2-benzyl-5-hexyl-1H-pyrrole | 650616-12-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-benzyl-5-hexyl-1H-pyrrole
• 英文别名: 2-benzyl-5-hexylpyrrole
• CAS: 650616-12-9
• 化学式: C₁₇H₂₃N
• 分子量: 241.376
• InChiKey: KURXCYOMRTWOOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-苄基-5-己基-1H-吡咯-3-羧酸乙酯 在 sodium hydroxide 作用下， 以 乙二醇 为溶剂， 反应 21.0h， 以65%的产率得到2-benzyl-5-hexyl-1H-pyrrole
  参考文献：
  名称：

  镓（III）和铟（III）盐介导的环丙烯和腈缩合的新合成吡咯。

  摘要：

  发现卤化镓（III）和铟（III）可介导环丙烯和腈的缩合，从而以中等收率得到吡咯衍生物。当存在过量的腈时，也会形成二氮杂pine。

  DOI：

  10.1039/b308875h

文献信息

• A sustainable catalytic pyrrole synthesis
  作者：Stefan Michlik、Rhett Kempe

  DOI：10.1038/nchem.1547

  日期：2013.2

  The pyrrole heterocycle is a prominent chemical motif and is found widely in natural products, drugs, catalysts and advanced materials. Here we introduce a sustainable iridium-catalysed pyrrole synthesis in which secondary alcohols and amino alcohols are deoxygenated and linked selectively via the formation of C–N and C–C bonds. Two equivalents of hydrogen gas are eliminated in the course of the reaction, and alcohols based entirely on renewable resources can be used as starting materials. The catalytic synthesis protocol tolerates a large variety of functional groups, which includes olefins, chlorides, bromides, organometallic moieties, amines and hydroxyl groups. We have developed a catalyst that operates efficiently under mild conditions. Pyrroles are a highly important class of compounds with a wide variety of applications in biochemistry, pharmacy and materials science. Here, an iridium-catalysed synthesis of pyrroles is described, starting from renewable resources, alcohols that may be derived from lignocellulosic feedstocks and amino alcohols. The reaction proceeds by a condensation reaction that liberates two equivalents of hydrogen gas.

  吡咯杂环是一种突出的化学基元，广泛存在于天然产物、药物、催化剂和先进材料中。本文介绍了一种可持续的铱催化吡咯合成方法，该方法通过形成C–N和C–C键，选择性地对二级醇和氨基醇进行脱氧耦合。反应过程中消除了两当量的氢气，并且可以完全使用可再生资源衍生的醇作为起始原料。催化合成方案能够耐受多种官能团，包括烯烃、氯化物、溴化物、有机金属基团、胺和羟基等。我们开发了一种在温和条件下高效运作的催化剂。吡咯是一类具有广泛应用的重要化合物，涉及生物化学、药物学和材料科学等领域。本文描述了一种从可再生资源出发，铱催化的吡咯合成方法，起始原料为来自木质纤维素原料的醇和氨基醇。该反应通过缩合反应释放两当量的氢气。
• Direct Synthesis of Pyrroles by Dehydrogenative Coupling of β-Aminoalcohols with Secondary Alcohols Catalyzed by Ruthenium Pincer Complexes
  作者：Dipankar Srimani、Yehoshoa Ben-David、David Milstein

  DOI：10.1002/anie.201300574

  日期：2013.4.2

  Pyrroles were synthesized in one step by using the acceptorless dehydrogenative coupling of amino alcohols with secondary alcohols (equivalent amounts), catalyzed by ruthenium pincer complexes (0.5 mol %) and a base (less than stoichiometric amounts) through selective CN and CC bond formation. This atom‐economical, environmentally friendly methodology offers easy access to a range of substituted

  吡咯是通过使用具有仲醇（当量），由钌钳形络合物（0.5摩尔％）催化的氨基醇的acceptorless脱氢偶联和碱（小于化学计量的量）通过选择性下，在一个步骤中合成 N和C  C键形成。这种原子经济，环保的方法可轻松获得中等至良好收率的一系列取代吡咯。
• A new synthesis of pyrroles by the condensation of cyclopropenes and nitriles mediated by gallium(iii) and indium(iii) salts
  作者：Shuki Araki、Takashi Tanaka、Shinya Toumatsu、Tsunehisa Hirashita

  DOI：10.1039/b308875h

  日期：——

  Gallium(III) and indium(III) halides were found to mediate the condensation of cyclopropenes and nitriles to give pyrrole derivatives in moderate yields. When excess nitrile was present, diazepine was also formed.

  发现卤化镓（III）和铟（III）可介导环丙烯和腈的缩合，从而以中等收率得到吡咯衍生物。当存在过量的腈时，也会形成二氮杂pine。