1-(1-phenylethyl)-1H-pyrrole | 17289-34-8

• 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-(1-phenylethyl)-1H-pyrrole
• 英文别名: 1-(1-phenylethyl)pyrrole
• CAS: 17289-34-8
• 化学式: C₁₂H₁₃N
• mdl: MFCD00970726
• 分子量: 171.242
• InChiKey: KEDQNBIZJNAJJP-UHFFFAOYSA-N

物化性质

• 沸点：
  252.0±9.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 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-(1-phenylethyl)-1H-pyrrole 、 2,5-己二酮 在 montmorillonite K-10 作用下， 反应 0.13h， 以75%的产率得到1-(1-phenylethyl)-4,7-dimethyl-1H-indole
  参考文献：
  名称：

  无溶剂的固体酸催化亲电退火：取代五元N-杂环合成的新绿色方法

  摘要：

  描述了在无溶剂条件下有效的微波诱导的，固体酸催化的环境友好的取代吡咯，吲哚和咔唑的合成。新的合成方法是基于使用相当强的固体酸K-10蒙脱石。胺的环烷基化以及吡咯和吲哚的脱嵌均在数分钟内完成，并提供了优异的产率（75–98％），选择性几乎为100％。

  DOI：

  10.1002/adsc.200606200
• 作为产物：
  描述：

  N,N-二烯丙基-1-苯基乙胺 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41%的产率得到1-(1-phenylethyl)-1H-pyrrole
  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

• Iron-Catalyzed Inexpensive and Practical Synthesis of N-Substituted Pyrroles in Water
  作者：Najmedin Azizi、Alireza Khajeh-Amiri、Hossein Ghafuri、Mohammad Bolourtchian、Mohammad Saidi

  DOI：10.1055/s-0029-1217799

  日期：2009.9

  An operationally simple, practical, and economical protocol for iron(III) chloride catalyzed Paal-Knorr pyrrole synthesis in water in good to excellent yields has been developed. Several N-substituted pyrroles are readily prepared from the reaction of 2,5-dimethoxytetrahydrofuran and aryl/alkyl, sulfonyl and acyl amines under very mild reaction conditions

  一种操作简便、实用且经济的实验方案已被开发，用于在水相中以铁(III)氯化物为催化剂进行Paal-Knorr吡咯合成，产率良好至优异。在非常温和的反应条件下，多个N-取代吡咯可以方便地通过2,5-二甲氧基四氢呋喃与芳基/烷基、磺酰基和酰基胺的反应来制备。
• Sustainable Manganese-Catalyzed Solvent-Free Synthesis of Pyrroles from 1,4-Diols and Primary Amines
  作者：Jannik C. Borghs、Yury Lebedev、Magnus Rueping、Osama El-Sepelgy

  DOI：10.1021/acs.orglett.8b03506

  日期：2019.1.4

  A general and selective metal-catalyzed conversion of biomass-derived primary diols and amines to the highly valuable 2,5-unsubstituted pyrroles has been developed. The reaction is catalyzed by a stable nonprecious manganese complex (1 mol %) in the absence of organic solvents whereby water and molecular hydrogen are the only side products. The manganese catalyst shows unprecedented selectivity, avoiding

  已经开发了一般的和选择性的金属催化的生物质衍生的伯二醇和胺到高度有价值的2，5-未取代的吡咯的转化。在没有有机溶剂的情况下，该反应由稳定的非贵金属锰配合物（1摩尔％）催化，其中水和分子氢是唯一的副产物。锰催化剂显示出前所未有的选择性，避免了吡咯烷，环状酰亚胺和内酯的形成。
• Solvent Free Synthesis of N-Substituted Pyrrole Derivatives Catalyzed by Silica Sulfuric Acid
  作者：A. J. Khammas、C. Yolacan、F. Aydogan

  DOI：10.1134/s1070363218120332

  日期：2018.12

  Sulfuric acid immobilized on silica gel is used as an efficient catalyst in the synthesis of N-substituted pyrrole derivatives by the Clauson–Kaas pyrrole synthesis. The solvent free reaction mixture is stirred by grinding. Within very short reaction time the process leads to the corresponding products without any decomposition recorded.

  固定在硅胶上的硫酸在克劳森-卡斯（Clauson-Kaas）吡咯合成中被用作N-取代吡咯衍生物的有效催化剂。通过研磨搅拌无溶剂的反应混合物。在非常短的反应时间内，该过程可生成相应的产物，而未记录任何分解。
• 1,5-DIARYLPYRROLE DERIVATIVES, PREPARATION METHOD THEREOF AND APPLICATION OF SAME IN THERAPEUTICS
  申请人：BARTH Francis

  公开号：US20080015245A1

  公开（公告）日：2008-01-17

  The invention relates to compounds having formula (I): Wherein X, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined herein. The invention also relates to a method of preparing said compounds and to die application thereof in therapeutics.

  该发明涉及具有以下结构式（I）的化合物：其中X，R1，R2，R3，R4，R5和R6如本文所定义。该发明还涉及一种制备所述化合物的方法以及在治疗中的应用。
• N-[(4,5-DIPHENYL-2-THIENYL)METHYL]AMINE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION
  申请人：DUCOUX Jean-Philippe

  公开号：US20080009543A1

  公开（公告）日：2008-01-10

  The subject of the present invention is compounds corresponding to formula (I): Wherein X, R 1 , R 2 , R 3 and R 4 are as described herein. The invention also relates to a method for the preparation and application of said compounds as cannabinoid CB1 receptor antagonists.

  本发明涉及与以下化学式（I）对应的化合物：其中X、R1、R2、R3和R4如本文所述。本发明还涉及一种用作大麻素CB1受体拮抗剂的化合物的制备和应用方法。