N-propargyl-1-methyl-1H-pyrrole-2-carboxamide | 1033037-35-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-propargyl-1-methyl-1H-pyrrole-2-carboxamide
• 英文别名: 1-methyl-N-(prop-2-yn-1-yl)-1H-pyrrole-2-carboxamide；1-methyl-1H-pyrrole-2-carboxylic acid prop-2-ynylamide；1-methyl-N-prop-2-ynylpyrrole-2-carboxamide
• CAS: 1033037-35-2
• 化学式: C₉H₁₀N₂O
• mdl: MFCD14631524
• 分子量: 162.191
• InChiKey: PVBLDCADIAHOKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  34
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-propargyl-1-methyl-1H-pyrrole-2-carboxamide 在 N-碘代丁二酰亚胺 、 copper dichloride 作用下， 以 乙腈 为溶剂， 以52%的产率得到(E)-5-(iodomethylidene)-2-(methylpyrrol-2-yl)-4,5-dihydrooxazole
  参考文献：
  名称：

  Copper(II)-Catalyzed Alkoxyhalogenation of Alkynyl Ureas and Amides as a Route to Haloalkylidene-Substituted Heterocycles

  摘要：

  A highly effective synthesis of haloalkylidene-substituted heterocycles by copper(II)-catalyzed cyclization of alkynyl ureas and secondary amides has been developed. The reaction, which involves a catalytic amount of CuCl2 and a stoichiometric amount of N-halosuccinimide, occurs selectively through an alkoxyhalogenation process. Alternatively, alkoxychlorination and alkoxybromination reactions can be performed working solely with stoichiometric CuCl, and CuBr2, respectively.

  DOI：

  10.1021/acs.joc.5b01227
• 作为产物：
  描述：

  1-甲基吡咯-2-羰酰氯 、 炔丙胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以70%的产率得到N-propargyl-1-methyl-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Intramolecular Pd(II)-Catalyzed Cyclization of Propargylamides: Straightforward Synthesis of 5-Oxazolecarbaldehydes

  摘要：

  Direct synthesis of 2-substituted 5-oxazolecarbaldehydes was performed by intramolecular reaction of propargylamides through treatment with a catalytic amount of Pd(II) salts in the presence of a stoichiometric amount of reoxidant agent. The heterocyclization process was well-tolerated by a wide range of aryl, heteroaryl, and alkyl propargylamides. This protocol constitutes a valuable synthetic pathway to 5-oxazolecarbaldehydes, alternative to the formylation on oxazole rings, often unsatisfactory in term of regioselectivity and yields.

  DOI：

  10.1021/jo800621n

文献信息

• Synthesis of pyrroloazepinones: platinum- and gold-catalyzed cyclization reactions of alkynes
  作者：Marina Gruit、Dirk Michalik、Karolin Krüger、Anke Spannenberg、Annegret Tillack、Anahit Pews-Davtyan、Matthias Beller

  DOI：10.1016/j.tet.2010.02.091

  日期：2010.5

  The synthesis of potentially bioactive pyrroloazepinones based on the catalytic intramolecular cyclization of alkyne-substituted 1H-pyrrole-2-carboxylic acid amides has been developed. In the presence of either H2PtCl6·6H2O at 120 °C or AuCl3 at room temperature pyrrolo[3,2-c]azepin-4-ones are formed.

  已经开发了基于炔烃取代的1 H-吡咯-2-羧酸酰胺的催化分子内环化反应的潜在生物活性吡咯并ze庚酮的合成方法。在120°C下存在H 2 PtCl 6 ·6H 2 O或在室温下存在AuCl 3的情况下，会生成吡咯并[3,2 - c ] azepin-4-ones。
• Stereoselective Synthesis of Highly Substituted Conjugated Dienes via Pd‐Catalyzed Carbonylation of 1,3‐Diynes
  作者：Jiawang Liu、Ji Yang、Wolfgang Baumann、Ralf Jackstell、Matthias Beller

