2-甲基-1,5-二苯基吡咯-3-甲酸乙酯 | 3652-61-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2-甲基-1,5-二苯基吡咯-3-甲酸乙酯
• 中文别名: 2-甲基-1,5-二苯基-1H-吡咯-3-羧酸乙酯
• 英文名称: ethyl 2-methyl-1,5-diphenyl-1H-pyrrole-3-carboxylate
• 英文别名: ethyl 2-methyl-1,5-diphenylpyrrole-3-carboxylate
• CAS: 3652-61-7
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: YHEGUULWFOVVRG-UHFFFAOYSA-N

物化性质

• 熔点：
  94 °C
• 稳定性/保质期：
  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 储存条件：
  请将药品存放在避光、通风且干燥的地方，并密封保存。

反应信息

• 作为反应物：
  描述：

  2-甲基-1,5-二苯基吡咯-3-甲酸乙酯 在 sodium hydroxide 、 copper(ll) bromide 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 28.0h， 生成 4-Bromo-2-methyl-1,5-diphenylpyrrole-3-carboxylic acid
  参考文献：
  名称：

  Petruso, S.; Caronna, S.; Sferlazzo, M., Journal of Heterocyclic Chemistry, 1990, vol. 27, # 5, p. 1277 - 1280

  摘要：

  DOI：
• 作为产物：
  描述：

  苯乙酮肟 在 copper(l) iodide 、 manganese(III) triacetate dihydrate 、 碳酸氢钠 、 对甲苯磺酸 作用下， 以 1,2-二氯乙烷 、 甲苯 、 乙腈 为溶剂， 反应 8.0h， 生成 2-甲基-1,5-二苯基吡咯-3-甲酸乙酯
  参考文献：
  名称：

  Direct Oxidative Coupling of Enamides and 1,3-Dicarbonyl Compounds: A Facile and Versatile Approach to Dihydrofurans, Furans, Pyrroles, and Dicarbonyl Enamides

  摘要：

  An efficient manganese(III)-mediated oxidative coupling reaction between a-aryl enamides and 1,3-dicarbonyl compounds has been developed. A series of dihydrofurans and dicarbonyl enamides were synthesized in moderate to good yields. Moreover, these dihydrofurans could be readily transformed into the corresponding furans and pyrroles via the Paal-Knorr reaction.

  DOI：

  10.1021/ol503009f

文献信息

• Novel and highly efficient preparation of pyrroles using supported ionic liquid ILCF3SO3@SiO2 as a heterogeneous catalyst
  作者：Yang Liu、Yu Lin Hu

  DOI：10.1007/s13738-018-1300-8

  日期：2018.5

  AbstractA supported ionic liquid ILCF3SO3@SiO2 was synthesized and used as a highly efficient catalyst in the Paal–Knorr reaction for the preparation of pyrroles. The heterogeneous catalyst could be easily recovered and recycled for five times without noticeable loss of catalytic activity. Also a possible reaction mechanism is provided. Graphical Abstract

  摘要合成了负载型离子液体ILCF 3 SO 3 @SiO 2，并在Paal-Knorr反应中用作制备吡咯的高效催化剂。该非均相催化剂可以容易地回收和再循环五次，而没有明显的催化活性损失。还提供了可能的反应机理。 图形概要
• <i>N</i>-Substituted pyrrole synthesis by Paal-Knorr condensation using recyclable cationic exchange resin in water
  作者：Yan-Hong He、Gang-Qiang Wang、Zhi Guan

  DOI：10.1002/jhet.317

  日期：——

  Cationic exchange resin has been utilized for the first time as a novel and recyclable heterogeneous catalyst for the synthesis of N‐substituted pyrroles from variety of 1,4‐diketones and aniline. This simple synthesis has been accomplished with excellent yields. The recovered catalyst can be reused for subsequent runs with only a gradual decrease in activity. J. Heterocyclic Chem., (2010).

  阳离子交换树脂首次作为一种新型的可循环使用的非均相催化剂用于由各种1,4-二酮和苯胺合成N取代的吡咯。已经以优异的产率完成了这种简单的合成。回收的催化剂可以重新使用，用于后续操作，而活性只会逐渐降低。J.杂环化​​学。（2010）。
• An Efficient Procedure for the Synthesis of Polysubstituted Pyrroles in an Ionic Liquid
  作者：Yan-Hong He、Gang-Qiang Wang、Ke-Ling Xu、Zhi Guan

  DOI：10.1515/znb-2011-0212

  日期：2011.2.1

  1-butyl-3-methyl-imidazolium hydrogen sulfate, [bmim]HSO4, was used as a catalyst and reaction medium for the pyrrole synthesis, and a wide range of aliphatic, aromatic, heteroaromatic and carboxylic 1,4-diketones easily underwent condensations with aniline and ethylenediamine to form polysubstituted pyrroles. Sequential decarboxylation/Paal-Knorr pyrrole condensation was observed, which provides a new

  离子液体 1-丁基-3-甲基-咪唑硫酸氢盐 [bmim]HSO4 用作吡咯合成的催化剂和反应介质，以及广泛的脂肪族、芳香族、杂芳香族和羧基 1,4-二酮容易与苯胺和乙二胺缩合形成多取代的吡咯。观察到顺序脱羧/Paal-Knorr 吡咯缩合，这为从 1,4-二酮-2,3-二羧酸酯制备单酯吡咯提供了一种新的、简便的方法。图形摘要 一种在离子液体中合成多取代吡咯的有效方法
• Copper-mediated cross-coupling–cyclization–oxidation: a one-pot reaction to construct polysubstituted pyrroles
  作者：Pei Liu、Jin-ling Liu、Heng-shan Wang、Ying-ming Pan、Hong Liang、Zhen-Feng Chen

  DOI：10.1039/c3cc48728h

  日期：——

  A novel and efficient procedure for the synthesis of polysubstituted pyrroles has been developed in this work. The polysubsituted pyrroles were synthesized directly from terminal alkenes, amines and β-keto esters through cross-coupling–cyclization–oxidation in the presence of a catalytic amount of cuprous chloride. This method provides a one-pot synthesis route from terminal alkenes to polysubstituted pyrroles for the first time and opens a new area in cuprous catalysis.

