Ethyl 5-<(4-methylphenyl)hydroxymethyl>pyrrole-2-carboxylate | 152999-74-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: Ethyl 5-<(4-methylphenyl)hydroxymethyl>pyrrole-2-carboxylate
• CAS: 152999-74-1
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: JSULYQUWRBDGLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  62.32
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Ethyl 5-<(4-methylphenyl)hydroxymethyl>pyrrole-2-carboxylate 在 sodium hydroxide 、 乙酸酐 作用下， 以 乙二醇 、 溶剂黄146 为溶剂， 反应 3.25h， 生成 5-(4-methylphenyl)dipyrromethane
  参考文献：
  名称：

  Rational tetraarylporphyrin syntheses: tetraarylporphyrins from the MacDonald route

  摘要：

  Four new synthetic routes to meso-tetraarylporphyrins using a MacDonald-type 2 + 2 condensation are described. Self-condensation of a 5-aryldipyrromethane (e.g., 17) with an aryl-substituted one-carbon bridging unit affords a mixture of tetraarylporphyrins due to acid-catalyzed redistribution reactions. The second and third methods presented here show wide applicability for the preparation of 5,10,15,20-tetraaryl-substituted porphyrins (e.g., 31, 37, 48, 49) with 2-fold rotational symmetry and involve self-condensation of 5-aryl-1-aryldipyrromethanecarbinols. Finally, the fourth approach involves a 2 + 2 approach in which one of the two dipyrromethanes bears both of the bridging carbons in the porphyrin products, affording porphyrin 50 which possesses three different aryl rings, with one pair of uniquely opposite identical aryl groups. The last two 2 + 2 methods are further extended to give a tetraarylporphyrin 38 bearing four different aryl groups in a predesignated array, the structure of which is confirmed by a single-crystal X-ray study.

  DOI：

  10.1021/jo00077a056
• 作为产物：
  描述：

  5-甲酰基-1H-吡咯-2-甲酸乙酯 、 对甲苯基溴化镁 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.5h， 以98%的产率得到Ethyl 5-<(4-methylphenyl)hydroxymethyl>pyrrole-2-carboxylate
  参考文献：
  名称：

  Rational tetraarylporphyrin syntheses: tetraarylporphyrins from the MacDonald route

  摘要：

  Four new synthetic routes to meso-tetraarylporphyrins using a MacDonald-type 2 + 2 condensation are described. Self-condensation of a 5-aryldipyrromethane (e.g., 17) with an aryl-substituted one-carbon bridging unit affords a mixture of tetraarylporphyrins due to acid-catalyzed redistribution reactions. The second and third methods presented here show wide applicability for the preparation of 5,10,15,20-tetraaryl-substituted porphyrins (e.g., 31, 37, 48, 49) with 2-fold rotational symmetry and involve self-condensation of 5-aryl-1-aryldipyrromethanecarbinols. Finally, the fourth approach involves a 2 + 2 approach in which one of the two dipyrromethanes bears both of the bridging carbons in the porphyrin products, affording porphyrin 50 which possesses three different aryl rings, with one pair of uniquely opposite identical aryl groups. The last two 2 + 2 methods are further extended to give a tetraarylporphyrin 38 bearing four different aryl groups in a predesignated array, the structure of which is confirmed by a single-crystal X-ray study.

  DOI：

  10.1021/jo00077a056

文献信息

• Rational tetraarylporphyrin syntheses: tetraarylporphyrins from the MacDonald route
  作者：David M. Wallace、Sam H. Leung、Mathias O. Senge、Kevin M. Smith

  DOI：10.1021/jo00077a056

  日期：1993.12

  Four new synthetic routes to meso-tetraarylporphyrins using a MacDonald-type 2 + 2 condensation are described. Self-condensation of a 5-aryldipyrromethane (e.g., 17) with an aryl-substituted one-carbon bridging unit affords a mixture of tetraarylporphyrins due to acid-catalyzed redistribution reactions. The second and third methods presented here show wide applicability for the preparation of 5,10,15,20-tetraaryl-substituted porphyrins (e.g., 31, 37, 48, 49) with 2-fold rotational symmetry and involve self-condensation of 5-aryl-1-aryldipyrromethanecarbinols. Finally, the fourth approach involves a 2 + 2 approach in which one of the two dipyrromethanes bears both of the bridging carbons in the porphyrin products, affording porphyrin 50 which possesses three different aryl rings, with one pair of uniquely opposite identical aryl groups. The last two 2 + 2 methods are further extended to give a tetraarylporphyrin 38 bearing four different aryl groups in a predesignated array, the structure of which is confirmed by a single-crystal X-ray study.