dimethyl 2,3-dimethyl-N-hydroxypyrolle-4,5-dicarboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: dimethyl 2,3-dimethyl-N-hydroxypyrolle-4,5-dicarboxylate
• 英文别名: Dimethyl 1-hydroxy-4,5-dimethylpyrrole-2,3-dicarboxylate
• 化学式: C₁₀H₁₃NO₅
• 分子量: 227.217
• InChiKey: JZRIWVKQTGWRFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  二乙酰一肟 、 丁炔二酸二甲酯 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到dimethyl 2,3-dimethyl-N-hydroxypyrolle-4,5-dicarboxylate
  参考文献：
  名称：

  Synthesis of Densely FunctionalizedN-Hydroxypyrroles Mediated by Vinyltriphenylphosphonium Salt

  摘要：

  Protonation of the reactive 1:1 intermediates produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxlates by butane-2,3-dione monoxime leads to vinyltriphenylphosphonium salts, which undergo intramolecular Wittig reaction to produce dialkyl 2,3-dimethyl-N-hydroxypyrrole-4,5-dicarboxylates in fairly high yields.

  DOI：

  10.1080/00397919608003851

文献信息

• Synthesis of Dimethyl 2-(2,4,6-Trimethylphenoxy)-3-triphenylphosphoniobutanedioate and its Application in Intramolecular Wittig Reactions
  作者：Issa Yavari、Farahnaz Nourmohammadian、Hamid R. Bijanzadeh

  DOI：10.1080/10426500211709

  日期：2002.5.1

  Protonation of the reactive 1:1 intermediate produced in the reaction between triphenylphosphine and dimethyl acetylenedicarboxylate by 2,4,6-trimethylphenol leads to a stable ylide in high yield, which is employed in intramolecular Wittig reactions.

  2,4,6-三甲基苯酚对三苯基膦和乙炔二甲酸二甲酯反应中产生的反应性 1:1 中间体进行质子化，以高产率得到稳定的叶立德，可用于分子内 Wittig 反应。
• Synthesis of Densely Functionalized<i>N</i>-Hydroxypyrroles Mediated by Vinyltriphenylphosphonium Salt
  作者：Issa Yavari、Ali Ramazani、Asieh Yahya-Zadeh

  DOI：10.1080/00397919608003851

  日期：1996.12

  Protonation of the reactive 1:1 intermediates produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxlates by butane-2,3-dione monoxime leads to vinyltriphenylphosphonium salts, which undergo intramolecular Wittig reaction to produce dialkyl 2,3-dimethyl-N-hydroxypyrrole-4,5-dicarboxylates in fairly high yields.