2-hydroxyethyl side chains were then converted into vinyl residues via the corresponding 2-chloroethyl intermediates. The four vinyl residues (at C2, C8, C12, C18) were cleaved using a resorcinol melt, and the tetra beta-unsubstituted porphyrin 1 was then obtained. Porphyrin 1 could not be prepared by direct condensation of benzaldehyde with 3-methylpyrrole nor with a meso phenyl beta-unsubstituted dipyrrylmethane.

  DOI：

  10.1021/jo971807l
• 作为产物：
  描述：

  5-O-benzyl 2-O-methyl 3-(2-methoxy-2-oxoethyl)-4-methyl-1H-pyrrole-2,5-dicarboxylate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以68%的产率得到5-methoxycarbonyl-4-(2-methoxy-2-oxoethyl)-3-methyl-1H-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  Concerning the Synthesis of 3,7,13,17-Tetramethyl-5,15-diphenylporphyrin, a Sterically Hindered Porphyrin

  摘要：

  The synthesis of the sterically hindered porphyrin 1 (3,7,13,17-tetramethyl-5,15-diphenylporphyrin) could only be achieved by first preparing a 5,16-meso substituted octaalkylporphyrin. Thus, the synthesis of a 2,8,12,18-tetrakis(2-hydroxyethyl)-3,7,17-tetramethyl-5,15-diphenylprophyrin (12) had to precede the synthesis of 1. The 2-hydroxyethyl side chains were then converted into vinyl residues via the corresponding 2-chloroethyl intermediates. The four vinyl residues (at C2, C8, C12, C18) were cleaved using a resorcinol melt, and the tetra beta-unsubstituted porphyrin 1 was then obtained. Porphyrin 1 could not be prepared by direct condensation of benzaldehyde with 3-methylpyrrole nor with a meso phenyl beta-unsubstituted dipyrrylmethane.

  DOI：

  10.1021/jo971807l

文献信息

• Concerning the Synthesis of 3,7,13,17-Tetramethyl-5,15-diphenylporphyrin, a Sterically Hindered Porphyrin
  作者：Aldonia Valasinas、Jorge Hurst、Benjamin Frydman

  DOI：10.1021/jo971807l

  日期：1998.2.1

  The synthesis of the sterically hindered porphyrin 1 (3,7,13,17-tetramethyl-5,15-diphenylporphyrin) could only be achieved by first preparing a 5,16-meso substituted octaalkylporphyrin. Thus, the synthesis of a 2,8,12,18-tetrakis(2-hydroxyethyl)-3,7,17-tetramethyl-5,15-diphenylprophyrin (12) had to precede the synthesis of 1. The 2-hydroxyethyl side chains were then converted into vinyl residues via the corresponding 2-chloroethyl intermediates. The four vinyl residues (at C2, C8, C12, C18) were cleaved using a resorcinol melt, and the tetra beta-unsubstituted porphyrin 1 was then obtained. Porphyrin 1 could not be prepared by direct condensation of benzaldehyde with 3-methylpyrrole nor with a meso phenyl beta-unsubstituted dipyrrylmethane.