(2-methyl-5-phenyl-1H-pyrrol-3-yl)(phenyl)methanone | 13220-00-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-methyl-5-phenyl-1H-pyrrol-3-yl)(phenyl)methanone
• 英文别名: 2-methyl-3-benzoyl-5-phenyl-1H-pyrrole；(2-methyl-5-phenyl-pyrrol-3-yl)-phenyl-methanone；(2-methyl-5-phenyl-pyrrol-3-yl)-phenyl ketone；(2-Methyl-5-phenyl-pyrrol-3-yl)-phenyl-keton；3-Benzoyl-2-methyl-5-phenyl-pyrrol；(2-methyl-5-phenyl-1H-pyrrol-3-yl)-phenylmethanone
• CAS: 13220-00-3
• 化学式: C₁₈H₁₅NO
• 分子量: 261.323
• InChiKey: POPNUUPARHBNFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 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：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2-methyl-5-phenyl-1H-pyrrol-3-yl)(phenyl)methanone 、 4-氯氯苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 3.5h， 以70%的产率得到[1-(4-chlorobenzyl)-2-methyl-5-phenyl-1H-pyrrol-3-yl](phenyl)methanone
  参考文献：
  名称：

  Synthesis and characterization of a peripherally restricted CB1 cannabinoid antagonist, URB447, that reduces feeding and body-weight gain in mice

  摘要：

  Cannabinoid CB1 receptor antagonists reduce body weight in rodents and humans, but their clinical utility as anti-obesity agents is limited by centrally mediated side effects. Here, we describe the first mixed CB1 antagonist/CB2 agonist, URB447 ([4-amino-1-(4-chlorobenzyl)-2-methyl-5-phenyl-1H-pyrrol-3-yl]( phenyl) methanone), which lowers food intake and body-weight gain in mice without entering the brain or antagonizing central CB1-dependent responses. URB447 may provide a useful pharmacological tool for investigating the cannabinoid system, and might serve as a starting point for developing clinically viable CB1 antagonists devoid of central side effects. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.059
• 作为产物：
  描述：

  N-(4-benzoyl-2,5-diphenyl-2,3-dihydrofuran-2-yl)acetamide 在 manganese(III) triacetate dihydrate 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以86%的产率得到(2-methyl-5-phenyl-1H-pyrrol-3-yl)(phenyl)methanone
  参考文献：
  名称：

  碱诱导的2-氨基二氢呋喃和锰催化的好氧脱氢环的开环：获得功能化的恶唑

  摘要：

  通过使用空气作为绿色氧化剂，通过碱诱导的分子内C-O键裂解和形成，已经成功地从2-酰胺基二氢呋喃合成了功能化的恶唑。而且，这些官能化的恶唑可以容易地转化成相应的恶唑取代的吡唑和2 H-叠氮基。

  DOI：

  10.1021/acs.joc.7b00112

文献信息

• Development of a Gold-Multifaceted Catalysis Approach to the Synthesis of Highly Substituted Pyrroles: Mechanistic Insights via Huisgen Cycloaddition Studies
  作者：Simbarashe Ngwerume、William Lewis、Jason E. Camp

  DOI：10.1021/jo302349k

  日期：2013.2.1

  application of the Huisgen cycloaddition click reaction, which was used to probe the relative stability of substituted O-vinyloximes. The intermediacy of N-alkenylhydroxylamine O-vinyl ethers and imino ketones or imino aldehydes along the reaction pathway were determined by high-temperature 1H, 2H1H}, and 13C1H} NMR experiments. X-ray crystallographic evidence was used to further support the mechanistic hypothesis

