2-(thiophen-3-yl)-1H-pyrrole-3-carbonitrile | 1158196-79-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-(thiophen-3-yl)-1H-pyrrole-3-carbonitrile
• 英文别名: 2-thiophen-3-yl-1H-pyrrole-3-carbonitrile
• CAS: 1158196-79-2
• 化学式: C₉H₆N₂S
• 分子量: 174.226
• InChiKey: NQOILLZGXDNPLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-噻吩甲酸甲酯 在 ammonium acetate 、 sodium hydride 、 溶剂黄146 作用下， 以 乙二醇二甲醚 、 mineral oil 为溶剂， 反应 30.0h， 生成 2-(thiophen-3-yl)-1H-pyrrole-3-carbonitrile
  参考文献：
  名称：

  2-取代的 3-氰基吡咯的途径：丹那代尔和 Suffrutine A 的合成

  摘要：

  标题化合物是由 4,4-二甲氧基丁腈和各自的酯通过克莱森缩合和随后的 Paal-Knorr 吡咯合成以两步顺序制备的。该序列可以作为一锅程序进行，在两个步骤中以 47-72% 的产率提供吡咯（13 个例子）。该方法的分子内变体被应用于从各自的三苯甲基保护的ω-氨基链烷酸酯全合成丹那达和suffrutine A。

  DOI：

  10.1021/acs.joc.6b01298

文献信息

• One-Pot Synthesis of 3-Substituted 2-Arylpyrrole in Aqueous Media via Addition–Annulation of Arylboronic Acid and Substituted Aliphatic Nitriles
  作者：Md Yousuf、Susanta Adhikari

  DOI：10.1021/acs.orglett.7b00490

  日期：2017.5.5

  Pd(II)-catalyzed C–C coupling reactions between substituted aliphatic nitriles and arylboronic acids followed by in situ cyclodehydration have been employed for the first time to synthesize a wide variety of 3-substituted 2-aryl-1H-pyrroles in aqueous acetic acid. This one-pot synthesis is green, and it conforms to atom economy. The structures of two representative pyrroles, 3k and 5f, were confirmed

  钯（II）催化的取代脂肪族腈与芳基硼酸之间的CC偶联反应，然后进行原位环脱水，首次用于在乙酸水溶液中合成各种3-取代的2-芳基-1 H-吡咯酸。这种一锅合成法是绿色的，符合原子经济性。X射线晶体学分析证实了两种代表性的吡咯3k和5f的结构。
• Formation of new 4-isocyanobut-2-enenitriles by thermal ring cleavage of 3-pyridyl azides
  作者：Vegar Stockmann、Jan M. Bakke、Per Bruheim、Anne Fiksdahl

  DOI：10.1016/j.tet.2009.02.072

  日期：2009.5

  A new thermal ring cleavage of 3-pyridyl nitrenes for the formation of 4-isocyanobut-2-enenitrile products is reported. Thermolysis of 4-(thien-3-yl)-3-pyridyl azide 1 and 3-azido-4-(1-TIPS-1H-pyrrol-3-yl)pyridine 5 afforded two new isonitrile-nitrile products by ring cleavage; 4-isocyano-2-(thiophen-3-yl)but-2-enenitrile (3, 27%) and 4-isocyano-2-(1-TIPS-1H-pyrrol-3-yl)but-2-enenitrile (7, 20%), in addition to our previously reported pyrido[3,4-b]thienopyrrole (2, 29%) and pyrido[3,4-b]pyrrolo[3,2-d]pyrrole (6, 71%) products. Minor amounts of 2-(thien-3-yl)-1H-pyrrole-3-carbonitrile (4, 6%), formed by ring contraction, were also isolated after thermolysis of azide 1. Isonitriles 3 and 7 underwent degradation into amine 3b and formamide 7a by acidic hydrolysis. The nature and chemistry of compounds 3, 4 and 7 were investigated. (C) 2009 Elsevier Ltd. All rights reserved.