(1-methyl-4-phenyl-1H-pyrrol-3-yl)(phenyl)methanone | 131911-12-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1-methyl-4-phenyl-1H-pyrrol-3-yl)(phenyl)methanone
• 英文别名: (1-Methyl-4-phenylpyrrol-3-yl)-phenylmethanone
• CAS: 131911-12-1
• 化学式: C₁₈H₁₅NO
• 分子量: 261.323
• InChiKey: FPHZCKDODMSWKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1-methyl-4-phenyl-1H-pyrrol-3-yl)(phenyl)methanone 在 polyphosphoric acid 作用下， 反应 0.5h， 以35%的产率得到(1-methyl-4-phenyl-1H-pyrrol-2-yl)(phenyl)methanone
  参考文献：
  名称：

  多磷酸介导的酰基迁移在邻域特异性合成由查尔酮组成的2-酰基吡咯中的应用

  摘要：

  本文报道了一种无金属合成2-酰基吡咯的方法。目标分子的合成从查耳酮开始，分两个步骤进行。第一步涉及通过与TosMIC反应将查尔酮转化为相应的4-取代3-酰基吡咯。在随后的步骤中，通过多磷酸介导的3酰基吡咯的酰基重排为其2酰基同类物，以中等至高收率获得了目标分子。至关重要的最后一步是在吡咯环上进行各种取代。初步的机制确定实验表明了lium离子的参与。

  DOI：

  10.1002/jhet.3494
• 作为产物：
  描述：

  反式-查耳酮 在 四丁基硫酸氢铵 氢氧化钾 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.25h， 生成 (1-methyl-4-phenyl-1H-pyrrol-3-yl)(phenyl)methanone
  参考文献：
  名称：

  The pyrrole moiety as a template for COX-1/COX-2 inhibitors

  摘要：

  Aroyl- and thiophene-substituted pyrrole derivatives have been synthesized as a new class of COX-1/COX-2 inhibitors. The inhibition of COX-1 was evaluated in a biological system using bovine PMNLs as the enzyme source, whereas LPS-stimulated human monocytes served as the enzyme source for inducible COX-2. The determination of the concentration of arachidonic acid metabolites was performed by HPLC for COX-1 and RIA for COX-2. Variation of the substitution pattern led to a series of active compounds which showed inhibition for COX-1 and COX-2. Structural requirements for the development of COX-1/COX-2 inhibitors are discussed, (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00150-1

文献信息

• Solvent-Controlled C2/C5-Regiodivergent Alkenylation of Pyrroles
  作者：Youla Su、Shang Gao、Yue Huang、Aijun Lin、Hequan Yao

  DOI：10.1002/chem.201502418

  日期：2015.10.26

  A solvent‐controlled C2/C5‐selective alkenylation of 3,4‐disubstituted pyrroles has been developed. The C3 substituent of pyrroles proved crucial to the regioselectivity. Substrates bearing directing groups at the C3 position exhibited excellent C2‐selectivities in chelation‐assisted CH activation in toluene or 1,4‐dioxane. However, a DMSO/DMF solvent system could override the chelation effect of

  已开发出一种由溶剂控制的3,4-二取代吡咯的C2 / C5选择性烯基化。吡咯的C 3取代基被证明对区域选择性至关重要。在甲苯或1,4-二恶烷中，在螯合辅助的CH活化中，在C3位置带有导向基团的底物表现出出色的C2选择性。但是，DMSO / DMF溶剂系统可以取代弱方向性基团（如羧酸根和羰基）的螯合作用，从而有利于对电子含量更高的C5位置的区域选择性。测试了一系列3-羧酸盐和3-羰基吡咯，显示出中等至良好的收率，对C2-和C5-烯基化过程均具有良好的区域选择性。
• Differential reactivity of β-amino enones and 3-dimethylaminoacrylaldehyde towards α-amino derivatives
  作者：Angel Alberola、José M. Andrés、Alfonso González、Rafael Pedrosa、Martina Vicente

  DOI：10.1039/p19900002681

  日期：——

  Unsubstituted β-amino enones react with α-amino derivatives by a well established route which implies a fast transamination process — 1,4-addition followed by elimination — and cyclodehydration of the intermediate to 3-functionalized pyrroles. In contrast, 3-dimethylaminoacrylaldehyde undergoes 1,2-addition followed by cyclization to give the final 2-substituted pyrroles. Isolation of the intermediates

  未取代的β-氨基烯酮通过一种完善的途径与α-氨基衍生物反应，这意味着快速的氨基转移过程-1,4-加成，然后消除-并将中间体环脱水为3-官能化的吡咯。相反，使3-二甲基氨基丙烯醛进行1，2-加成，然后环化，得到最终的2-取代的吡咯。中间体的分离为每种反应提供了建议的机理。
• A Direct Synthesis of 2-(Trimethylstannyl)pyrroles from Michael Acceptors and Stannylated Tosylmethyl Isocyanide¹
  作者：Harm P. Dijkstra、Ronald ten Have、Albert M. van Leusen

  DOI：10.1021/jo972216y

  日期：1998.8.1

  A series of 2-(trimethylstannyl)pyrroles 3, with substituents at the 3- and 4-positions, is synthesized efficiently by a base-induced reaction of stannylated TosMIC with Michael accepters. Stills cross-couplings with bromobenzene and double cross-couplings with 1,4-dibromobenzene have been achieved successfully with the N-methyl derivative (5a) and the N-Boc derivative (6a) of 3-benzoyl-2-(trimethylstannyl)-4-phenylpyrrole (3a), despite the bulk of these stannylpyrroles. Homo coupling reactions of the same stannylpyrroles with the corresponding bromopyrroles (prepared from stannylpyrroles 3 and NBS) were unsuccessful, probably for steric reasons.
• ALBEROLA, ANGEL;ANDRES, JOSE M.;GONZALEZ, ALFONSO;PEDROSA, RAFAEL;VICENTE+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N0, C. 2681-2685
  作者：ALBEROLA, ANGEL、ANDRES, JOSE M.、GONZALEZ, ALFONSO、PEDROSA, RAFAEL、VICENTE+

  DOI：——

  日期：——
• Application of Polyphosphoric Acid‐Mediated Acyl Migration for Regiospecific Synthesis of Diverse 2‐Acylpyrroles from Chalcones
  作者：Togiti Uday Kumar、Yadagiri Thigulla、Krishnan Rangan、Anupam Bhattacharya

  DOI：10.1002/jhet.3494

  日期：2019.4

  approach for the synthesis of 2‐acylpyrroles is reported in this paper. Synthesis of the target molecule started from chalcones and was carried out in two steps. Initial step involved the conversion of chalcones to corresponding 4‐substituted‐3‐acylpyrroles by reaction with TosMIC. In the subsequent step, target molecules were obtained in modest to good yields by polyphosphoric acid‐mediated acyl rearrangement

  本文报道了一种无金属合成2-酰基吡咯的方法。目标分子的合成从查耳酮开始，分两个步骤进行。第一步涉及通过与TosMIC反应将查尔酮转化为相应的4-取代3-酰基吡咯。在随后的步骤中，通过多磷酸介导的3酰基吡咯的酰基重排为其2酰基同类物，以中等至高收率获得了目标分子。至关重要的最后一步是在吡咯环上进行各种取代。初步的机制确定实验表明了lium离子的参与。