methyl 2-(2-methoxyphenyl)-1H-pyrrole-3-carboxylate | 190273-04-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 2-(2-methoxyphenyl)-1H-pyrrole-3-carboxylate
• CAS: 190273-04-2
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: JERFXNZIJLFMJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  420.6±35.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(2-methoxyphenyl)-1H-pyrrole-3-carboxylate 在 喹啉 、 sodium sulfide 、 氢氧化钾 、 铜 作用下， 以 甲醇 为溶剂， 反应 10.5h， 生成 2-(2-hydroxyphenyl)-1H-pyrrole
  参考文献：
  名称：

  A Novel [3+2] Cycloaddition Approach to Nitrogen Heterocycles via Phosphine-Catalyzed Reactions of 2,3-Butadienoates or 2-Butynoates and Dimethyl Acetylenedicarboxylate with Imines:  A Convenient Synthesis of Pentabromopseudilin

  摘要：

  The reactivity of a new three carbon synthon, generated in situ from the reaction of 2,3-butadienoates or 2-butynoates with an appropriate phosphine as the catalyst, toward the electron deficient imines is described. Triphenylphosphine-catalyzed reaction of-methyl a,3-butadienoate with N-sulfonylimines gave the single [3+2] cycloadduct in excellent yield; tributylphosphine-catalyzed reaction of methyl 2,3-butadienoate or 2-butynoate with N-tosylimines afforded the corresponding [3+2] cycloadduct as the major product along with a small amount of the three components adduct. Aliphatic N-tosylimines gave moderate yield for this reaction. In addition, a new phosphine-catalyzed cyclization reaction of dimethyl acetylenedicarboxylate with N-tosylimines is also described. A:reaction mechanism is proposed. Further elaborations of the cycloaddition products and the synthesis of pentabromopseudilin using this method are exemplified.

  DOI：

  10.1021/jo9723063
• 作为产物：
  描述：

  2-丁炔酸甲酯 在 三丁基膦 、 sodium methylate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 苯 为溶剂， 反应 60.0h， 生成 methyl 2-(2-methoxyphenyl)-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  A Novel [3+2] Cycloaddition Approach to Nitrogen Heterocycles via Phosphine-Catalyzed Reactions of 2,3-Butadienoates or 2-Butynoates and Dimethyl Acetylenedicarboxylate with Imines:  A Convenient Synthesis of Pentabromopseudilin

  摘要：

  The reactivity of a new three carbon synthon, generated in situ from the reaction of 2,3-butadienoates or 2-butynoates with an appropriate phosphine as the catalyst, toward the electron deficient imines is described. Triphenylphosphine-catalyzed reaction of-methyl a,3-butadienoate with N-sulfonylimines gave the single [3+2] cycloadduct in excellent yield; tributylphosphine-catalyzed reaction of methyl 2,3-butadienoate or 2-butynoate with N-tosylimines afforded the corresponding [3+2] cycloadduct as the major product along with a small amount of the three components adduct. Aliphatic N-tosylimines gave moderate yield for this reaction. In addition, a new phosphine-catalyzed cyclization reaction of dimethyl acetylenedicarboxylate with N-tosylimines is also described. A:reaction mechanism is proposed. Further elaborations of the cycloaddition products and the synthesis of pentabromopseudilin using this method are exemplified.

  DOI：

  10.1021/jo9723063

文献信息

• Application of the ring-closing metathesis to the formation of 2-aryl-1H-pyrrole-3-carboxylates as building blocks for biologically active compounds
  作者：Katarzyna Grychowska、Bartłomiej Kubica、Marcin Drop、Evelina Colacino、Xavier Bantreil、Maciej Pawłowski、Jean Martinez、Gilles Subra、Paweł Zajdel、Frédéric Lamaty

  DOI：10.1016/j.tet.2016.09.059

  日期：2016.11

  kinetics on the RCM. After an aromatization step, this methodology allowed for an efficient generation of variously substituted and unprecedented 2-aryl-1H-pyrrole-3-carboxylates in good yields and cost-effectiveness. The resulting molecules might serve as key building blocks for the generation of CNS-oriented compound libraries.

  闭环复分解（RCM）是制备环状有机化合物的有力工具。然而，该方法的主要限制之一是难以制备大量靶分子。在本文中，我们描述了基于相应β-氨基酯的闭环复分解过程作为关键步骤的关于2芳基1 H-吡咯-3-羧酸的克级合成的综合研究。这项研究包括在RCM上评估溶剂和催化剂以及反应动力学。进行芳构化步骤后，此方法可有效生成各种取代的和前所未有的2-芳基-1 H-吡咯-3-羧酸酯具有良好的产率和成本效益。所得的分子可以作为生成面向CNS的化合物库的关键构件。
• Phosphine-catalyzed [3+2] cycloaddition reaction of methyl 2,3-butadienoate and N-tosylimines. A novel approach to nitrogen heterocycles
  作者：Zhenrong Xu、Xiyan Lu

  DOI：10.1016/s0040-4039(97)00656-4

  日期：1997.5

  In the presence of a catalytic amount of triphenylphosphine, methyl 2,3-butadienoate smoothly reacted with aromatic or heteroaromatic N-tosylimines at room temperature to afford the [3+2] cycloaddition product in excellent yield. (C) 1997 Elsevier Science Ltd.
• A Novel [3+2] Cycloaddition Approach to Nitrogen Heterocycles via Phosphine-Catalyzed Reactions of 2,3-Butadienoates or 2-Butynoates and Dimethyl Acetylenedicarboxylate with Imines:  A Convenient Synthesis of Pentabromopseudilin
  作者：Zhenrong Xu、Xiyan Lu

  DOI：10.1021/jo9723063

  日期：1998.7.1

  The reactivity of a new three carbon synthon, generated in situ from the reaction of 2,3-butadienoates or 2-butynoates with an appropriate phosphine as the catalyst, toward the electron deficient imines is described. Triphenylphosphine-catalyzed reaction of-methyl a,3-butadienoate with N-sulfonylimines gave the single [3+2] cycloadduct in excellent yield; tributylphosphine-catalyzed reaction of methyl 2,3-butadienoate or 2-butynoate with N-tosylimines afforded the corresponding [3+2] cycloadduct as the major product along with a small amount of the three components adduct. Aliphatic N-tosylimines gave moderate yield for this reaction. In addition, a new phosphine-catalyzed cyclization reaction of dimethyl acetylenedicarboxylate with N-tosylimines is also described. A:reaction mechanism is proposed. Further elaborations of the cycloaddition products and the synthesis of pentabromopseudilin using this method are exemplified.