5-chloro-4-formyl-2-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester | 901764-63-4

• 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-chloro-4-formyl-2-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester
• 英文别名: ethyl 2-methyl-5-oxo-4,5-dihydropyrrole-3-carboxylate；ethyl 5-chloro-4-formyl-2-phenyl-1H-pyrrole-3-carboxylate
• CAS: 901764-63-4
• 化学式: C₁₄H₁₂ClNO₃
• 分子量: 277.707
• InChiKey: CAPKFFRFCFRGML-UHFFFAOYSA-N

物化性质

• 熔点：
  160 °C
• 沸点：
  513.1±50.0 °C(Predicted)
• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-4-formyl-2-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester 在 potassium carbonate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 4.0h， 生成 8-benzyl-10-ethoxycarbonyl-9-phenylpyrrolo[7,6-b]-1,4-benzothiazepine
  参考文献：
  名称：

  Synthesis of 5-aryl-2-oxopyrrole derivatives as synthons for highly substituted pyrroles

  摘要：

  A small library of 2-oxo-5-(hetero)arylpyrroles was prepared starting from 2,3-dioxo-5-(hetero)arylpyrrolidines. The large synthetic possibilities of these 2-oxopyrroles were investigated. The 2-oxopyrroles offer a large number of possible derivatizations including reactions with electrophiles. The chloroformylation of 2-oxo-5-(hetero)arylpyrroles provides pyrrole carbaldehydes. Some pyrrole carbaldehydes were used to synthesize polycyclic compounds like pyrrolo[3,4-d]pyridazinones, a thienopyrrole, apyrrolobenz[1,4]oxazepine, a pyrrolobenzo[1,4]thiazepine, and a pyrrolobenzo[1,4]diazepine. Hereby we showed through a short exploration that the oxopyrroles and analogues are interesting and versatile synthetic building blocks. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.005
• 作为产物：
  描述：

  丁二酸,苯甲酰-,二乙基酯 在 乙酸铵 、 溶剂黄146 、 三氯氧磷 作用下， 反应 5.0h， 生成 5-chloro-4-formyl-2-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of 5-aryl-2-oxopyrrole derivatives as synthons for highly substituted pyrroles

  摘要：

  A small library of 2-oxo-5-(hetero)arylpyrroles was prepared starting from 2,3-dioxo-5-(hetero)arylpyrrolidines. The large synthetic possibilities of these 2-oxopyrroles were investigated. The 2-oxopyrroles offer a large number of possible derivatizations including reactions with electrophiles. The chloroformylation of 2-oxo-5-(hetero)arylpyrroles provides pyrrole carbaldehydes. Some pyrrole carbaldehydes were used to synthesize polycyclic compounds like pyrrolo[3,4-d]pyridazinones, a thienopyrrole, apyrrolobenz[1,4]oxazepine, a pyrrolobenzo[1,4]thiazepine, and a pyrrolobenzo[1,4]diazepine. Hereby we showed through a short exploration that the oxopyrroles and analogues are interesting and versatile synthetic building blocks. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.005

文献信息

• Synthesis of thieno[2,3-b]pyrrole-2(4)-carboxylic and 2,4-dicarboxylic acids
  作者：Alina N. Grozav、Mariana Z. Fedoriv、Vitaliy A. Chornous、Alina A. Palamar、Mykhailo K. Bratenko、Mykhailo V. Vovk

  DOI：10.1007/s10593-019-02476-8

  日期：2019.5

  1-Substituted 5-chloro-4-formylpyrrole-3-carboxylates reacted with thioglycolic acid or ethyl thioglycolate in EtOH containing EtONa at room temperature, forming 4-(ethoxycarbonyl)thieno[2,3-b]pyrrole-2-carboxylic acids or thieno[2,3-b]pyrrole-2,4-dicarboxylates. Cyclocondensation with thioglycolic acid upon refluxing in K2CO3–DMF system was accompanied by decarboxylation and led to the formation of

  在室温下，在含有EtONa的EtOH中，将1-取代的5-氯-4-甲酰基吡咯-3-羧酸酯与巯基乙酸或巯基乙醇酸乙酯反应，生成4-（乙氧基羰基）噻吩并[2,3 - b ]吡咯-2-羧酸或噻吩并[2,3 - b ]吡咯-2,4-二羧酸酯。在K 2 CO 3 -DMF系统中回流时，与巯基乙酸进行环缩合会伴随脱羧作用，并导致形成噻吩并[2,3 - b ]吡咯-4-羧酸酯。用LiOH水解获得的羧酸盐，得到噻吩并[2，3 - b ]吡咯-2（4）-羧酸和2，4-二羧酸。
• Cyclocondensation of 5-chloro-4-formylpyrrole-3-carboxylates with arylamines. Synthesis and fluorescent properties of pyrrolo[2,3-b]quinoline-3-carboxylates and their benzo[f] analogs
  作者：Alina N. Grozav、Mariana Z. Fedoriv、Vitaliy А. Chornous、Sergiy V. Kemskiy、Vladislav M. Polishchuk、Nikolay P. Shandura、Eduard B. Rusanov、Mikhailo V. Vovk

  DOI：10.1007/s10593-021-03017-y

  日期：2021.10

  5-Chloro-4-formylpyrrole-3-carboxylates react with anilines or β-naphthylamine when heated in DMF under reflux to form ethyl pyrrolo[2,3-b]quinoline-3-carboxylates or their benzo[f] analogs, which exhibit moderate fluorescent properties. The corresponding carboxylic acids were obtained by alkaline hydrolysis of the synthesized carboxylates.

  5-Chloro-4-formylpyrrole-3-carboxylates 在 DMF 中回流加热时与苯胺或 β-naphthylamine 反应生成吡咯并[2,3 - b ]quinoline-3-carboxylates 或其苯并[ f ]类似物，中等荧光特性。相应的羧酸通过合成的羧酸盐的碱水解获得。