1-[2-(三氟甲基)苯基]吡咯 | 89108-30-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1-[2-(三氟甲基)苯基]吡咯
• 英文名称: 1-<(2-trifluoromethyl)phenyl>pyrrole
• 英文别名: 1-[2-(trifluoromethyl)phenyl]-1H-pyrrole；1-[2-(trifluoromethyl)phenyl]pyrrole；1H-Pyrrole, 1-[2-(trifluoromethyl)phenyl]-
• CAS: 89108-30-5
• 化学式: C₁₁H₈F₃N
• mdl: MFCD02665223
• 分子量: 211.186
• InChiKey: IUMZRHODYBOXLA-UHFFFAOYSA-N

物化性质

• 沸点：
  62℃/1.13mm

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[2-(三氟甲基)苯基]吡咯 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.08h， 生成 1-[2-(trifluoromethyl)phenyl]-1H-pyrrole-2,5-dicarboxylic acid
  参考文献：
  名称：

  Useful, regioflexible methods for functionalization of 1-phenylpyrrole derivatives

  摘要：

  Highly regioselective mono-, di- and tribrominations of 1-[2-(trifluoromethyl)phenyl]-1H-pyrrole and several derivatives were accomplished with N-bromosuccinimide under mild conditions. Combined applications of these brominations with organometallic (e.g., bromine/lithium exchange or metalation) reactions provided a novel regioflexible route to new multifunctionalised 1-phenylpyrrole derivatives. The structures of the new products were determined by spectroscopic methods and confirmed in three cases with single crystal X-ray diffraction measurements. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.070
• 作为产物：
  描述：

  2,5-二甲氧基四氢呋喃 、 邻氨基三氟甲苯 在 溶剂黄146 作用下， 生成 1-[2-(三氟甲基)苯基]吡咯
  参考文献：
  名称：

  一种新颖且方便的制备5-（二苯基亚甲基）-1 H-吡咯-2（5 H）-的方法；综合与机理研究

  摘要：

  通过顺序二溴化和选择性有机金属溴/锂交换随后反应，已经开发了一种有效的区域选择性合成方法，用于从易于获得的1 H-吡咯中制备5-（二苯基亚甲基）-1 H-吡咯-2（5 H）-酮。与二苯甲酮。各种N-取代基的比较显示出对转化为官能团的高耐受性。通过光谱法确定新产物的结构，并通过单晶X射线衍射测量证实。此外，还对环内双键的反应机理和选择性官能化进行了理论研究。

  DOI：

  10.1016/j.tet.2016.07.032

文献信息

• Effect of a trifluoromethyl group on molecular structure: Competitive mono- and dilithiation of 1-[(trifluoromethyl)phenyl]pyrroles
  作者：Ferenc Faigl、Katalin Fogassy、Erzsébet Szűcs、Krisztina Kovács、György M Keserű、Veronika Harmat、Zsolt Böcskei、László Tőke

  DOI：10.1016/s0040-4020(99)00398-1

  日期：1999.6

  subsequent carboxylation of 1-[(trifluoromethyl)phenyl]pyrroles the mono- and the dicarboxylated derivatives were selectively prepared. The regioselective formation of the monocarboxylic acids could be rationalized in the light of the data collected from the literature. Explanation of the other phenomena, such as regioselective dilithiation and the strong effect of the trifluoromethyl group on the structure

  根据1-[（（三氟甲基）苯基]吡咯的锂化和随后的羧化过程中所用的条件，选择性地制备了单-和二羧化的衍生物。根据从文献中收集的数据，可以合理化单羧酸的区域选择性形成。借助于分子建模和单晶X射线测量，已阐明了其他现象的解释，例如区域选择性二氢脱硅和三氟甲基对邻位吡咯环的结构和芳香性的强大影响。
• Efficient synthesis and resolution of (±)-1-[2-carboxy-6-(trifluoromethyl)phenyl]pyrrole-2-carboxylic acid
  作者：Katalin Fogassy、Veronika Harmat、Zsolt Böcskei、Gábor Tárkányi、László Tőke、Ferenc Faigl

  DOI：10.1016/s0957-4166(00)00449-3

  日期：2000.12

  novel, efficient synthesis and resolution of (±)-1-[2-carboxy-6-(trifluoromethyl)-phenyl]pyrrole-2-carboxylic acid has been developed for the preparation of new members of optically active atropisomers. The e.e. values were determined by a highly sensitive 19F NMR spectroscopic method using β-cyclodextrin as chiral complexing agent. Single-crystal X-ray structures of the two diastereoisomeric salts and

  已经开发了新颖，有效的合成和拆分（±）-1- [2-羧基-6-（三氟甲基）-苯基]吡咯-2-羧酸的方法，用于制备旋光性阻转异构体的新成员。ee值使用β-环糊精作为手性络合剂，通过高灵敏度的19 F NMR光谱法测定。两种非对映异构体盐的单晶X射线结构，因此，也报道了对映异构体的绝对构型。
• Phenylpyrroles, a new chemolibrary virtual screening class of 5-HT7 receptor ligands
  作者：Magalie Paillet-Loilier、Frédéric Fabis、Alban Lepailleur、Ronan Bureau、Sabrina Butt-Gueulle、François Dauphin、Catherine Delarue、Hubert Vaudry、Sylvain Rault

  DOI：10.1016/j.bmcl.2005.05.059

  日期：2005.8

  Virtual screening studies have identified a series of phenylpyrroles as novel 5-HT7 receptor ligands. The synthesis and the affinity for the 5-HT7 receptor of these phenylpyrroles are described. Some of these compounds exhibited high affinity for the 5-HT7 receptors. (c) 2005 Elsevier Ltd. All rights reserved.
• Nano Sulfated Titania as a Heterogeneous Solid Acid Catalyst for the Synthesis of Pyrroles by Clauson–Kaas Condensation under Solvent-free Conditions
  作者：M. Hosseini-Sarvari、S. Najafvand-Derikvandi、A. Jarrahpour、R. Heiran

  DOI：10.1007/s10593-014-1425-3

  日期：2014.3

  A new and environmentally benign method for the preparation of N-substituted pyrroles from one-pot condensation reaction of 2,5-dimethoxytetrahydrofuran with amines and diamines in the presence of nano sulfated titania under solvent-free conditions is presented. This new protocol features simple operation, easy availability, stability, and eco-friendliness of catalyst, as well as high to excellent yields of products. In addition, we report for the first time an alternative method for the synthesis of pyrroles from aromatic amines containing the beta-lactam fragment using nano sulfated titania as catalyst.