1-(2-甲氧基苯基)吡咯 | 89096-73-1

• 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-(2-甲氧基苯基)吡咯
• 英文名称: 1-(2-methoxyphenyl)-1H-pyrrole
• 英文别名: 1-(2-methoxyphenyl)pyrrole；1H-Pyrrole, 1-(2-methoxyphenyl)-
• CAS: 89096-73-1
• 化学式: C₁₁H₁₁NO
• mdl: MFCD02665273
• 分子量: 173.214
• InChiKey: RYGWXDNFNRUJFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2-甲氧基苯基)吡咯 在 二氯苯酚溴酯 、 四丁基碘化铵 、 三乙胺 作用下， 以 氯苯 为溶剂， 反应 24.0h， 以70%的产率得到2-(1H-吡咯-1-基)苯醇
  参考文献：
  名称：

  BN/BO-Ullazines 和 Bis-BO-Ullazines：BO 掺杂对芳香性和光电性能的影响

  摘要：

  我们已经实现了用两个 BO 单元或一个 BO 单元和一个 BN 单元对 ullazine 进行置换掺杂。这些 B 掺杂的 ullazing 的合成很简单，使用去甲基化和硼酸化环化作为关键步骤。BN/BO-ullazines ( 2 ) 和双-BO-ullazines ( 3 )的 Ullazine 核都非常接近于平面。通过紫外-可见光、荧光光谱、循环伏安法和密度泛函理论计算研究了它们的电子和光物理性质。

  DOI：

  10.1021/acs.joc.1c00777
• 作为产物：
  描述：

  Diallyl-(2-methoxy-phenyl)-amine 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 Aspergillus niger monoamine oxidase variant D₅ 作用下， 以 异辛烷 为溶剂， 反应 24.0h， 以84%的产率得到1-(2-甲氧基苯基)吡咯
  参考文献：
  名称：

  Unveiling the Biocatalytic Aromatizing Activity of Monoamine Oxidases MAO-N and 6-HDNO: Development of Chemoenzymatic Cascades for the Synthesis of Pyrroles

  摘要：

  A chemoenzymatic cascade process for the sustainable production of pyrroles has been developed. Pyrroles were synthesized by exploiting the previously unexplored aromatizing activity of monoamine oxidase enzymes (MAO-N and 6-HDNO). MAO-N/6-HDNO whole cell biocatalysts are able to convert 3-pyrrolines into pyrroles under mild conditions and in high yields. Moreover, MAO-N can work in combination with the ruthenium Grubbs catalyst, leading to the synthesis of pyrroles from diallylamines/-anilines in a one-pot cascade metathesis aromatization sequence.

  DOI：

  10.1021/acscatal.6b03081

文献信息

• Methyl-α-d-glucopyranoside as Green Ligand for Selective Copper-Catalyzed N-Arylation
  作者：Yuanguang Chen、Fangyu Du、Fengyang Chen、Qifan Zhou、Guoliang Chen

  DOI：10.1055/s-0039-1690702

  日期：2019.12

  selective N-arylation of amines or azoles with aryl halides­, methyl-α-d-glucopyranoside (MG) was found to function as a green ligand of copper powder. In addition, nitrogen heterocyclic amine compounds can also undergo the N-arylation coupling with heterocyclic aryl chlorides. This process allows access to a variety of aromatic amines and aryl azoles under mild reaction conditions, has good tolerance, and

  在胺或唑与芳基卤的选择性N-芳基化反应中，发现甲基-α - d-吡喃葡萄糖苷（MG）作为铜粉的绿色配体起作用。另外，氮杂环胺化合物还可与杂环芳基氯进行N-芳基化偶联。该方法允许在温和的反应条件下获得各种芳族胺和芳基唑，具有良好的耐受性，并且以中等至高收率进行。
• l-(+)-Tartaric acid and choline chloride based deep eutectic solvent: An efficient and reusable medium for synthesis of N-substituted pyrroles via Clauson-Kaas reaction
  作者：Ping Wang、Fei-Ping Ma、Zhan-Hui Zhang

  DOI：10.1016/j.molliq.2014.07.015

  日期：2014.10

  l-(+)-Tartaric acid–choline chloride based deep eutectic solvent has been found to be an effective promoted medium for Clauson-Kaas reaction of aromatic amines and 2,5-dimethoxytetrahydrofuran. Structurally diverse N-substituted pyrroles were obtained in high to excellent yields under mild conditions. The deep eutectic solvent is inexpensive, non-toxic, reusable and biodegradable.

