2-(3-pyrrolyl)-2-phenylethanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-(3-pyrrolyl)-2-phenylethanol
• 英文别名: 2-phenyl-2-(1H-pyrrol-3-yl)ethanol
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: CGRRGIINMRGVST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 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：
  36
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  氧化苯乙烯 、 吡咯 在 tetrafluoroboric acid 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 2-(2-pyrrolyl)-2-phenylethanol 、 2-(3-pyrrolyl)-2-phenylethanol
  参考文献：
  名称：

  氟硼酸吸附在硅胶上与氮杂环催化环氧化物的区域选择性开环

  摘要：

  在温和的条件下，在催化量的HBF 4 -SiO 2存在下，可以与氮杂环（如吲哚，吡咯和咪唑）以区域选择性和高效的方式打开芳基环氧化物，从而以高收率和高收率得到相应的C-烷基化衍生物高区域选择性。

  DOI：

  10.1016/j.tetlet.2006.10.118

文献信息

• Magnetic nano Fe3O4 and CuFe2O4 as heterogeneous catalysts: A green method for the stereo- and regioselective reactions of epoxides with indoles/pyrroles
  作者：Ramarao Parella、Naveen、Srinivasarao Arulananda Babu

  DOI：10.1016/j.catcom.2012.09.030

  日期：2012.12

  this paper, we report a new solvent-free catalytic method using the magnetic nano Fe3O4 and CuFe2O4 as competent heterogeneous catalysts for the stereo- and regioselective reactions of epoxides with indoles/pyrroles, which gave the C-alkylated indoles/pyrroles. Chiral epoxides gave the alkylated indoles with a complete inversion of stereochemistry.

  在本文中，我们报告了一种新的无溶剂催化方法，该方法使用磁性纳米Fe 3 O 4和CuFe 2 O 4作为有效的非均相催化剂，用于环氧化物与吲哚/吡咯的立体和区域选择性反应，使C-烷基化吲哚/吡咯。手性环氧化物使烷基化的吲哚具有完全的立体化学转化。
• Friedel-Crafts Alkylation of Nitrogen Heterocycles Using [Bmim][OTf] as a Catalyst and Reaction Medium
  作者：M. Kantam、Rajashree Chakravarti、B. Sreedhar、Suresh Bhargava

  DOI：10.1055/s-2008-1078423

  日期：2008.6

  Friedel-Crafts alkylation of nitrogen heterocycles, such as indoles and pyrroles, can be carried out in ionic liquids under mild conditions to afford the corresponding alkylated product in moderate to good yields

  氮杂环（如吲哚和吡咯）的 Friedel-Crafts 烷基化可以在温和条件下在离子液体中进行，以中等至良好的收率提供相应的烷基化产物
• Indium Tribromide Catalyzed Highly Regioselective Ring Opening of Epoxides and Aziridines with Pyrrole
  作者：J. S. Yadav、B. V. S. Reddy、G. Parimala

  DOI：10.1055/s-2002-32575

  日期：——

  Pyrrole reacts smoothly with terminal epoxides in the presence of a catalytic amount of InBr3 under very mild conditions to afford the corresponding C-alkylated pyrroles in high yields. Similarly, activated aziridines also opened by pyrrole under the influence of indium tribromide to afford 2- and 3-alkyl pyrrole derivatives in high yields with high regioselectivity.

  吡咯在非常温和的条件下，在催化量的三溴化铟的存在下，与末端环氧化物顺利反应，生成相应的C-烷基化吡咯，产率较高。同样，在三溴化铟的影响下，活化的氮杂环也被吡咯打开，生成2-和3-烷基吡咯衍生物，产率高且具有很高的区位选择性。
• A facile synthesis of alkylated nitrogen heterocycles catalysed by 3D mesoporous aluminosilicates with cage type pores in aqueous medium
  作者：Rajashree Chakravarti、Pranjal Kalita、S. Tamil Selvan、Hamid Oveisi、V. V. Balasubramanian、M. Lakshmi Kantam、Ajayan Vinu

  DOI：10.1039/b914628h

  日期：——

  Friedel–Crafts alkylation of nitrogen heterocycles such as indoles and pyrroles with epoxides has been efficiently carried out using cage-type mesoporous aluminosilicates as recyclable catalysts in water under environmentally benign and mild conditions.

  弗里德尔工艺 烷基化 的 氮 使用笼型中孔铝硅酸盐作为可回收材料有效地进行了吲哚和吡咯等环氧化物的杂环 催化剂 在 水 在环境友好和温和的条件下。
• High-Pressure Organic Chemistry. 19. High-Pressure-Promoted, Silica Gel-Catalyzed Reaction of Epoxides with Nitrogen Heterocycles¹^,
  作者：Hiyoshizo Kotsuki、Katsunori Hayashida、Tomoyasu Shimanouchi、Hitoshi Nishizawa

  DOI：10.1021/jo951106t

  日期：1996.1.1

  The reaction of epoxides with nitrogen heterocycles such as indoles, pyrroles, imidazoles, and pyrazoles was studied under both high-pressure and silica gel-catalyzed conditions. Whereas it has been reported that the treatment of indole with styrene aside at in kbar and 42 degrees C for 24 h gave 2-(3-indolyl)-2-phenylethanol in 56% yield, the same compound was obtained in 88% yield when the reaction was conducted on silica gel at rt for 1 week. Similarly, efficient reaction of epoxides with pyrroles, imidazoles, and pyrazoles was achieved. In terms of stereochemical features, the epoxide ring opening reaction of (R)-(+)-styrene oxide with indole was found to proceed stereoselectively in an S(N)2 fashion at the benzyl carbon, in either ease.