3-(2-nitro-1-phenylethyl)-1H-pyrrole | 1173111-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-(2-nitro-1-phenylethyl)-1H-pyrrole
• CAS: 1173111-08-4
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: JAHLSUAWRGQTQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯甲醛 在 对甲苯磺酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 3-(2-nitro-1-phenylethyl)-1H-pyrrole
  参考文献：
  名称：

  由磺酰吡咯合成3-（2-硝基烷基）吡咯及其转化为6-氮杂吲哚衍生物

  摘要：

  AbstractThe reaction of sulfonylpyrroles with nitroalkanes in the presence of KF/alumina generates 3‐(2‐nitroalkyl)pyrroles in good yields. These compounds can be converted into trisubstituted 6‐azaindoles by a sequence of reactions comprising reduction of the nitro group, Pictet–Spengler cyclization and final oxidative aromatization.magnified image

  DOI：

  10.1002/adsc.201300701

文献信息

• Highly Active La(III)‐Based Metal‐Organic Framework as a Heterogeneous Lewis Acid Catalyst for Friedel‐Crafts Alkylation
  作者：Jia‐Qi Wu、Xin‐Yuan Wu、Jian‐Mei Lu、Qian Shi、Li‐Xiong Shao

  DOI：10.1002/chem.202202441

  日期：2022.12.9

  was successfully synthesized from LaCl3 and 1,1′ : 4′,1′ ′: 4′′,1′′′ : 4′′′,1′′′′-quinquephenyl]-2,2′′,2′′′′,5′′-tetracarboxylic acid (H4qptca) by conventional solvothermal method. Initial studies showed that it was an efficient heterogeneous catalyst for the Friedel-Crafts alkylation of indole and pyrrole with β-nitrostyrene with a wide substrate scope.

  一种新型基于 La(III) 的二维 (2D) 金属有机骨架 [La 2/3 (qptca) 1/2 ] 成功地由 LaCl 3和 1,1' : 4',1' 合成： 4'',1''' : 4''',1''''-quinquephenyl]-2,2'',2'''',5''-四羧酸 (H 4 qptca) 常规溶剂热法. 初步研究表明，它是一种高效的多相催化剂，适用于吲哚和吡咯与 β-硝基苯乙烯的 Friedel-Crafts 烷基化反应，具有广泛的底物范围。
• Simple and Efficient<i>Friedel-Crafts</i>Alkylation of 1<i>H</i>-Indole with Electron-Deficient Alkenes Promoted by Zinc Acetate
  作者：Harshadas Mitaram Meshram、Dachepally Aravind Kumar、Bandi Chennakesava Reddy

  DOI：10.1002/hlca.200800410

  日期：2009.5

  Abstractmagnified imageAn efficient method for the Friedel–Crafts alkylation of 1H‐indole with nitro alkenes in the presence of zinc acetate is described. The procedure is applicable to a variety of nitro alkenes and substituted indoles, and the yields are very high.
• Turning On Catalysis: Incorporation of a Hydrogen-Bond-Donating Squaramide Moiety into a Zr Metal–Organic Framework
  作者：C. Michael McGuirk、Michael J. Katz、Charlotte L. Stern、Amy A. Sarjeant、Joseph T. Hupp、Omar K. Farha、Chad A. Mirkin

  DOI：10.1021/ja511403t

  日期：2015.1.21

  Herein, we demonstrate that the incorporation of an acidic hydrogen-bond-donating squaramide moiety into a porous UiO-67 metal-organic framework (MOF) derivative leads to dramatic acceleration of the biorelevant Friedel-Crafts reaction between indole and beta-nitrostyrene. In comparison, it is shown that free squaramide derivatives, not incorporated into MOF architectures, have no catalytic activity. Additionally, using the UiO-67 template, we were able to perform a direct comparison of catalytic activity with that of the less acidic urea-based analogue. This is the first demonstration of the functionalization of a heterogeneous framework with an acidic squaramide derivative.
• Synthesis of 3-(2-Nitroalkyl)pyrroles from Sulfonylpyrroles and their Conversion to 6-Azaindole Derivatives
  作者：Stefano Lancianesi、Alessandro Palmieri、Marino Petrini

  DOI：10.1002/adsc.201300701

  日期：2013.11.11

  AbstractThe reaction of sulfonylpyrroles with nitroalkanes in the presence of KF/alumina generates 3‐(2‐nitroalkyl)pyrroles in good yields. These compounds can be converted into trisubstituted 6‐azaindoles by a sequence of reactions comprising reduction of the nitro group, Pictet–Spengler cyclization and final oxidative aromatization.magnified image