methyl 4-(2-hydroxybenzoyl)-1H-pyrrole-2-carboxylate | 62484-63-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-(2-hydroxybenzoyl)-1H-pyrrole-2-carboxylate
• 英文别名: methyl 4-(2-hydroxybenzoyl)pyrrole-2-carboxylate；4-(2-hydroxy-benzoyl)-pyrrole-2-carboxylic acid methyl ester；2-Methoxycarbonyl-4-(2-hydroxybenzoyl)-pyrrol
• CAS: 62484-63-3
• 化学式: C₁₃H₁₁NO₄
• 分子量: 245.235
• InChiKey: CMKGUGBEYHVDII-UHFFFAOYSA-N

物化性质

• 熔点：
  149 °C(Solv: ethanol (64-17-5))
• 沸点：
  441.7±35.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  79.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-(2-hydroxybenzoyl)-1H-pyrrole-2-carboxylate 在 copper(l) iodide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以23%的产率得到methyl 4-oxo-1,4-dihydrochromeno[2,3-b]pyrrole-2-carboxylate
  参考文献：
  名称：

  Synthesis of Chromeno[2,3-d]imidazol-9(1H)-ones via Tandem Reactions of 3-Iodochromones with Amidines Involving Copper-Catalyzed C–H Functionalization and C–O Bond Formation

  摘要：

  A novel six-membered heterocyclic skeleton of imidazochromone was prepared via an efficient one-pot reaction including a key step of copper-catalyzed aerobic C-H intramolecular cycloetherification. Notably, this process does not require the presence of strong para electron-withdrawing groups on the phenol component. Also, the results of this effort show that acyl phenols containing electron-rich heterocycles participate in an efficient C-H activation/C-O formation process.

  DOI：

  10.1021/ol401966y
• 作为产物：
  描述：

  4,5-Dihydro-4-<(4-oxo-4H-1-benzopyran-3-yl)methylene>-2-phenyloxazol-5-one 在 二乙胺 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以45%的产率得到methyl 4-(2-hydroxybenzoyl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Ghosh, Chandra Kanta; Bandyopadhyay, Chandrakanta, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 11, p. 1048 - 1053

  摘要：

  DOI：

文献信息

• Synthesis of substituted pyrroles using a silver-catalysed reaction between isocyanoacetates/benzyl isocyanides and chromones
  作者：Xueyu Qi、Haoyue Xiang、Yuhong Yang、Chunhao Yang

  DOI：10.1039/c5ra21915a

  日期：——

  A novel synthetic strategy to construct substituted-pyrroles has been developed through silver-catalysed cycloadditions of isocyanides with chromones.

  已经开发出一种新的合成策略，通过银催化的异氰酸酯与色酮的环加成反应来构建取代吡咯。
• Three-component reactions of isocyanoacetates, amines and 3-formylchromones initiated by an unexpected aza-Michael addition
  作者：Jia-Yu Liao、Wei Jie Yap、Ji'En Wu、Ming Wah Wong、Yu Zhao

  DOI：10.1039/c7cc03468g

  日期：——

  mode of three-component reaction between isocyanoacetates, amines and 3-formylchromones. Both experimental studies and DFT calculations revealed that this Ag-catalyzed unusual transformation is initiated by a facile aza-Michael addition instead of the conventional imine condensation. By using an operationally simple procedure, this catalytic method enables an efficient synthesis of polysubstituted pyrroles

  我们在本文中提出了异氰基乙酸酯，胺和3-甲酰基色酮之间的三组分反应的新模式。实验研究和DFT计算都表明，这种Ag催化的异常转变是由一种简便的aza-Michael加成反应而不是传统的亚胺缩合反应引发的。通过使用操作简单的程序，该催化方法能够从市售起始原料有效合成多取代的吡咯。
• Reaction of chromone-3-carbaldehyde with α-amino acids—syntheses of 3- and 4-(2-hydroxybenzoyl)pyrroles
  作者：Andrea G.P.R. Figueiredo、Augusto C. Tomé、Artur M.S. Silva、José A.S. Cavaleiro

  DOI：10.1016/j.tet.2006.11.034

  日期：2007.1

  Azomethine ylides generated from the reaction of chromone-3-carbaldehyde with α-amino acids undergo 1,5-electrocyclization reactions to afford 3- and 4-(2-hydroxybenzoyl)pyrroles. These ylides can be trapped with dipolarophiles in 1,3-dipolar cycloaddition reactions to yield chromonyl pyrrolidines. The reaction of chromone-3-carbaldehyde with methyl glycinate gives a mixture of pyrrole, pyridine, and 3-aza-9-xanthenone

  由色酮-3-甲醛与α-氨基酸反应生成的甲亚胺基化物经过1，5-电环化反应，得到3-和4-（2-羟基苯甲酰基）吡咯。这些酰基化物可以在1，3-偶极环加成反应中被双极性亲和剂捕获，以产生苯甲酰基吡咯烷。色酮-3-甲醛与甘氨酸甲酯的反应得到吡咯，吡啶和3-氮杂-9-黄酮酮衍生物的混合物。
• Metal-Free Catalyzed Oxidation/Decarboxylative [3+2] Cycloaddition Sequences of 3-Formylchromones to Access Pyrroles with Anti-Cancer Activity
  作者：Xue Li、Xing-Yu Chen、Bing-Ying Fan、Qun Yu、Jie Lei、Zhi-Gang Xu、Zhong-Zhu Chen

  DOI：10.3390/molecules28227602

  日期：——

  An efficient and direct approach to pyrroles was successfully developed by employing 3-formylchromones as decarboxylative coupling partners, and facilitated by microwave irradiation. The protocol utilizes easily accessible feedstocks, a catalytic amount of DBU without any metals, resulting in high efficiency and regioselectivity. Notably, all synthesized products were evaluated against five different cancer cell lines and compound 3l selectively inhibited the proliferation of HCT116 cells with an IC50 value of 10.65 μM.

  通过使用 3-甲酰基色酮作为脱羧偶联剂，并在微波辐照的帮助下，成功开发出了一种高效、直接的吡咯方法。该方法利用容易获得的原料和催化量的 DBU，不含任何金属，因而具有高效率和区域选择性。值得注意的是，所有合成产物都针对五种不同的癌细胞系进行了评估，化合物 3l 选择性地抑制了 HCT116 细胞的增殖，IC50 值为 10.65 μM。
• FITTON A. O.; FROST J. R.; SUSCHITZKY H.; HOUGHTON P. G., SYNTHESIS <SYNT-BF>, 1977, NO 2, 133-135
  作者：FITTON A. O.、 FROST J. R.、 SUSCHITZKY H.、 HOUGHTON P. G.

  DOI：——

  日期：——