1-(3-甲基苯基)吡咯 | 2437-43-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1-(3-甲基苯基)吡咯
• 英文名称: 1-(m-tolyl)-1H-pyrrole
• 英文别名: 1-(3-Methylphenyl)-1h-pyrrole；1-(3-methylphenyl)pyrrole
• CAS: 2437-43-6
• 化学式: C₁₁H₁₁N
• mdl: MFCD02665272
• 分子量: 157.215
• InChiKey: SQTCVIBAYYOZQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(3-甲基苯基)吡咯 、 3,4,5-三甲氧基苯甲酰氯 在 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.03h， 以80%的产率得到(1-(3-tolyl)-1H-pyrrol-3-yl)(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  New Pyrrole Derivatives with Potent Tubulin Polymerization Inhibiting Activity As Anticancer Agents Including Hedgehog-Dependent Cancer

  摘要：

  We synthesized 3-aroyl-1-arylpyrrole (ARAP) derivatives as potential anticancer agents having different substituents at the pendant 1-phenyl ring. Both the 1-phenyl ring and 3-(3,4,5-trimethoxyphenyl)carbonyl moieties were mandatory to achieve potent inhibition of tubulin polymerization, binding of colchicine to tubulin, and cancer cell growth. ARAP 22 showed strong inhibition of the P-glycoprotein-overexpressing NCI-ADR-RES and Messa/Dx5MDR cell lines. Compounds 22 and 27 suppressed in vitro the Hedgehog signaling pathway, strongly reducing luciferase activity in SAG treated NIH3T3 Shh-Light II cells, and inhibited the growth of medulloblastoma D283 cells at nanomolar concentrations. ARAPs 22 and 27 represent a new potent class of tubulin polymerization and cancer cell growth inhibitors with the potential to inhibit the Hedgehog signaling pathway.

  DOI：

  10.1021/jm500561a
• 作为产物：
  描述：

  3-硝基甲苯 在 盐酸 、 indium 作用下， 以 水 为溶剂， 反应 1.17h， 生成 1-(3-甲基苯基)吡咯
  参考文献：
  名称：

  Novel Approach for the Synthesis ofN-Substituted Pyrroles Starting Directly from Nitro Compounds in Water

  摘要：

  A novel approach for a facile high-yielding synthesis of N-substituted pyrroles has been discovered by the treatment of nitroarenes with 2,5-dimethoxytetrahydrofuran using indium in dilute aqueous HCl at room temperature.

  DOI：

  10.1080/00397911.2010.526748

文献信息

• Pd/Cu-catalyzed dual C–H bond carbonylation towards the synthesis of fluorazones
  作者：Fan Liao、Renyi Shi、Yuchen Sha、Jianhui Xia、Weilin Liao、Aiwen Lei

  DOI：10.1039/c7cc01707c

  日期：——

  Pd catalyzed oxidative dual C–H bond activation/carbonylation still remains a great challenge due to the generation of by-products via C–C bond formation. Herein, we developed a straightforward Pd/Cu-catalyzed oxidative dual C–H bond carbonylation process to access biologically and pharmaceutically important fluorazones from easily available N-aryl pyrroles and CO utilizing O₂ as the terminal oxidant.

  Pd催化的氧化性双C-H键活化/羰基化仍然是一个巨大挑战，因为会生成副产物通过C-C键形成。在这里，我们开发了一种直接的Pd/Cu催化的氧化性双C-H键羰基化过程，从易得的N-芳基吡咯和CO利用O2作为末端氧化剂，制备生物学和药用重要的氟酮。
• A manganese/copper bimetallic catalyst for C–N coupling reactions under mild conditions in water
  作者：Yong-Chua Teo、Fui-Fong Yong、Gina Shiyun Lim

  DOI：10.1016/j.tetlet.2011.10.128

  日期：2011.12

  An efficient and convenient bimetallic MnF2/CuI catalyst in combination with trans-1,2-diaminocyclohexane has been developed for the cross-coupling of nitrogen heterocycles with aryl halides in water at moderate temperature. A variety of nitrogen nucleophiles including pyrazole, 7-azaindole, indazole, indole, pyrrole and imidazole afforded the corresponding products in moderate to good yields (up to

  已经开发了一种有效且方便的双金属MnF 2 / CuI催化剂与反式-1,2-二氨基环己烷的组合，用于在中等温度下氮杂环与芳基卤化物的交叉偶联。在所述芳基化条件下，包括吡唑，7-氮杂吲哚，吲唑，吲哚，吡咯和咪唑在内的各种氮亲核试剂以中等至良好的收率（最高达94％）提供了相应的产物。
• NEW COMPOUNDS I/418
  申请人：Bjore Annika

  公开号：US20080015237A1

  公开（公告）日：2008-01-17

  There is provided compounds of formula I, wherein R 1 to R 7 have meanings given in the description, which are useful in the prophylaxis and in the treatment of arrhythmias, in particular atrial and ventricular arrhythmias.

  提供了式I的化合物， 其中R1至R7在描述中给出了它们的含义，这些化合物在预防和治疗心律失常方面非常有用，特别是房性和室性心律失常。
• A <scp>solvent‐free manganese(II) ‐catalyzed Clauson‐Kaas</scp> protocol for the synthesis of <scp>N‐aryl</scp> pyrroles under microwave irradiation
  作者：Kizhakkekuttu Radhakrishnan Rohit、Gopinadh Meera、Gopinathan Anilkumar

  DOI：10.1002/jhet.4372

  日期：2022.1

  reaction for N-substituted pyrrole synthesis using 2,5-dimethoxytetrahydrofuran with variously substituted aromatic amines has been developed (up to 89% yield). This interesting neat strategy is free from additives including co-catalysts, ligands, and acids. Relatively low cost, environmentally benign, and handy Mn(NO3)2·4H2O is employed as the catalyst under microwave conditions with a very short reaction

  已经开发了第一个使用 2,5-二甲氧基四氢呋喃与各种取代的芳族胺合成 N-取代吡咯的锰催化改性 Clauson-Kaas 反应（产率高达 89%）。这种有趣的简洁策略不含添加剂，包括助催化剂、配体和酸。在微波条件下，使用成本相对较低、环境友好、方便的Mn(NO 3 ) 2 ·4H 2 O作为催化剂，反应时间非常短（20分钟）。上述品质证明了这种反应的绿色性质。
• C5aR ANTAGONISTS
  申请人：Fan Pingchen

  公开号：US20100160320A1

  公开（公告）日：2010-06-24

  Compounds are provided that are modulators of the C5a receptor. The compounds are substituted piperidines and are useful in pharmaceutical compositions, methods for the treatment of diseases and disorders involving the pathologic activation of C5a receptors.

  提供了一些调节C5a受体的化合物。这些化合物是取代哌啶，并且在制药组合物、治疗涉及C5a受体病理性激活的疾病和疾病的方法中很有用。

表征谱图