N,N'-dimethyl-N-(prop-2-ynyl)-1H-pyrrole-2-carboxamide

• 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,N'-dimethyl-N-(prop-2-ynyl)-1H-pyrrole-2-carboxamide
• 英文别名: 1-methyl-1H-pyrrole-2-carboxylic acid methylprop-2-ynylamide；N,1-dimethyl-N-(prop-2-yn-1-yl)-1H-pyrrole-2-carboxamide；N,1-dimethyl-N-prop-2-ynylpyrrole-2-carboxamide
• 化学式: C₁₀H₁₂N₂O
• 分子量: 176.218
• InChiKey: GPDGFLUBBBVCJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N'-dimethyl-N-(prop-2-ynyl)-1H-pyrrole-2-carboxamide 、 4-碘代苯乙酮 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以80%的产率得到1-methyl-1H-pyrrole-2-carboxylic acid [3-(4-acetylphenyl)prop-2-ynyl]methylamide
  参考文献：
  名称：

  铂催化炔烃的分子内环化：吡咯并ze庚醌衍生物的高效合成

  摘要：

  实现封闭：铂催化的环异构化反应（参见方案； [Pd / Cu] = [PdCl 2（PPh 3）2 ] / CuI，Ar =芳基，X = Br，I）可用于生物的高效直接合成相关的吡咯并[3,2 – c ] azepin-4-one衍生物。

  DOI：

  10.1002/anie.200902937
• 作为产物：
  描述：

  N-甲基炔丙基胺 、 N-甲基-2-吡咯羧酸 在 4-二甲氨基吡啶 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到N,N'-dimethyl-N-(prop-2-ynyl)-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  铂催化炔烃的分子内环化：吡咯并ze庚醌衍生物的高效合成

  摘要：

  实现封闭：铂催化的环异构化反应（参见方案； [Pd / Cu] = [PdCl 2（PPh 3）2 ] / CuI，Ar =芳基，X = Br，I）可用于生物的高效直接合成相关的吡咯并[3,2 – c ] azepin-4-one衍生物。

  DOI：

  10.1002/anie.200902937

文献信息

• Access to pyrrolo-pyridines by gold-catalyzed hydroarylation of pyrroles tethered to terminal alkynes
  作者：Elena Borsini、Gianluigi Broggini、Andrea Fasana、Chiara Baldassarri、Angelo M Manzo、Alcide D Perboni

  DOI：10.3762/bjoc.7.170

  日期：——

  In a simple procedure, the intramolecular hydroarylation of N-propargyl-pyrrole-2-carboxamides was accomplished with the aid of gold(III) catalysis. The reaction led to differently substituted pyrrolo[2,3-c]pyridine and pyrrolo[3,2-c]pyridine derivatives arising either from direct cyclization or from a formal rearrangement of the carboxamide group. Terminal alkynes are essential to achieve bicyclic

  在一个简单的程序中，N-炔丙基-吡咯-2-甲酰胺的分子内氢化芳基化是在金（III）催化的帮助下完成的。该反应导致不同取代的吡咯并[2,3-c]吡啶和吡咯并[3,2-c]吡啶衍生物由直接环化或羧酰胺基团的正式重排产生。末端炔烃对于通过 6-exo-dig 过程实现双环吡咯并稠合吡啶酮是必不可少的，而 CC 三键上苯基的存在促进了 7-endo-dig 环化，得到了吡咯并氮杂。
• New Pyrrole Inhibitors of Monoamine Oxidase:  Synthesis, Biological Evaluation, and Structural Determinants of MAO-A and MAO-B Selectivity
  作者：Giuseppe La Regina、Romano Silvestri、Marino Artico、Antonio Lavecchia、Ettore Novellino、Olivia Befani、Paola Turini、Enzo Agostinelli

  DOI：10.1021/jm060882y

  日期：2007.3.1

  A series of new pyrrole derivatives have been synthesized and evaluated for their monoamine oxidase (MAO) A and B inhibitory activity and selectivity. N-Methyl,N-(benzyl),N-(pyrrol-2-ylmethyl)amine (7) and N-(2-benzyl),N-(1-methylpyrrol-2-ylmethyl)amine (18) were the most selective MAO-B (7, SI = 0.0057) and MAO-A (18, SI = 12500) inhibitors, respectively. Docking and molecular dynamics simulations gave structural insights into the MAO-A and MAO-B selectivity. Compound 18 forms an H-bond with Gln215 through its protonated amino group into the MAO-A binding site. This H-bond is absent in the 7/MAO-A complex. In contrast, compound 7 places its phenyl ring into an aromatic cage of the MAO-B binding pocket, where it forms charge-transfer interactions. The slightly different binding pose of 18 into the MAO-B active site seems to be forced by a bulkier Tyr residue, which replaces a smaller Ile residue present in MAO-A.
• Diversity-Oriented Approach to Pyrrole-Imidazole Alkaloid Frameworks
  作者：Manojkumar R. Bhandari、Muhammed Yousufuddin、Carl J. Lovely

  DOI：10.1021/ol200067e

  日期：2011.3.18

  An exploration of imidazolylpropargyl amides as linchpin synthons for the construction of a diverse array of heterocyclic frameworks, many of which are related to those found in the oroidin derived alkaloids, is described. One such intermediate has been used in a formal total synthesis of cyclooroidin.
• Platinum-Catalyzed Intramolecular Cyclizations of Alkynes: Efficient Synthesis of Pyrroloazepinone Derivatives
  作者：Marina Gruit、Dirk Michalik、Annegret Tillack、Matthias Beller

  DOI：10.1002/anie.200902937

  日期：2009.9.14

  Achieving closure: A platinum‐catalyzed cycloisomerization reaction (see scheme; [Pd/Cu]=[PdCl2(PPh3)2]/CuI, Ar=aryl, X=Br,I) is used for the efficient straightforward synthesis of biologically relevant pyrrolo‐[3,2‐c]azepin‐4‐one derivatives.

  实现封闭：铂催化的环异构化反应（参见方案； [Pd / Cu] = [PdCl 2（PPh 3）2 ] / CuI，Ar =芳基，X = Br，I）可用于生物的高效直接合成相关的吡咯并[3,2 – c ] azepin-4-one衍生物。
• 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。