1-(2,6-二甲基苯基)吡咯 | 15898-23-4

• 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-(2,6-二甲基苯基)吡咯
• 英文名称: 1-(2,6-dimethylphenyl)-1H-pyrrole
• 英文别名: 1-(2,6-Dimethylphenyl)-pyrrol；1-(2',6'-Xylyl)-pyrrol；1-(2,6-dimethylphenyl)pyrrole
• CAS: 15898-23-4
• 化学式: C₁₂H₁₃N
• mdl: MFCD03195931
• 分子量: 171.242
• InChiKey: BRHOVWCDYRJKAW-UHFFFAOYSA-N

物化性质

• 沸点：
  64-67 °C(Press: 0.5 Torr)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(2,6-二甲基苯基)吡咯 在 sodium tetrahydroborate 、 potassium hydroxide 、 三氯氧磷 作用下， 以 二氯甲烷 、 乙二醇甲醚 、 异丙醇 为溶剂， 生成 (E)-2-{[1-(2,6-dimethylphenyl)-1H-pyrrol-2-yl]-methylidene}allobetulin
  参考文献：
  名称：

  Synthesis of pyrrol-2-yl- and pyrazol-4-ylmethylidene derivatives of betulin and allobetulin

  摘要：

  Aldol-crotonic condensation of allobetulone and betulonic aldehyde with N-substituted pyrrole-2- and pyrazole-4-carbaldehydes afforded a series of new alpha,beta-unsaturated ketones of lupane series. Their reduction provided 2-ylidene derivatives of allobetulin and betulin, potential chiral components of liquid crystal materials. Structures of 1-phenyl-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbaldehyde, (E)-2-{[3-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-4-yl]methylidene}allobetulone, (E)-2-{[3-(4-bromophenyl)-1-phenyl-1H-pyrazol-4-yl]methylidene}-3-oxolup-20(29)-ene-28-carbaldehyde, (E)-2-{[3-(4-bromo-phenyl)-1-phenyl-1H-pyrazol-4-yl]methylidene}allobetulin, and (E)-2-{[3-(4-bromophe-nyl)-1-phenyl-1H-pyrazol-4-yl]-methylidene}lup-20(29)-ene-3,28-diol were established by X-ray diffraction (XRD) study.

  DOI：

  10.1134/s1070428015050231
• 作为产物：
  描述：

  N,N-diallyl-(2,6-dimethylphenyl)amine 在 Grubbs catalyst first generation 、 iron(III) chloride hexahydrate 、 氧气 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以28%的产率得到1-(2,6-二甲基苯基)吡咯
  参考文献：
  名称：

  一锅串联闭环易位反应和金属催化氧化脱氢反应从二烯丙基胺合成吡咯衍生物

  摘要：

  在O 2存在下，通过钌卡宾催化的闭环复分解反应和FeCl 3 ·6H 2 O或CuCl 2 ·2H 2 O催化的原位氧化脱氢反应，由二烯丙基胺合成了一系列芳基取代的吡咯衍生物。反应温和，简单，方便。在拟议的催化体系中，氧气气氛对于获得高取代的吡咯转化率起着至关重要的作用。

  DOI：

  10.1021/om400046r

文献信息

• Iron-Catalyzed Inexpensive and Practical Synthesis of N-Substituted Pyrroles in Water
  作者：Najmedin Azizi、Alireza Khajeh-Amiri、Hossein Ghafuri、Mohammad Bolourtchian、Mohammad Saidi

  DOI：10.1055/s-0029-1217799

  日期：2009.9

  An operationally simple, practical, and economical protocol for iron(III) chloride catalyzed Paal-Knorr pyrrole synthesis in water in good to excellent yields has been developed. Several N-substituted pyrroles are readily prepared from the reaction of 2,5-dimethoxytetrahydrofuran and aryl/alkyl, sulfonyl and acyl amines under very mild reaction conditions

  一种操作简便、实用且经济的实验方案已被开发，用于在水相中以铁(III)氯化物为催化剂进行Paal-Knorr吡咯合成，产率良好至优异。在非常温和的反应条件下，多个N-取代吡咯可以方便地通过2,5-二甲氧基四氢呋喃与芳基/烷基、磺酰基和酰基胺的反应来制备。
• Squaric acid catalyzed simple synthesis of N-substituted pyrroles in green reaction media
  作者：Najmadin Azizi、Anahita Davoudpour、Farshid Eskandari、Ehlham Batebi

  DOI：10.1007/s00706-012-0841-2

  日期：2013.3

  AbstractAn operationally simple and efficient protocol for squaric acid catalyzed synthesis of N-substituted pyrroles via the reaction of 2,5-dimethoxytetrahydrofuran and 2,5-hexandione with aryl amines in green reaction media (water, deep eutectic solvent, and polyethylene glycol) under ultrasound irradiation or thermal conditions in good to excellent yields has been developed. Graphical abstract

  摘要在绿色反应介质（水，深共熔溶剂和聚乙二醇）下，通过2,5-二甲氧基四氢呋喃和2,5-己二酮与芳胺的反应，对方酸催化合成N-取代的吡咯进行操作简单有效已经开发了具有良好产率的超声辐射或热条件。 图形概要
• 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。
• A <scp>solvent‐free manganese(II) ‐catalyzed Clauson‐Kaas</scp> protocol for the synthesis of <scp>N‐aryl</scp> pyrroles under microwave irradiation
  作者：Kizhakkekuttu Radhakrishnan Rohit、Gopinadh Meera、Gopinathan Anilkumar

  DOI：10.1002/jhet.4372

  日期：2022.1

  reaction for N-substituted pyrrole synthesis using 2,5-dimethoxytetrahydrofuran with variously substituted aromatic amines has been developed (up to 89% yield). This interesting neat strategy is free from additives including co-catalysts, ligands, and acids. Relatively low cost, environmentally benign, and handy Mn(NO3)2·4H2O is employed as the catalyst under microwave conditions with a very short reaction

  已经开发了第一个使用 2,5-二甲氧基四氢呋喃与各种取代的芳族胺合成 N-取代吡咯的锰催化改性 Clauson-Kaas 反应（产率高达 89%）。这种有趣的简洁策略不含添加剂，包括助催化剂、配体和酸。在微波条件下，使用成本相对较低、环境友好、方便的Mn(NO 3 ) 2 ·4H 2 O作为催化剂，反应时间非常短（20分钟）。上述品质证明了这种反应的绿色性质。
• Solvent Free Synthesis of N-Substituted Pyrrole Derivatives Catalyzed by Silica Sulfuric Acid
  作者：A. J. Khammas、C. Yolacan、F. Aydogan

  DOI：10.1134/s1070363218120332

  日期：2018.12

  Sulfuric acid immobilized on silica gel is used as an efficient catalyst in the synthesis of N-substituted pyrrole derivatives by the Clauson–Kaas pyrrole synthesis. The solvent free reaction mixture is stirred by grinding. Within very short reaction time the process leads to the corresponding products without any decomposition recorded.

  固定在硅胶上的硫酸在克劳森-卡斯（Clauson-Kaas）吡咯合成中被用作N-取代吡咯衍生物的有效催化剂。通过研磨搅拌无溶剂的反应混合物。在非常短的反应时间内，该过程可生成相应的产物，而未记录任何分解。