ethyl 2-methyl-1,4-diphenyl-1H-pyrrole-3-carboxylate | 94789-40-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 2-methyl-1,4-diphenyl-1H-pyrrole-3-carboxylate
• 英文别名: ethyl 2-methyl-1,4-diphenylpyrrole-3-carboxylate
• CAS: 94789-40-9
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: NCGCBYPFFBXXCG-UHFFFAOYSA-N

物化性质

• 沸点：
  459.4±45.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

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

反应信息

• 作为反应物：
  描述：

  ethyl 2-methyl-1,4-diphenyl-1H-pyrrole-3-carboxylate 、 二苯二硫醚 在 三氯异氰尿酸 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 以87%的产率得到ethyl 2-methyl-1,4-diphenyl-5-(phenylthio)-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Modular CeCl3·7H2O-catalyzed multi-component synthesis of 1,2,3,4-tetrasubstituted pyrroles under microwave irradiation and their further trichloroisocyanuric acid-mediated conversion into 5-sulfenylpyrrole derivatives

  摘要：

  A modular, multicomponent synthesis of 1,2,3,4-tetrasubstituted pyrroles promoted by the inexpensive CeCl3 center dot 7H(2)O, is reported. The reaction was carried out under microwave irradiation, affording good yields of products in short time. Scope and limitations were explored and a plausible reaction mechanism is discussed. The resulting heterocycles were smoothly and efficiently converted into their corresponding 5-arylsulfenyl derivatives by reaction with diaryl disulfides and trichloroisocyanuric acid in EtOAc. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.035
• 作为产物：
  描述：

  苯甲醛 在 2BF₄^(1-)*C₄₀H₄₀IrN₄⁽²⁺⁾ 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 18.5h， 生成 ethyl 2-methyl-1,4-diphenyl-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Synthesis of nitrogen heterocycles via α-aminoalkyl radicals generated from α-silyl secondary amines under visible light irradiation

  摘要：

  我们已成功地利用可见光介导合成了从α-硅烷二级胺衍生的α-氨基烷基自由基，用于加成到α,β-不饱和羰基化合物。所得的γ-氨基羰基化合物在一个锅过程中转化为γ-内酰胺和吡咯烷。

  DOI：

  10.1039/c4cc03000a

文献信息

• Regioselective Synthesis of 2,3,4-Trisubstituted Pyrroles via Pd(II)-Catalyzed Three-Component Cascade Reactions of Amines, Alkyne Esters, and Alkenes
  作者：Xu Zhang、Xuefeng Xu、Gong Chen、Wei Yi

  DOI：10.1021/acs.orglett.6b02325

  日期：2016.10.7

  three-component cascade reaction of diverse amines, alkyne esters, and alkenes is disclosed for the direct synthesis of diverse 2,3,4-trisubstituted pyrroles with broad functional group tolerance and in good to excellent yields. This transformation is supposed to proceed through the cascade formation of C(sp2)–C(sp2) and C(sp2)–N bonds via Pd(II)-catalyzed regioselective alkene migratory insertion, intramolecular

  公开了一种新颖，高效且通用的Pd（II）催化的多种胺，炔烃酯和烯烃的氧化三组分级联反应，用于直接合成具有宽泛的官能团耐受性的多种2,3,4-三取代的吡咯。产量高到极好。该转变被认为是通过Pd（II）催化的区域选择性烯烃迁移插入，分子内自由基加成和氧化顺序的级联形成C（sp 2）–C（sp 2）和C（sp 2）–N键而形成的。流程。
• Zirconocene dichloride catalysed one-pot synthesis of pyrroles through nitroalkene-enamine assembly
  作者：Sandeep Goyal、Jatinkumar K. Patel、Mukesh Gangar、Kapil Kumar、Vipin A. Nair

  DOI：10.1039/c4ra09873k

  日期：——

  Zirconocene dichloride was found to be a highly efficient catalyst for the synthesis of multi-substituted pyrroles by a three-component, one-pot reaction.

