1-hexyl-2-phenyl-5-methylpyrrole | 533883-16-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-hexyl-2-phenyl-5-methylpyrrole
• 英文别名: 1-hexyl-2-methyl-5-phenyl-1H-pyrrole；1-Hexyl-2-methyl-5-phenylpyrrole
• CAS: 533883-16-8
• 化学式: C₁₇H₂₃N
• 分子量: 241.376
• InChiKey: AEHDOLSTDURMDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  正己胺 、 1-苯基-1,4-戊二酮 在 氯化胆碱 、 尿素 作用下， 反应 12.0h， 以91%的产率得到1-hexyl-2-phenyl-5-methylpyrrole
  参考文献：
  名称：

  Organic synthesis in deep eutectic solvents: Paal–Knorr reactions

  摘要：

  Deep eutectic solvents (the combination of either urea or glycerol with choline chloride) are effective solvents/catalysts for Paal-Knorr reactions to form pyrroles of furans. The reaction conditions are quite mild and do not require the addition of an additional Bronsted or Lewis acid catalyst. Given the inexpensive, non-toxic, and recyclable nature of the DES, these reaction conditions are simple and highly environmentally friendly. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.122

文献信息

• Acceptorless Dehydrogenative Coupling Using Ammonia: Direct Synthesis of N-Heteroaromatics from Diols Catalyzed by Ruthenium
  作者：Prosenjit Daw、Yehoshoa Ben-David、David Milstein

  DOI：10.1021/jacs.8b08385

  日期：2018.9.26

  The synthesis of N-heteroaromatic compounds via an acceptorless dehydrogenative coupling process involving direct use of ammonia as the nitrogen source was explored. We report the synthesis of pyrazine derivatives from 1,2-diols and the synthesis of N-substituted pyrroles by a multicomponent dehydrogenative coupling of 1,4-diols and primary alcohols with ammonia. The acridine-based Ru-pincer complex

  探索了通过直接使用氨作为氮源的无受体脱氢偶联过程合成 N-杂芳族化合物。我们报告了从 1,2-二醇合成吡嗪衍生物以及通过 1,4-二醇和伯醇与氨的多组分脱氢偶联合成 N-取代吡咯。吖啶基 Ru-钳形配合物 1 是这些转化的有效催化剂，其中吖啶主链转化为阴离子脱芳构化 PNP-钳形配体框架。
• Copper/Nitroxyl-Catalyzed Synthesis of Pyrroles by Oxidative Coupling of Diols and Primary Amines at Room Temperature
  作者：Weiru Fu、Lina Zhu、Shangzhi Tan、Zhengjia Zhao、Xiangzhu Yu、Lianyue Wang

  DOI：10.1021/acs.joc.2c01646

  日期：2022.10.7

  The Cu/ABNO-catalyzed aerobic oxidative coupling of diols and primary amines to access N-substituted pyrroles is highlighted (ABNO = 9-azabicyclo[3.3.1]nonane N-oxyl). The reaction proceeds at room temperature with an O2 balloon as the oxidant using commercially available materials as the substrates and catalysts. The catalyst system is characterized by a broad range of substrates and a good tolerance

  突出显示了 Cu/ABNO 催化的二醇和伯胺的需氧氧化偶联以获得 N 取代的吡咯（ABNO = 9-氮杂双环 [3.3.1] 壬烷N-氧基）。反应在室温下以 O 2气球作为氧化剂进行，使用市售材料作为底物和催化剂。该催化剂体系的特点是广泛的底物和对敏感官能团的良好耐受性。克级实验证明了该系统的实用性。
• Pyrrole synthesis
  申请人：Ohrlein Reinhold

  公开号：US20050014954A1

  公开（公告）日：2005-01-20

  The invention relates to a novel process for the preparation of N-substituted pyrroles, especially of formula (V), wherein the radicals are as defined in the description, by intermolecular aza-Wittig reaction starting from organic azides and 1,4-dioxo compounds. The invention relates also to novel iminophosphorane intermediates for this synthesis. The resulting pyrroles are useful, for example, in the organic synthesis of pharmaceuticals or other active substances and chemicals.

  本发明涉及一种以有机叠氮化物和 1,4-二氧代化合物为起点，通过分子间偶氮-维蒂希反应制备 N-取代的吡咯，特别是式 (V)，其中自由基如描述中所定义。本发明还涉及用于这种合成的新型亚氨基磷烷中间体。由此得到的吡咯类化合物可用于医药或其他活性物质和化学品的有机合成。
• PYRROLE SYNTHESIS
  申请人：Ciba Specialty Chemicals Holding Inc.

  公开号：EP1451179A1

  公开（公告）日：2004-09-01
• [EN] PYRROLE SYNTHESIS<br/>[FR] SYNTHESE DE PYRROLES
  申请人：CIBA SC HOLDING AG

  公开号：WO2003044011A1

  公开（公告）日：2003-05-30

  The invention relates to a novel process for the preparation of N-substituted pyrroles, especially of formula (V), wherein the radicals are as defined in the description, by intermolecular aza-Wittig reaction starting from organic azides and 1,4-dioxo compounds. The invention relates also to novel iminophosphorane intermediates for this synthesis. The resulting pyrroles are useful, for example, in the organic synthesis of pharmaceuticals or other active substances and chemicals.