methyl 2-(p-tolyl)-1H-pyrrole-3-carboxylate | 212071-01-7

• 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-(p-tolyl)-1H-pyrrole-3-carboxylate
• 英文别名: 1H-Pyrrole-3-carboxylic acid, 2-(4-methylphenyl)-, methyl ester；methyl 2-(4-methylphenyl)-1H-pyrrole-3-carboxylate
• CAS: 212071-01-7
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: MOHNKMYCRWMAOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  42.09
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-p-Tolyl-1-(2-trimethylsilanyl-ethanesulfonyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid methyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以65%的产率得到methyl 2-(p-tolyl)-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

• IBX-Promoted Oxidative Cyclization of <i>N</i>-Hydroxyalkyl Enamines: A Metal-Free Approach toward 2,3-Disubstituted Pyrroles and Pyridines
  作者：Peng Gao、Huai-Juan Chen、Zi-Jing Bai、Mi-Na Zhao、Desuo Yang、Juan Wang、Ning Wang、Lele Du、Zheng-Hui Guan

  DOI：10.1021/acs.joc.0c00625

  日期：2020.6.19

  An iodoxybenzoic acid-mediated selected oxidative cyclization of N-hydroxyalkyl enamines was developed. Through this strategy, a variety of 2,3-disubstituted pyrroles and pyridines were produced in good selectivity involving oxidation of alcohol, followed by condensation of aldehyde and α-C of enamines. Furthermore, this metal-free method has several advantages, including the use of environmentally

  开发了碘氧基苯甲酸介导的N-羟烷基烯胺的选择氧化环化。通过这种策略，以良好的选择性生产了各种2,3-二取代的吡咯和吡啶，涉及醇的氧化，然后醛与烯胺的α-C缩合。此外，这种无金属方法具有多个优点，包括使用环保试剂，广泛的底物范围，温和的反应条件和高效率。
• 一种2-芳基-3-酯基多取代吡咯类化合物及其 合成精制方法
  申请人：宝鸡文理学院

  公开号：CN109020860B

  公开（公告）日：2021-06-22

  本发明属于化学合成领域，涉及一系列2‑芳基‑3‑酯基多取代吡咯类化合物及其合成精制方法。所述化合物的结构通式如式(Ⅰ)所示，其中R1＝芳基或杂环基，R2＝酯基或氰基。该合成方法以烯胺酯类化合物为原料，通过2‑碘酰基苯甲酸促进氧化环化生成2‑芳基‑3‑酯基多取代吡咯类化合物，操作简单，制备成本较低，相对收率和纯度更高，环境污染少。