1-[4-(三氟甲基)苯基]-1H-吡咯 | 92636-38-9

• 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-[4-(三氟甲基)苯基]-1H-吡咯
• 英文名称: 1-(4-(trifluoromethyl)phenyl)-1H-pyrrole
• 英文别名: 1-(4-(trifluoromethyl)phenyl)pyrrole；1-[4-(trifluoromethyl)phenyl]-1H-pyrrole；1-[4-(trifluoromethyl)phenyl]pyrrole
• CAS: 92636-38-9
• 化学式: C₁₁H₈F₃N
• mdl: MFCD01567129
• 分子量: 211.186
• InChiKey: JFGOCJGHXODFKU-UHFFFAOYSA-N

物化性质

• 熔点：
  107-111
• 沸点：
  152/53mm
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 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

安全信息

• 危险品标志：
  Xi
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  1-[4-(三氟甲基)苯基]-1H-吡咯 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.25h， 生成 N-[2-(4-Chloro-phenyl)-ethyl]-2-hydroxy-2-[1-(4-trifluoromethyl-phenyl)-1H-pyrrol-2-yl]-acetamide
  参考文献：
  名称：

  2-Oxo-2-(phen-2-ylpyrrol-2-yl)acetamides as potential anxiolytic agents: Synthesis and affinity at the central benzodiazepine receptor

  摘要：

  A series N-substituted 2-hydroxy and 2-oxo-2-(phen-1-ylpyrrol-2-yl)acetamides were synthesized and their affinity at the benzodiazepine receptor tested. Isosteric replacement of the indolyl ring in previously described derivatives by a phen-1-ylpyrrole led to the synthesis of seven compounds 8-9, 12-14, 23 and 26 with benzodiazepine affinity (K-1 less than or equal to 0.90 mu M). Among these, 26 exhibits an interesting anxiolytic activity and weak lateral effects. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80009-3
• 作为产物：
  描述：

  4-硝基三氟甲苯 在 盐酸 、 indium 作用下， 以 水 为溶剂， 反应 1.17h， 生成 1-[4-(三氟甲基)苯基]-1H-吡咯
  参考文献：
  名称：

  Novel Approach for the Synthesis ofN-Substituted Pyrroles Starting Directly from Nitro Compounds in Water

  摘要：

  A novel approach for a facile high-yielding synthesis of N-substituted pyrroles has been discovered by the treatment of nitroarenes with 2,5-dimethoxytetrahydrofuran using indium in dilute aqueous HCl at room temperature.

  DOI：

  10.1080/00397911.2010.526748

文献信息

• GaCl₃-Catalyzed C–H Cyanation of Indoles with <i>N</i>-Cyanosuccinimide
  作者：Xue Wang、Mohamed Makha、Shu-Wei Chen、Huaiji Zheng、Yuehui Li

  DOI：10.1021/acs.joc.9b00416

  日期：2019.5.17

  An efficient GaCl3-catalyzed direct cyanation of indoles and pyrroles using bench-stable electrophilic cyanating agent N-cyanosuccinimide was achieved and afforded 3-cyanoindoles and 2-cyanopyrroles in good yields and excellent regioselectivities. Notably, this protocol exhibited high reactivity for unprotected indoles and was applicable to a broad range of indole and pyrrole substrates.

  获得了使用台式稳定的亲电氰化剂N-氰基琥珀酰亚胺有效地GaCl 3催化的吲哚和吡咯直接氰化，并以良好的收率和优异的区域选择性提供了3-氰基吲哚和2-氰基吡咯。值得注意的是，该方案对未保护的吲哚表现出高反应性，并且适用于多种吲哚和吡咯底物。
• Catalytic Methylation of CH Bonds Using CO₂and H₂
  作者：Yuehui Li、Tao Yan、Kathrin Junge、Matthias Beller

  DOI：10.1002/anie.201405779

  日期：2014.9.22

  Formation of CC bonds from CO2 is a much sought after reaction in organic synthesis. To date, other than CH carboxylations using stoichiometric amounts of metals, base, or organometallic reagents, little is known about CC bond formation. In fact, to the best of our knowledge no catalytic methylation of CH bonds using CO2 and H2 has been reported. Described herein is the combination of CO2 and H2 for efficient