  已经发现，基于1 -（+）-酒石酸-氯化胆碱的低共熔溶剂是促进芳香胺和2,5-二甲氧基四氢呋喃的Clauson-Kaas反应的有效促进介质。在温和条件下以高产率至优异产率获得结构多样的N-取代的吡咯。该深共晶溶剂便宜，无毒，可重复使用且可生物降解。
• Selective Palladium-Catalyzed Aminocarbonylation of Olefins to Branched Amides
  作者：Jie Liu、Haoquan Li、Anke Spannenberg、Robert Franke、Ralf Jackstell、Matthias Beller

  DOI：10.1002/anie.201605104

  日期：2016.10.17

  general and efficient protocol for iso‐selective aminocarbonylation of olefins with aliphatic amines has been developed for the first time. Key to the success for this process is the use of a specific 2‐phosphino‐substituted pyrrole ligand in the presence of PdX2 (X=halide) as a pre‐catalyst. Bulk industrial and functionalized olefins react with various aliphatic amines, including amino‐acid derivatives

  首次开发了使用脂肪族胺对烯烃进行异选择氨基羰基化的通用有效方法。该工艺成功的关键是在存在PdX 2（X =卤化物）作为前催化剂的情况下使用特定的2-膦基取代的吡咯配体。大量的工业化和官能化烯烃与各种脂肪胺（包括氨基酸衍生物）反应，通常以较高的收率（高达99％）和区域选择性（b / l高达99：1）得到相应的支链酰胺。
• Scandium triflate-catalysed synthesis of <i>N</i>-substituted pyrroles from amine and 2,5-dimethoxytetrahydrofuran
  作者：Bing Zuo、Jiuxi Chen、Miaochang Liu、Jinchang Ding、Huayue Wu、Weike Su

  DOI：10.3184/030823409x393628

  日期：2009.1

  The Clauson–Kass pyrrole synthesis catalysed by scandium triflate afforded N-substituted 2- and 3-unsubstituted pyrroles with yields ranged from good to excellent. Aromatic amines, heteroaomatic amines, 4-methylbenzenesulfonamide and 2-chlorobenzamide are good substrates in this transformation.

  由三氟甲磺酸钪催化的 Clauson-Kass 吡咯合成得到了 N-取代的 2-和 3-未取代的吡咯，产率从好到极好。芳香胺、杂胺、4-甲基苯磺酰胺和2-氯苯甲酰胺是这种转化的良好底物。
• Cu(II)-Catalyzed C-N Coupling of (Hetero)aryl Halides and N-Nucleophiles Promoted by α-Benzoin Oxime
  作者：Chunling Yuan、Lei Zhang、Yingdai Zhao

  DOI：10.3390/molecules24224177

  日期：——

  We first reported the new application of a translate metal chelating ligand α-benzoin oxime for improving Cu-catalyzed C-N coupling reactions. The system could catalyse coupling reactions of (hetero)aryl halides with a wide of nucleophiles (e.g., azoles, piperidine, pyrrolidine and amino acids) in moderate to excellent yields. The protocol allows rapid access to the most common scaffolds found in FDA-approved pharmaceuticals.

  我们首次报道了一种新的应用于改进铜催化的C-N偶联反应的金属螯合配体α-苯甲醛肟。该体系能够催化(hetero)芳基卤代物与各种亲核试剂（例如唑类化合物、哌啶、吡咯啉和氨基酸）的偶联反应，产率从中等到优良不等。该方案可快速获得FDA批准的药物中常见的骨架。