1-methyl-2,5-bis(4-methoxyphenyl)pyrrole | 104891-45-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-methyl-2,5-bis(4-methoxyphenyl)pyrrole
• 英文别名: 2,5-bis(4-methoxyphenyl)-1-methylpyrrole；N-methyl-2,5-di(4-methoxyphenyl)pyrrole；N-methyl-2,5-di(p-anisyl)pyrrole
• CAS: 104891-45-4
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: KLRBWYWVPVAWOV-UHFFFAOYSA-N

物化性质

• 沸点：
  434.4±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  23.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-甲基吡咯 、 4-氯苯甲醚 在 Pd(opiv)2 、 四丁基醋酸铵 、 cesium pivalate 作用下， 反应 20.0h， 以18%的产率得到1-methyl-2,5-bis(4-methoxyphenyl)pyrrole
  参考文献：
  名称：

  离子液体中无配体钯催化的吡咯的CH活化合成2,5-二芳基吡咯

  摘要：

  钯催化的CH活化和N-甲基吡咯和N-苯基吡咯的芳基化使得二芳基吡咯的合成方便。反应是通过使用乙酸四丁铵作为离子溶剂进行的，该反应可以通过使用简单的钯盐或聚乙烯吡咯烷酮稳定的钯纳米颗粒作为催化剂来应用无配体的催化体系。

  DOI：

  10.1002/cctc.201300099

文献信息

• Regioselective C-2 or C-5 Direct Arylation of Pyrroles with Aryl Bromides using a Ligand-Free Palladium Catalyst
  作者：Julien Roger、Henri Doucet

  DOI：10.1002/adsc.200900196

  日期：——

  acetyl or ester at the C-2 position of the pyrrole is tolerated. This environmentally attractive procedure has also been found to be tolerant to a very wide variety of functional groups on the aryl bromides such as formyl, acetyl, propionyl, ester, nitrile, nitro, fluoro, methoxy, amino or trifluoromethyl.

  据报道，通过CH键活化，吡咯的区域选择性C-2或C-5芳基化的简单且经济的方法。仅使用0.5-0.01 mol％的市售且无空气稳定的无配体的乙酸钯（II）[Pd（OAc）2 ]作为催化剂。容许在吡咯的C-2位置存在吸电子取代基，例如甲酰基，乙酰基或酯。还已经发现这种对环境有吸引力的方法可耐受芳基溴化物上的各种官能团，例如甲酰基，乙酰基，丙酰基，酯，腈，硝基，氟，甲氧基，氨基或三氟甲基。
• Eco-Friendly Solvents for Palladium-Catalyzed Desulfitative CH Bond Arylation of Heteroarenes
  作者：Anoir Hfaiedh、Kedong Yuan、Hamed Ben Ammar、Bechir Ben Hassine、Jean-François Soulé、Henri Doucet

  DOI：10.1002/cssc.201403429

  日期：2015.5.22

  Herein, we report the Pd‐catalyzed regioselective direct arylation of heteroarenes in which benzenesulfonyl chlorides are used as coupling partners through a desulfitative cross‐coupling that can be performed in diethyl carbonate (DEC) or cyclopentyl methyl ether (CPME) as green and renewable solvents or even in neat conditions instead of dioxane or dimethylacetamide (DMA). Under these solvent conditions

  本文中，我们报道了杂芳烃在钯催化的区域选择性直接芳基化反应中的应用，其中苯磺酰氯通过脱硫交叉偶联作用作为偶联伙伴，可在碳酸二乙酯（DEC）或环戊基甲基醚（CPME）中作为绿色和可再生溶剂进行甚至在纯净的条件下代替二恶烷或二甲基乙酰胺（DMA）。在这些溶剂条件下，反应与各种各样的杂芳烃进行。C2或C5芳基化产物是由呋喃和吡咯衍生物制得的。苯并呋喃还可以在C2位置进行芳基选择性芳基化，而如果使用噻吩和苯并噻吩，则反应会在C3或C4位置选择性地进行。此外，在某些情况下，尤其是对于1-甲基吲哚，
• Shurukhin, Yu. V.; Klyuev, N. A.; Grandberg, I. I., Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, p. 1883 - 1888
  作者：Shurukhin, Yu. V.、Klyuev, N. A.、Grandberg, I. I.

  DOI：——

  日期：——
• Intermediates in the Paal-Knorr synthesis of pyrroles
  作者：Venkataraman Amarnath、Douglas C. Anthony、Kalyani Amarnath、William M. Valentine、Lawrence A. Wetterau、Doyle G. Graham

  DOI：10.1021/jo00024a040

  日期：1991.11

  The mechanism of Paal-Knorr reaction between a 1,4-dicarbonyl compound and ammonia or a primary amine to form a pyrrole is explored. In aprotic solvents and in aqueous solutions near neutrality, d,l diastereomers of 3,4-dimethyl- and 3,4-diethyl-2,5-hexanediones (1r and 2r) formed pyrroles 1.3-57.0 times faster than the corresponding meso diastereomers (1m and 2m). This contradicts any intermediate, such as the enamine 15, which does not remain saturated at both the 3- and 4-positions through the rate-determining step. The demonstrated stereoisomeric difference in reactivity coupled with the following results support the hemiaminal (9) as the intermediate undergoing cyclization in the rate-limiting step of the Paal-Knorr reaction: (1) The reaction rate was adversely affected by increase in the size of the alkyl substituents on the dione. (2) Racemic 2,3-dimethyl-1,4-diphenyl-1,4-butanedione (3r) was more reactive toward ammonium acetate (2.2:1) and 2-aminoethanol (11.2:1) than the meso isomer (3m), ruling out the involvement of the less substituted enamine 14. (3) The relative rate of pyrrole formation of 1,4-diphenyl-1,4-butanedione (5) and its dimethoxy (6) and dinitro (7) derivatives (1:03:6) does not support cyclization of the imine (11) to the pyrrolinium ion (12). (4) The rates of reaction of 2,2,3,3-tetradeuterio-1,4-diphenyl-1,4-butanedione (5D) and perdeuterio-2,5-hexanedione (4D) were very close to those of unlabeled diketones, indicating the absence of a primary isotope effect in the reaction. (5) Neither the isomerization of the unreacted diastereomers of 1, 2, and 3 nor hydrogen exchange of 4D and 5D was detected during the reaction.