  由CO 2形成CC键是有机合成中非常需要的反应。迄今为止，除了使用化学计算量的金属，碱或有机金属试剂进行的CH羧化反应外，对CC键的形成知之甚少。实际上，据我们所知，没有报道使用CO 2和H 2催化CH键的甲基化。本文描述的是CO 2和H 2的组合，用于碳亲核试剂（如吲哚，吡咯和富电子芳烃）的有效甲基化。使用低聚甲醛的对比实验显示出与CO 2相似的反应性/ H 2系统。
• l-(+)-Tartaric acid and choline chloride based deep eutectic solvent: An efficient and reusable medium for synthesis of N-substituted pyrroles via Clauson-Kaas reaction
  作者：Ping Wang、Fei-Ping Ma、Zhan-Hui Zhang

  DOI：10.1016/j.molliq.2014.07.015

  日期：2014.10

  l-(+)-Tartaric acid–choline chloride based deep eutectic solvent has been found to be an effective promoted medium for Clauson-Kaas reaction of aromatic amines and 2,5-dimethoxytetrahydrofuran. Structurally diverse N-substituted pyrroles were obtained in high to excellent yields under mild conditions. The deep eutectic solvent is inexpensive, non-toxic, reusable and biodegradable.

  已经发现，基于1 -（+）-酒石酸-氯化胆碱的低共熔溶剂是促进芳香胺和2,5-二甲氧基四氢呋喃的Clauson-Kaas反应的有效促进介质。在温和条件下以高产率至优异产率获得结构多样的N-取代的吡咯。该深共晶溶剂便宜，无毒，可重复使用且可生物降解。
• Rapid and Efficient Trifluoromethylation of Aromatic and Heteroaromatic Compounds Using Potassium Trifluoroacetate Enabled by a Flow System
  作者：Mao Chen、Stephen L. Buchwald

  DOI：10.1002/anie.201306094

  日期：2013.10.25

  Going to the source: The trifluoromethylation of aryl/heteroaryl iodides has been demonstrated using a flow system, thus enabling a rapid rate of reaction. A broad spectrum of trifluoromethylated compounds was prepared in good to excellent yields using CF3CO2K as the trifluoromethyl source. The process has the advantage of short reaction times and uses convenient [CF3] sources.

  追根溯源：芳基/杂芳基碘化物的三氟甲基化已被证明使用流动系统，从而实现快速反应。使用 CF 3 CO 2 K 作为三氟甲基源，以良好到极好的收率制备了广谱的三氟甲基化化合物。该方法具有反应时间短的优点并使用方便的[CF 3 ]源。
• Rational Design and Development of<scp>Low‐Price</scp>, Scalable,<scp>Shelf‐Stable</scp>and Broadly Applicable Electrophilic Sulfonium<scp>Ylide‐Based</scp>Trifluoromethylating Reagents
  作者：Yafei Liu、Yijing Ling、Hangming Ge、Long Lu、Qilong Shen

  DOI：10.1002/cjoc.202100107

  日期：2021.6

  reagents (trifluoromethyl)(4-nitrophenyl)bis(carbomethoxy)methylide (1g) and (trifluoromethyl)(3-chlorophenyl)bis(carbomethoxy)methylide (1j) through structure-activity study was described. Under mild conditions, reagent 1g reacted with β-ketoesters and silyl enol ethers to give α-trifluoromethylated-β-ketoesters or α-trifluoromethylated ketones in high yields. In addition, reagent 1g could serve as

  通过结构活性研究，描述了两种高反应性亲电三氟甲基化试剂（三氟甲基）（4-硝基苯基）双（羰基甲氧基）亚甲基（1g）和（三氟甲基）（3-氯苯基）双（羰基甲氧基）亚甲基（1j）的开发。在温和的条件下，试剂1g与β-酮酸酯和甲硅烷基烯醇醚反应，以高收率得到α-三氟甲基化的β-酮酸酯或α-三氟甲基化的酮。另外，试剂1g可以在可见光照射下用作多种三氟甲基化转变的三氟甲基自由基，包括富电子吲哚和吡咯和芳基亚磺酸钠的自由基三氟甲基化，以及苯乙烯衍生物的三氟甲基化双官能化。另一方面，作为补充，在还原偶联条件下，试剂1j与多种（杂）芳基碘化物反应以形成三氟甲基化的（杂）芳烃。