2-(benzoylethynyl)-5-(4-chlorophenyl)-1H-pyrrole

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2-(benzoylethynyl)-5-(4-chlorophenyl)-1H-pyrrole
• 英文别名: 3-[5-(4-chlorophenyl)-1H-pyrrol-2-yl]-1-phenylprop-2-yn-1-one
• 化学式: C₁₉H₁₂ClNO
• 分子量: 305.763
• InChiKey: NYLWXGDABIKYNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(benzoylethynyl)-5-(4-chlorophenyl)-1H-pyrrole 在 copper(l) iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 8.5h， 生成
  参考文献：
  名称：

  Copper(I) halide-promoted formation of 3-acyl-5-halopyridine moiety from NH-2-(2-acylethynyl)pyrroles and propargylamine

  摘要：

  Available NH-2-acylethynylpyrroles undergo annulation/aromatization with propargylamine in the presence of 1 equiv. of CuHal (Hal = Cl, Br, I) at 60-65 degrees C to afford 3-acyl-2-(pyrrol-2-yl)pyridines and their 5-halo analogues in 28-61 and 5-14% yields, respectively. The latter are assumed to be resulted from halohydrogenation of the intermediate Cu-pyrrolylpropargyl amino enones.

  DOI：

  10.1016/j.mencom.2019.05.003
• 作为产物：
  描述：

  2-(4-氯苯基)吡咯 、 3-溴-1-苯基丙-2-炔-1-酮 在 aluminum oxide 作用下， 反应 2.0h， 生成 2-(benzoylethynyl)-5-(4-chlorophenyl)-1H-pyrrole
  参考文献：
  名称：

  Pyrrole–Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles

  摘要：

  一种高效的方法已经开发出来，通过易得的酰基乙炔吡咯与硝酸胍的环缩合反应，合成了具有药用前景的吡咯-氨基嘧啶组合物（收率高达91%）。该反应在KOH/DMSO体系中在加热条件下进行（110-115°C，4小时）。在2-苯甲酰基乙炔吡咯的情况下，观察到形成的吡咯-氨基嘧啶作为N-（吡咯环的NH部分）和C-（氨基嘧啶的CH）亲核试剂意外地加到三键上。

  DOI：

  10.3390/molecules26061692

文献信息

• Facile [2+2] Cycloaddition of DDQ to an Alkyne: Synthesis of Pyrrolyl- and Indolylbicyclo[4.2.0]octadienes from C-Ethynylpyrroles or C-Ethynylindoles
  作者：Boris Trofimov、Lyubov’ Sobenina、Zinaida Stepanova、Igor’ Ushakov、Lidiya Sinegovskaya、Tamara Vakul’skaya、Al’bina Mikhaleva

  DOI：10.1055/s-0029-1217133

  日期：2010.2

  C-Ethynylpyrroles or -indoles, which can be prepared by cross-coupling of pyrroles or indoles with haloalkynes on active surfaces, undergo [2+2]-cycloaddition reactions with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to give 2-pyrrolyl- or 3-indolylbicyclooctadienes in almost quantitative yields. The adducts are charge-transfer complexes that are paramagnetic in the solid state, and therefore represent a new family of densely functionalized pyrrole and indole derivatives potentially useful as pharmaceutical candidates, highly potent building blocks, or precursors of advanced materials. The reaction contributes to the practical and basic chemistry of pyrroles, indoles, alkynes, and quinones.

  C-乙炔基吡咯或吲哚，可通过吡咯或吲哚与卤代炔烃在活性表面上进行交叉耦合制备，与2,3-二氯-5,6-二氰基-1,4-苯醌发生[2+2]环加成反应，以几乎定量的产率生成2-吡咯基或3-吲哚基双环辛二烯。这些加成物是固态下顺磁性的电荷转移复合物，因此代表了一类新型的密集功能化吡咯和吲哚衍生物，可能作为潜在的药物候选者、高效构建模块或高级材料的前体。该反应促进了吡咯、吲哚、炔烃和醌的实用及基础化学研究。
• Pyrrole–Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles
  作者：Olga V. Petrova、Arsalan B. Budaev、Elena F. Sagitova、Igor A. Ushakov、Lyubov N. Sobenina、Andrey V. Ivanov、Boris A. Trofimov