  DOI：10.1002/anie.201903533

  日期：2019.7.29

  stereoselective synthesis of conjugated dienes was realized for the first time via Pd‐catalyzed alkoxycarbonylation of easily available 1,3‐diynes. Key to success is the utilization of the specific ligand 1,1′‐ferrocenediyl‐bis(tert‐butyl(pyridin‐2‐yl)phosphine) (L1), which allows this novel transformation to proceed at room temperature. A range of 1,2,3,4‐tetrasubstituted conjugated dienes are obtained in

  共轭二烯的立体选择性合成是通过Pd催化的容易获得的1,3-二炔的烷氧基羰基化首次实现的。成功的关键是利用特定的配体1,1'-二茂铁基-双（叔丁基（吡啶-2-基）膦）（L1），该新颖的转化反应可在室温下进行。通过这种简单的方法，可以以高收率和选择性获得一系列1,2,3,4-四取代的共轭二烯。该协议的综合用途在构成天然产物rac-Cagayanin，rac-galbulin，rac-agastinol和大麻素G的几种重要中间体的简明合成中得到了展示。
• Efficient and simple zinc-mediated synthesis of 3-amidoindoles
  作者：Anahit Pews-Davtyan、Matthias Beller

  DOI：10.1039/c1ob05576c

  日期：——

  A general synthesis of 3-amidoindoles from easily available arylhydrazines and acylated propargylamines is described. In the presence of inexpensive Zn salts, alkyne amination and subsequent Fischer indole-cyclization took place in good yields with excellent regioselectivity providing an interesting scaffold for potentially bio-active compounds.

  本文介绍了一种从易得的芳基肼和酰化的炔丙基胺出发，合成3-酰胺基吲哚的通用方法。在廉价的锌盐存在下，实现了炔烃的胺化和随后的费歇尔吲哚环化反应，产率高且区域选择性优异，为潜在的生物活性化合物提供了一个有趣的骨架。
• 10.1002/anie.202401557
  作者：Bao, Ming、Zhou, Yi、Yuan, Haoxuan、Dong, Guizhi、Li, Chao、Xie, Xiongda、Chen, Kewei、Hong, Kemiao、Yu, Zhi-Xiang、Xu, Xinfang

  DOI：10.1002/anie.202401557

  日期：——

  An enantioselective (4+2) annulation of N-propargylamides and α,β-unsaturated imines/ketones has been accomplished under gold-complex and chiral quinine-derived squaramide synergetic catalysis, providing chiral tetrahydropyridines/dihydropyrans with high efficiency and selectivity. This method complements the (4+2) annulation of allene reagents via a formal cycloaddition on internal π-bond, which is

  在金配合物和手性奎宁衍生的方酰胺协同催化下，完成了N-炔丙基酰胺和α,β-不饱和亚胺/酮的对映选择性(4+2)环化，提供了高效、选择性的手性四氢吡啶/二氢吡喃。该方法通过内部 π-键上的正式环加成补充了丙二烯试剂的 (4+2) 环化，这具有挑战性并且仍然难以捉摸。
• Intramolecular Pd(II)-Catalyzed Cyclization of Propargylamides: Straightforward Synthesis of 5-Oxazolecarbaldehydes
  作者：Egle M. Beccalli、Elena Borsini、Gianluigi Broggini、Giovanni Palmisano、Silvia Sottocornola

  DOI：10.1021/jo800621n

  日期：2008.6.1

  Direct synthesis of 2-substituted 5-oxazolecarbaldehydes was performed by intramolecular reaction of propargylamides through treatment with a catalytic amount of Pd(II) salts in the presence of a stoichiometric amount of reoxidant agent. The heterocyclization process was well-tolerated by a wide range of aryl, heteroaryl, and alkyl propargylamides. This protocol constitutes a valuable synthetic pathway to 5-oxazolecarbaldehydes, alternative to the formylation on oxazole rings, often unsatisfactory in term of regioselectivity and yields.