2,3-di(ethoxycarbonyl)-4-methylpyrrole | 131992-01-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,3-di(ethoxycarbonyl)-4-methylpyrrole
• 英文别名: Diethyl 4-methylpyrrole-2,3-dicarboxylate；diethyl 4-methyl-1H-pyrrole-2,3-dicarboxylate
• CAS: 131992-01-3
• 化学式: C₁₁H₁₅NO₄
• 分子量: 225.244
• InChiKey: VKKJRIMVRGLWHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-di(ethoxycarbonyl)-4-methylpyrrole 、 苯甲酰氯 在 1.) K 作用下， 生成 diethyl 1-benzoyl-4-methylpyrrole-2,3-dicarboxylate
  参考文献：
  名称：

  Monti, Donato; Sleiter, Giancarlo, Gazzetta Chimica Italiana, 1990, vol. 120, # 9, p. 587 - 590

  摘要：

  DOI：
• 作为产物：
  描述：

  diethyl 1-benzoyl-4-methylpyrrole-2,3-dicarboxylate 生成 2,3-di(ethoxycarbonyl)-4-methylpyrrole
  参考文献：
  名称：

  MONTI, DONATO;SLEITER, GIANCARLO, GAZZ. CHIM. ITAL., 120,(1990) N, C. 587-590

  摘要：

  DOI：

文献信息

• Pyrrolotriazine-5-carboxylate ester inhibitors of EGFR and HER2 protein tyrosine kinases and a novel one-pot synthesis of C-4 subsitituted pyrrole-2,3-dicarboxylate diesters
  作者：Harold Mastalerz、Ashvinikumar V Gavai、Brian Fink、Charles Struzynski、James Tarrant、Gregory D Vite、Tai W Wong、Guifen Zhang、Dolatrai M Vyas

  DOI：10.1139/v06-037

  日期：2006.4.1

  2,3-diesters that were made by a new, one-pot procedure. This involved reaction of readily available N-tosyl derivatives of α-amino acid esters or ketones with triphenylphosphine and diethyl acetylenedicarboxylate to form 3-pyrrolines via an intramolecular Wittig olefination. The 3-pyrroline intermediates were not isolated but treated directly with base to eliminate toluenesulfinic acid and generate

  在 C-5 上具有酯基的吡咯并三嗪被制备并评估为 EGFR 和 HER2 受体酪氨酸激酶的抑制剂，这些激酶是癌症治疗的验证靶点。C-5 酯 (15) 至少与其 C-6 酯类似物 (17) 一样有效，这是已知系列吡咯并三嗪 EGRF/HER2 激酶抑制剂的一个例子，显示出良好的生化和细胞活性。C-5 酯是由吡咯 2,3-二酯合成的，该二酯是通过新的一锅法制备的。这涉及容易获得的 α-氨基酸酯或酮的 N-甲苯磺酰基衍生物与三苯基膦和乙炔二羧酸二乙酯的反应，通过分子内 Wittig 烯化反应形成 3-吡咯啉。3-吡咯啉中间体没有被分离，而是直接用碱处理以消除甲苯亚磺酸并以良好的产率生成吡咯2,3-二酯。
• Copper- or Phosphine-Catalyzed Reaction of Alkynes with Isocyanides. Regioselective Synthesis of Substituted Pyrroles Controlled by the Catalyst
  作者：Shin Kamijo、Chikashi Kanazawa、Yoshinori Yamamoto

  DOI：10.1021/ja051875m

  日期：2005.6.1

  The copper-catalyzed reaction of isocyanides (CNCH(2)EWG(1)) 1 with electron-deficient alkynes (RC equivalent to CEWG(2)) 2 gave the 2,4-di-EWG-substituted pyrroles 3 selectively, whereas the phosphine-catalyzed reaction of 1 with 2 afforded the 2,3-di-EWG-subsituted pyrroles 4. Accordingly, regioselective synthesis of substituted pyrroles has been achieved by merely choosing the catalyst.
• Phosphine-catalyzed regioselective heteroaromatization between activated alkynes and isocyanides leading to pyrroles
  作者：Shin Kamijo、Chikashi Kanazawa、Yoshinori Yamamoto

  DOI：10.1016/j.tetlet.2005.02.104

  日期：2005.4

  The organophosphine catalyzed reaction of activated alkynes with isocyanides produces the corresponding heteroaromatization products, pyrroles, regioselectively in good yields. The reaction proceeds most probably through the 1,4-addition of the nucleophilic phosphine catalyst to the alkynes, followed by a [3+2] cycloaddition between the resulting alkenyl phosphine intermediates and a carbanion derived from the isocyanides. (c) 2005 Elsevier Ltd. All rights reserved.
• Fischer; Wiedemann, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1926, vol. 155, p. 61
  作者：Fischer、Wiedemann

  DOI：——

  日期：——