2-Furan-2-yl-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid methyl ester | 190272-69-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Furan-2-yl-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid methyl ester
• 英文别名: Methyl 2-(furan-2-yl)-1-(4-methylphenyl)sulfonyl-2,5-dihydropyrrole-3-carboxylate
• CAS: 190272-69-6
• 化学式: C₁₇H₁₇NO₅S
• 分子量: 347.392
• InChiKey: BSGXNTRAOSRSIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  85.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-Furan-2-yl-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid methyl ester 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 以14%的产率得到1-甲苯磺酰基-1H-吡咯-3-羧酸甲酯
  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：

  2,3-丁二烯酸甲酯 、 (E)-N-(furan-2-ylmethylene)-4-methylbenzenesulfonamide 在 三苯基膦 作用下， 以 苯 为溶剂， 以83%的产率得到2-Furan-2-yl-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Phosphine-catalyzed [3+2] cycloaddition reaction of methyl 2,3-butadienoate and N-tosylimines. A novel approach to nitrogen heterocycles

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(97)00656-4

文献信息

• 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.