  本文开发了一种新颖且高效的多取代吡咯合成方法。多取代吡咯是通过与终端烯烃、胺和β-酮酯在少量氯化亚铜催化剂存在下进行交叉耦合-环化-氧化反应直接合成的。这种方法首次提供了从终端烯烃到多取代吡咯的一锅合成路线，为亚铜催化开辟了新领域。
• [EN] 1,5-DIARYL-PYRROLE-3-CARBOXAMIDE DERIVATIVES AND THEIR USE AS CANNABINOID RECEPTOR MODULATORS<br/>[FR] DERIVES DE 1,5-DIARYL-PYRROLE-3-CARBOXAMIDE ET LEUR UTILISATION EN TANT QUE MODULATEURS DES RECEPTEURS DES CANNABINOIDES
  申请人：ASTRAZENECA AB

  公开号：WO2004058249A1

  公开（公告）日：2004-07-15

  The present invention relates to a compound of formula (I) (A chemical formula should be inserted here - please see paper copy enclosed herewith) in which R1 and R2 independently represent phenyl, thienyl or pyridyl each of which is optionally substituted by one, two or three groups represented by Z; and R3 is H, a C1-3alkyl group, a C1-3alkoxymethyl group, trifluoromethyl, a hydroxyC1-3alkyl group, an aminoC1-3alkyl group, C1-3alkoxycarbonyl, carboxy, cyano, carbamoyl, mono or di C1-3alkylcarbamoyl, acetyl, or hydrazinocarbonyl of formula -CONHNRaRb wherein Ra and Rb are as defined for R4 and R5 respectively; X is CO or SO2 ; Y is absent or represents NH optionally substituted by a C1-3alkyl group; R4 and R5 independently represent: a C1-6alkyl group; an (amino)C1-4alkyl- group in which the amino is optionally substituted by one or more C1-3alkyl groups; an optionally substituted non-aromatic C3-15carbocyclic group; a (C3-12cycloalkyl)C1-3alkyl- group; a group -(CH2)r(phenyl )s; naphthyl; anthracenyl; a saturated 5 to 8 membered heterocyclic group containing one nitrogen and optionally one of the following: oxygen, sulphur or an additional nitrogen wherein the heterocyclic group is optionally substituted ;1-adamantylmethyl; a group - (CH2)t Het where Het represents an aromatic heterocycle optionally substituted; or R4 represents H and R5 is as defined above; or R4 and R5 together with the nitrogen atom to which they are attached represent a saturated 5 to 8 membered heterocyclic group; R6 is H, a C1-3alkyl group, a C1-3alkoxymethyl group, trifluoromethyl, a hydroxyC1-3alkyl group, C1-3alkoxycarbonyl, carboxy, cyano, carbamoyl, mono or di C1-3alkylcarbamoyl, acetyl, or hydrazinocarbonyl of formula -CONHNRaRb ; with provisos; to processes for preparing such compounds, to their use in the treatment of obesity, psychiatric and neurological disorders particularly obesity, to methods for their therapeutic use and to pharmaceutical compositions containing them.

  本发明涉及一种化合物，其化学式为（I），其中R1和R2分别独立表示苯基，噻吩基或吡啶基，每个基上均可选择性地取代一个、两个或三个由Z表示的基团；R3为H，C1-3烷基基团，C1-3烷氧甲基基团，三氟甲基，羟基C1-3烷基基团，氨基C1-3烷基基团，C1-3烷氧羰基，羧基，氰基，氨基甲酰基，一级或二级C1-3烷基甲酰基，乙酰基或化学式为-CONHNRaRb的肼基，其中Ra和Rb分别定义为R4和R5；X为CO或SO2；Y为空或表示NH，该氮原子可选择性地取代为C1-3烷基基团；R4和R5独立地表示：C1-6烷基基团；（氨基）C1-4烷基基团，其中氨基可选择性地取代为一个或多个C1-3烷基基团；可选择性取代的非芳香性C3-15碳环基团；（C3-12环烷基）C1-3烷基基团；基团-(CH2)r(苯) s；萘基；蒽基；含有一个氮原子并可选择性地含有以下之一的饱和的5到8个成员的杂环基团：氧，硫或另一个氮原子，其中杂环基团可选择性地取代；1-金刚烷基甲基；基团-(CH2)t Het，其中Het表示可选择性取代的芳香性杂环族；或者R4表示H，R5如上所定义；或者R4和R5与它们连接的氮原子一起表示饱和的5到8个成员的杂环基团；R6为H，C1-3烷基基团，C1-3烷氧甲基基团，三氟甲基，羟基C1-3烷基基团，C1-3烷氧羰基，羧基，氰基，氨基甲酰基，一级或二级C1-3烷基甲酰基，乙酰基或化学式为-CONHNRaRb的肼基；但需注意的是，本发明还涉及制备这种化合物的方法，以及它们在肥胖、精神和神经疾病特别是肥胖的治疗中的应用方法和包含它们的制药组合物。