  通过独立地优化工艺的两个关键步骤，开发了一种直接从肟和炔烃区域选择性合成高度取代的吡咯的金催化新方法。重要的是，阳离子金（I）物种显示出沿反应路径激活多个步骤，因此可作为多面催化剂。最初由金促进的肟氧向活化的炔烃的添加原位提供了O-乙烯基肟。该Ø随后通过金催化的互变异构，[3,3]-σ重排和环脱水过程将-乙烯基肟转化为吡咯。值得注意的是，该方法提供了酯在3/4位的形式的官能团手柄，以便进一步开发。拟议的机理途径得到了Huisgen环加成点击反应的新应用的支持，该反应被用于探测取代的O-乙烯基肟的相对稳定性。的中间性Ñ -alkenylhydroxylamine ø -乙烯基醚和沿反应途径亚氨基酮或亚氨基醛是由高温测定1 H，2 H ^ 1个H}，和13 C 11 H NMR实验。X射线晶体学证据被用来进一步支持机理假说。
• Palladium(<scp>ii</scp>)-catalysed regioselective synthesis of 3,4-disubstituted quinolines and 2,3,5-trisubstituted pyrroles from alkenes via anti-Markovnikov selectivity
  作者：Gopal Chandru Senadi、Wan-Ping Hu、Amol Milind Garkhedkar、Siva Senthil Kumar Boominathan、Jeh-Jeng Wang

  DOI：10.1039/c5cc05196g

  日期：——

  A novel strategy has been identified for the regioselective synthesis of 3,4-disubstituted quinolines and 2,3,5-trisubstituted pyrroles through anti-Markovnikov selectivity.

  通过反马尔科夫尼科夫选择性，已经确定了用于3,4-二取代的喹啉和2,3,5-三取代的吡咯的区域选择性合成的新策略。
• Mn(III)-Catalyzed Synthesis of Pyrroles from Vinyl Azides and 1,3-Dicarbonyl Compounds
  作者：Yi-Feng Wang、Kah Kah Toh、Shunsuke Chiba、Koichi Narasaka

  DOI：10.1021/ol802120u

  日期：2008.11.6

  Polysubstituted N-H pyrroles with a wide variety of substituents were prepared from vinyl azides and 1,3-dicarbonyl compounds by using Mn(III) complexes as catalysts.

  通过使用Mn（III）配合物作为催化剂，从叠氮化乙烯基和1,3-二羰基化合物制备具有多种取代基的多取代NH吡咯。
• Infrared heat aided solid state synthesis of pyrroles from 1,4-diketones and ammonium acetate
  作者：Chun Zhang、Jian Wang、Jing-Hua Li

  DOI：10.1002/jhet.744

  日期：2012.1

  A facile amination of 1,4‐diketones with ammonium acetate has been achieved by mechanochemical grinding assisted by infrared irradiation in the presence of silica gel. The wastes are reduced and the energy resources saved. J. Heterocyclic Chem., (2012).

  在硅胶存在下，通过红外辐射辅助的机械化学研磨，可以轻松地用乙酸铵胺化1,4-二酮。减少了浪费，节省了能源。J.杂环化​​学。（2012）。
• Visible <scp>Light‐Induced</scp> [3+2] Annulation Reaction of Alkenes with Vinyl Azides: Direct Synthesis of Functionalized Pyrroles
  作者：Ming Yang、Xin‐Yu Wang、Jie Wang、Yu‐Long Zhao

  DOI：10.1002/cjoc.202300498

  日期：2024.1.15

  photocatalytic [3+2] annulation of alkenes with vinyl azides was developed under irradiation by visible light in the presence of organic dye photocatalysts. Broad substrate scope and high functional group tolerance were demonstrated by more than 50 examples. The reaction provides a novel and efficient method for the synthesis of polyfunctionalized pyrroles under very mild metal-free conditions without other

  在有机染料光催化剂存在下，在可见光照射下，开发了烯烃与乙烯基叠氮化物的光催化[3+2]成环反应。 50 多个示例证明了广泛的底物范围和高官能团耐受性。该反应为在非常温和的无金属条件下、无需其他添加剂的情况下合成多官能化吡咯提供了一种新颖且有效的方法。