  锆二氯化物被发现是合成多取代吡咯烷的高效催化剂，通过三组分、一锅法反应。
• New magnetic-responsive deep eutectic catalyst based on Co2+/choline chloride for the synthesis of tetrahydro-pyrazolopyridines and pyrroles in water
  作者：Fatemeh Tamaddon、Ali Khorram

  DOI：10.1016/j.molliq.2020.112722

  日期：2020.4

  CoCl42− which provides magnetically recovering of Co4ChDES in cooperation with the four choline groups are hydrogen bond-acceptor and hydrogen bond-donor components of this DES. The 0.75 mol% and 1.5 mol% of Co4ChDES represented high catalytic performance in the water-based multi-component reactions (MCRs) for the synthesis of substituted tetrahydropyrazolopyridines (THDPPs) and pyrroles under very mild conditions

  通过筛选CoCl 2 ·6H 2 O和氯化胆碱（ChCl）的固液平衡混合物中不同摩尔比的组分，检测出一种新的磁响应深共晶（MDE），然后进行真空蒸发。在这些络合物中，蓝色络合物2ChCl·2Ch +：CoCl 4 2-（Co4ChDES），以1：4摩尔比的CoCl 2给出：ChCl表现出mp以及顺磁性的下降非常深。通过mp，UV-vis和FT-IR对所有络合物进行了比较，同时通过能量色散X射线光谱（EDX），振动样品磁强（VSM）和EDS作图对Co4ChDES进行了精细分析。Co4ChDES的正磁响应，表面元素分析和典型的UV-vis吸收波长证实了该DES结构中存在磁性四面体抗衡离子CoCl 4 2-。阴离子络合物CoCl 4 2-与四个胆碱基团一起提供Co4ChDES的磁性回收的是该DES的氢键受体和氢键供体组分。0.75 mol％和1.5 mol％的Co4ChDES在非常温和的条件下，
• An efficient and recyclable nanocatalyst for the green and rapid synthesis of biologically active polysubstituted pyrroles and 1,2,4,5-tetrasubstituted imidazole derivatives
  作者：Myo Thwin、Boshra Mahmoudi、Olga A. Ivaschuk、Qahtan A. Yousif

  DOI：10.1039/c9ra02325a

  日期：——

  for the green and rapid synthesis of biologically active polysubstituted pyrroles and 1,2,4,5-tetrasubstituted imidazoles derivatives using Cu@imine/Fe3O4 MNPs catalyst under solvent-free conditions is explained. This catalyst showed high reactivity for the synthesis of a set of different derivatives of polysubstituted pyrroles and 1,2,4,5-tetrasubstituted imidazole derivatives under appropriate reaction

  一种利用Cu@imine/Fe 3 O 4绿色快速合成生物活性多取代吡咯和1,2,4,5-四取代咪唑衍生物的有效工艺解释了无溶剂条件下的 MNPs 催化剂。该催化剂在适当的反应条件和较短的反应时间下，对合成一组不同的多取代吡咯衍生物和1,2,4,5-四取代咪唑衍生物表现出高反应性。此外，催化剂还被回收和重复使用六次，反应性和产率没有显着降低。与已报道的工艺相比，该方法始终表现出催化剂负载量低、反应时间短、产物易于分离纯化、收率高、催化剂的可回收性和可回收性高等优点。
• Synthesis of Pyrroles from β-Enamines and Nitroolefins Catalyzed by I₂ under High-speed Vibration Milling (HSVM)
  作者：Hui Xu、Yujin Li、Mengming Xing、Jianhong Jia、Liang Han、Qing Ye、Jianrong Gao

  DOI：10.1246/cl.141102

  日期：2015.4.5

  A solvent-free reaction, using a high-speed vibration milling (HSVM) technique, has been developed for the synthesis of polysubstituted pyrroles from β-enamines and nitroolefins as the raw materials, by using iodine as the catalyst. The influences of the vibration frequency and the reaction time were investigated and a series of 2,3,4-polysubstituted pyrroles were obtained in good yields at short reaction times (20 min) under the HSVM condition. It is an efficient, simple, and moderate approach for synthesizing polysubstituted pyrroles under the HSVM conditions.

  一种无溶剂反应，采用高速振动研磨（HSVM）技术，已经被开发用于从β-烯胺和硝基烯烃合成多取代吡啶，使用碘作为催化剂。研究了振动频率和反应时间的影响，在HSVM条件下，在短时间（20分钟）内获得了一系列产率良好的2,3,4-多取代吡啶。这是一种高效、简单且温和的方法，用于在HSVM条件下合成多取代吡啶。