2-Benzoyl-5-formylpyrrole | 121643-39-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Benzoyl-5-formylpyrrole
• 英文别名: 5-benzoylpyrrole-2-carboxaldehyde；5-benzoyl-1H-pyrrole-2-carbaldehyde
• CAS: 121643-39-8
• 化学式: C₁₂H₉NO₂
• mdl: MFCD18449454
• 分子量: 199.209
• InChiKey: DQDUAJJNVKIGNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Benzoyl-5-formylpyrrole 在 lithium aluminium tetrahydride 作用下， 以 溶剂黄146 、 丙酸 为溶剂， 生成 N4C20H10(p-CH3C6H4)2Ph2
  参考文献：
  名称：

  Stepwise syntheses of unsymmetrical tetra-arylporphyrins. Adaptation of the macdonald dipyrrole self-condensation methodology

  摘要：

  DOI：

  10.1016/s0040-4039(00)88540-8
• 作为产物：
  描述：

  4-苯甲酰吗啉 在 三氯氧磷 作用下， 反应 27.42h， 生成 2-Benzoyl-5-formylpyrrole
  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

• Lithiated Azafulvenes by Halogen/Metal Interchange of Brominated 6-(Diisopropylamino)-1-azafulvene Derivatives. Novel synthesis of 5-mono- and 4,5-disubstituted 1H-pyrrole-2-carbaldehydes
  作者：Brian L. Bray、Petr Hess、Joseph M. Muchowski、Markus E. Scheller

  DOI：10.1002/hlca.19880710823

  日期：1988.12.14

  The first known lithiated 1-azafulvene derivatives were generated by low-temperature halogen/metal interchange, with t-BuLi, from the corresponding brominated 6-diisopropylamino compounds 3b and 12. These Li species reacted with sundry eletrophilic reagents to give products which, on basic hydrolysis, were converted into 5-mono- or 4,5-disubstituted pyrrole-2-carbaldehydes 10 and 16, respectively.

  通过低温卤素/金属与t -BuLi的交换，从相应的溴化6-二异丙基氨基化合物3b和12生成了第一个已知的锂化1-氮杂富烯衍生物。这些Li物种与各种电子亲和试剂反应，生成的产品经碱性水解后分别转化为5-单-或4,5-二取代的吡咯-2-甲醛10和16。
• Site‐Selective Decarboxylative Direct Formylation of Nitrogen Heterocycles (Azaindoles, Indoles, Pyrroles) and Anilines Utilizing Glyoxylic Acid
  作者：Joydev Laha、Mandeep Kaur Hunjan、Tapas Maity、Amitava Hazra

  DOI：10.1002/adsc.202201384

  日期：——

  A new method for formylation of nitrogen heterocycles overcoming the limitations of classical approaches using a cheap feedstock formylating agent especially under mild and neutral conditions is the subject of this current investigation. This work describes direct formylation of nitrogen heterocycles (azaindoles, indoles, pyrroles) and anilines using glyoxylic acid as the formyl source and K2S2O8 as

  一种新的氮杂环甲酰化方法克服了使用廉价原料甲酰化剂的经典方法的局限性，特别是在温和和中性条件下，这是当前研究的主题。这项工作描述了使用乙醛酸作为甲酰源和 K 2 S 2 O 8对氮杂环化合物（氮杂吲哚、吲哚、吡咯）和苯胺的直接甲酰化作为独家试剂。关键特征包括在中性和温和反应条件下进行 C- 和 N- 甲酰化的通用方法。该方法在含氮杂环化合物、药物和天然产物的串联合成中的应用进一步得到证实。与用芳基乙醛酸进行的芳酰化不同，现在公开了一种以前未知的在 K 2 S 2 O 8存在下用乙醛酸进行直接甲酰化的途径。
• Berthiaume, Sylvie L.; Bray, Brian L.; Hess, Petr, Canadian Journal of Chemistry, 1995, vol. 73, # 5, p. 675 - 684
  作者：Berthiaume, Sylvie L.、Bray, Brian L.、Hess, Petr、Liu, Yanzhou、Maddox, Michael L.、et al.

  DOI：——

  日期：——
• BRAY, BRIAN L.;HESS, PETR;MUCHOWSKI, JOSEPH M.;SCHELLER, MARKUS E., HELV. CHIM. ACTA, 71,(1988) N 8, C. 2053-2057
  作者：BRAY, BRIAN L.、HESS, PETR、MUCHOWSKI, JOSEPH M.、SCHELLER, MARKUS E.

  DOI：——

  日期：——
• 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.