1-(4'-methylphenyl)-2-acetylpyrrole | 741717-67-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(4'-methylphenyl)-2-acetylpyrrole
• 英文别名: 1-[1-(4-Methylphenyl)-1H-pyrrol-2-yl]ethanone；1-[1-(4-methylphenyl)pyrrol-2-yl]ethanone
• CAS: 741717-67-9
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: AXCMOQKMFMZNPD-UHFFFAOYSA-N

物化性质

• 沸点：
  325.9±25.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4'-methylphenyl)-2-acetylpyrrole 在 iron(III)-acetylacetonate 、 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 2.0h， 生成 4,7-dimethylpyrrolo[1,2-a]quinoxaline
  参考文献：
  名称：

  Iron-Catalyzed Intramolecular C(sp²)–N Cyclization of 1-(N-Arylpyrrol-2-yl)ethanone O-Acetyl Oximes toward Pyrrolo[1,2-a]quinoxaline Derivatives

  摘要：

  An efficient and convenient iron-catalyzed protocol has been developed for the synthesis of substituted pyrrolo[1,2-a]quinoxalines from 1-(N-arylpyrrol-2-yl)ethanone O-acetyl oximes through N-O bond cleavage and intramolecular directed C-H arylation reactions in acetic acid.

  DOI：

  10.1021/acs.joc.5b00915
• 作为产物：
  描述：

  2-乙酰基吡咯 、 4-甲苯硼酸 在 nickel(II) oxide 、 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以85%的产率得到1-(4'-methylphenyl)-2-acetylpyrrole
  参考文献：
  名称：

  Exploration of Catalytic Activity of Quercetin Mediated Hydrothermally Synthesized NiO Nanoparticles Towards C–N Coupling of Nitrogen Heterocycles

  摘要：

  A new approach towards the preparation of phase pure NiO nanoparticles via quercetin mediated hydrothermal method is proposed in this work. The performance of quercetin as capping agent is found to be good. The XRD and SEM results confirm that the NiO nanoparticles prepared with quercetin are smaller in size and have refined morphology than that prepared without quercetin. Thermal stability, elemental composition and particle size of prepared nanoparticles have been revealed by TG-DSC, EDAX and HR-TEM analysis respectively. N-2 adsorption-desorption isotherm (BET) analysis was done to reveal specific surface area. The prepared NiO nanoparticles act as cost effective, environmental friendly and efficient catalyst for the C-N cross coupling of indole and electron deficient pyrrole, under very mild reaction conditions. The catalytic system is able to tolerate many functional groups with different electronic and structural properties. Hence the present catalytic system may be possibly applied in large scale synthesis. Graphic

  DOI：

  10.1007/s10562-019-03037-6

文献信息

• Copper−Diamine-Catalyzed <i>N</i>-Arylation of Pyrroles, Pyrazoles, Indazoles, Imidazoles, and Triazoles
  作者：Jon C. Antilla、Jeremy M. Baskin、Timothy E. Barder、Stephen L. Buchwald

  DOI：10.1021/jo049658b

  日期：2004.8.1

  This paper details the copper-catalyzed N-arylation of π-excessive nitrogen heterocycles. The coupling of either aryl iodides or aryl bromides with common nitrogen heterocycles (pyrroles, pyrazoles, indazoles, imidazoles, and triazoles) was successfully performed in good yield with catalysts derived from diamine ligands and CuI. General conditions were found that tolerate functional groups such as

  本文详细介绍了铜催化的π-过量氮杂环的N-芳基化反应。芳基碘化物或芳基溴化物与常见的氮杂环（吡咯，吡唑，吲唑，咪唑和三唑）的偶联成功地用衍生自二胺配体和CuI的催化剂进行了高收率的偶联。发现一般条件可耐受芳基卤化物或杂环上的官能团，例如醛，酮，醇，伯胺和腈。使用本文报道的条件，受阻的芳基卤化物或杂环也被发现是合适的底物。
• Iron-Catalyzed Intramolecular C(<i>sp</i>²)–N Cyclization of 1-(<i>N</i>-Arylpyrrol-2-yl)ethanone <i>O</i>-Acetyl Oximes toward Pyrrolo[1,2-<i>a</i>]quinoxaline Derivatives
  作者：Zhiguo Zhang、Junlong Li、Guisheng Zhang、Nana Ma、Qingfeng Liu、Tongxin Liu

  DOI：10.1021/acs.joc.5b00915

  日期：2015.7.2

  An efficient and convenient iron-catalyzed protocol has been developed for the synthesis of substituted pyrrolo[1,2-a]quinoxalines from 1-(N-arylpyrrol-2-yl)ethanone O-acetyl oximes through N-O bond cleavage and intramolecular directed C-H arylation reactions in acetic acid.
• Exploration of Catalytic Activity of Quercetin Mediated Hydrothermally Synthesized NiO Nanoparticles Towards C–N Coupling of Nitrogen Heterocycles
  作者：T. Krishnaveni、K. Lakshmi、K. Kadirvelu、M. V. Kaveri

  DOI：10.1007/s10562-019-03037-6

  日期：2020.6

  A new approach towards the preparation of phase pure NiO nanoparticles via quercetin mediated hydrothermal method is proposed in this work. The performance of quercetin as capping agent is found to be good. The XRD and SEM results confirm that the NiO nanoparticles prepared with quercetin are smaller in size and have refined morphology than that prepared without quercetin. Thermal stability, elemental composition and particle size of prepared nanoparticles have been revealed by TG-DSC, EDAX and HR-TEM analysis respectively. N-2 adsorption-desorption isotherm (BET) analysis was done to reveal specific surface area. The prepared NiO nanoparticles act as cost effective, environmental friendly and efficient catalyst for the C-N cross coupling of indole and electron deficient pyrrole, under very mild reaction conditions. The catalytic system is able to tolerate many functional groups with different electronic and structural properties. Hence the present catalytic system may be possibly applied in large scale synthesis. Graphic