  DOI：10.3390/molecules26061692

  日期：——

  An efficient method for the synthesis of pharmaceutically prospective pyrrole–aminopyrimidine ensembles (in up to 91% yield) by the cyclocondensation of easily available acylethynylpyrroles with guanidine nitrate has been developed. The reaction proceeds under heating (110–115 °C, 4 h) in the KOH/DMSO system. In the case of 2-benzoylethynylpyrrole, the unexpected addition of the formed pyrrole–aminopyrimidine as N- (NH moiety of the pyrrole ring) and C- (CH of aminopyrimidine) nucleophiles to the triple bond is observed.

  一种高效的方法已经开发出来，通过易得的酰基乙炔吡咯与硝酸胍的环缩合反应，合成了具有药用前景的吡咯-氨基嘧啶组合物（收率高达91%）。该反应在KOH/DMSO体系中在加热条件下进行（110-115°C，4小时）。在2-苯甲酰基乙炔吡咯的情况下，观察到形成的吡咯-氨基嘧啶作为N-（吡咯环的NH部分）和C-（氨基嘧啶的CH）亲核试剂意外地加到三键上。
• Chemo- and stereoselective synthesis of E-2-(2-acyl-1-tosylvinyl)pyrroles from tosylmethyl isocyanide (TosMIC) and 2-(acylethynyl)pyrroles
  作者：Ivan V. Saliy、Maxim D. Gotsko、Lyubov' N. Sobenina、Igor A. Ushakov、Boris A. Trofimov

  DOI：10.1016/j.tetlet.2021.153432

  日期：2021.11

  Uniquely functionalized at the double bond with tosyl and acyl substituents, E-2-(2-acyl-1-tosylvinyl)pyrroles, are chemo- and stereoselectively formed in up to 82% yield in reaction (Et3N/MeCN) of tosylmethyl isocyanide (TosMIC) and available 2-(acylethynyl)pyrroles.

  E-2-(2-acyl-1-tosylvinyl)pyrroles 在双键上具有对甲苯磺酰基和酰基取代基的独特功能化，在甲苯磺酰基甲基的反应 (Et 3 N/MeCN)中化学和立体选择性地形成，产率高达 82%异氰化物 (TosMIC) 和可用的 2-（酰基乙炔基）吡咯。
• From Acylethynylpyrroles to Pyrrolo[1,2-a]pyrazines in One Step
  作者：E. F. Sagitova、L. N. Sobenina、B. A. Trofimov

  DOI：10.1134/s1070428020020082

  日期：2020.2

  AbstractAn efficient one-step method for the synthesis of pyrrolo[1,2-a]pyrazines has been developed. The method involves the addition of propargylamine to 2-(acylethynyl)pyrroles followed by a base-catalyzed (Cs2CO3) intramolecular cyclization of the resulting N-propargyl(pyrrolyl)aminoenones.

  摘要已经开发了一种高效的一步合成吡咯并[1,2- a ]吡嗪的方法。该方法包括将炔丙基胺添加到2-（酰基乙炔基）吡咯中，然后对所得的N-炔丙基（吡咯基）氨基烯酮进行碱催化的（Cs 2 CO 3）分子内环化。
• Synthesis of 2-benzoylethynylpyrroles by cross coupling of 2-arylpyrroles with 1-benzoyl-2-bromoacetylene over aluminum oxide
  作者：B. A. Trofimov、L. N. Sobenina、Z. V. Stepanova、A. P. Demenev、A. I. Mikhaleva、I. A. Ushakov、T. I. Vakul’skaya、O. V. Petrova

  DOI：10.1134/s1070428006090168

  日期：2006.9

  Cross coupling of 2-arylpyrrole with benzoylbromoacetylene over aluminum oxide at room temperature gave 45-94% of 2-(benzoylethynyl)-5-arylpyrroles. Intermediate 2-(2-benzoyl-1-bromoethenyl)-5-arylpyrroles were isolated in up to 19% yield. The reaction was accompanied by formation of less than 5% of adducts of the initial pyrroles with the cross-coupling products, 2-benzoyl-1,1-bis(5-arylpyrrol-2-yl)ethenes.