1,2,3,5-四苯基吡咯 | 15345-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1,2,3,5-四苯基吡咯
• 英文名称: 1,2,3,5-tetraphenyl-pyrrole
• 英文别名: 1,2,3,5-tetraphenyl-1H-pyrrole；1,2,3,5-Tetraphenyl-pyrrol；1,2,3,5-tetraphenylpyrrole
• CAS: 15345-47-8
• 化学式: C₂₈H₂₁N
• 分子量: 371.481
• InChiKey: FGLPAVADAXUNOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1,2,3,5-四苯基吡咯 在 氨 作用下， 生成 嘧啶,2,4,6-三苯基-
  参考文献：
  名称：

  Capuano; Giammanco, Gazzetta Chimica Italiana, 1956, vol. 86, p. 119,125

  摘要：

  DOI：
• 作为产物：
  描述：

  苯基-苯基氨基-乙腈 在 氢氧化钾 、 乙醇 作用下， 生成 1,2,3,5-四苯基吡咯
  参考文献：
  名称：

  Clarke; Lapworth, Journal of the Chemical Society, 1907, vol. 91, p. 704

  摘要：

  DOI：

文献信息

• Visible-Light-Promoted Photocatalyst-Free Hydroacylation and Diacylation of Alkenes Tuned by NiCl₂·DME
  作者：Xinxin Zhao、Bing Li、Wujiong Xia

  DOI：10.1021/acs.orglett.9b04595

  日期：2020.2.7

  4-dihydropyridines via an acyl radical addition and hydrogen atom transfer pathway under photocatalyst-free conditions. The efficiency was highlighted by wide substrate scope, good to high yields, successful scale-up experiments, and expedient preparation of highly functionalized ketone derivatives. In addition, this protocol allows for the synthesis of 1,4-dicarbonyl compounds through alkene diacylation in the presence

  在这里，我们描述了一种可见光促进的加氢酰化策略，该策略有助于在无光催化剂的条件下，通过酰基加成和氢原子转移途径，从烯烃和4-酰基-1,4-二氢吡啶制备酮。广泛的底物范围，良好至高收率，成功的按比例放大实验以及方便地制备高度官能化的酮衍生物等突出了效率。另外，该方案允许在NiCl2·DME存在下通过烯烃二酰化反应合成1,4-二羰基化合物。
• Acyl Radicals from α-Keto Acids Using a Carbonyl Photocatalyst: Photoredox-Catalyzed Synthesis of Ketones
  作者：Da-Liang Zhu、Qi Wu、David James Young、Hao Wang、Zhi-Gang Ren、Hong-Xi Li

  DOI：10.1021/acs.orglett.0c02351

  日期：2020.9.4

  Acyl radicals have been generated from α-keto acids using inexpensive and commercially available 2-chloro-thioxanthen-9-one as the photoredox catalyst under visible light illumination. These reactive species added to olefins or coupled with aryl halides via a bipyridyl-stabilized Ni(II) catalyst, enabling easy access to a diverse range of ketones. This reliable, atom-economical, and eco-friendly protocol

  在可见光照射下，使用廉价且可商购的2-氯-噻吨酮-9-作为光氧化还原催化剂，已由α-酮酸生成了酰基基团。这些反应性物质通过联吡啶基稳定的Ni（II）催化剂添加到烯烃中或与芳基卤化物偶合，可轻松获得各种酮。这种可靠，原子经济且环保的协议可与多种官能团兼容。
• Nitrone Cycloadditions to 1,2-Diphenylcyclopropenes and Subsequent Transformations of the Isoxazolidine Cycloadducts
  作者：Vyacheslav V. Diev、Oksana N. Stetsenko、Tran Q. Tung、Jürgen Kopf、Rafael R. Kostikov、Alexander P. Molchanov

  DOI：10.1021/jo702379d

  日期：2008.3.1

  occurs with the formation of expected “normal” cycloadducts (with N-methylnitrones) and products of their subsequent transformations. Among them are corresponding α-acetophenyl aziridines and tetra (or penta) -arylpyrroles. Aziridines and the normal cycloadducts can be also thermally converted to such arylpyrroles with moderate to good yields. Substitution at the C3 position of cyclopropenes by an electron

  的1,3-偶极环加成Ç -芳基，ñ -芳基（或ñ -甲基）硝酮与一些1,2- diphenylcyclopropenes在C取代的3位置与预期的“正常” cycloadducts的形成（与发生ñ -甲基硝酮）及其后续转化的产物。其中有相应的α-乙酰苯基氮丙啶和四（或五）-芳基吡咯。氮丙啶和正常的环加合物也可以以中等至良好的产率热转化为这种芳基吡咯。电子受体基团取代环丙烯的C 3位会降低环丙烯的反应性。
• Synthesis of Tetrasubstituted Pyrroles from Homopropargylic Amines<i>via</i>a Sonogashira Coupling/Intramolecular Hydroamination/Oxidation Sequence
  作者：Chan Wang、Kaimeng Huang、Junying Wang、Hongkai Wang、Lingyan Liu、Weixing Chang、Jing Li

  DOI：10.1002/adsc.201500350

  日期：2015.9.14

  A one‐pot reaction of homopropargylic amines and aryl iodides was developed in the presence of a palladium (Pd) catalyst and generated a series of tetrasubstituted pyrrole derivatives in good to high yields. This process involved a Sonogashira, intramolecular hydroamination, cyclization and oxidation sequence of reactions.

  在钯（Pd）催化剂的存在下，高炔丙基胺与碘代芳基的单锅反应得以开发，并以高收率或高收率产生了一系列四取代的吡咯衍生物。该过程涉及Sonogashira，分子内加氢胺化，环化和反应的氧化顺序。
• An Efficient Synthesis of Substituted Pyrroles with the Aid of a Low-Valent Titanium Reagent
  作者：Daqing Shi、Chuling Shi、Xiangshan Wang、Qiya Zhuang、Shujiang Tu、Hongwen Hu

  DOI：10.1055/s-2004-831295

  日期：——

  A short and efficient synthesis of substituted pyrroles was accomplished in good yields via the novel coupling cyclization reaction of 1,3-diketones with imines or oximes promoted by TiCl 4 / Zn system.

  通过由 TiCl 4 / Zn 体系促进的 1,3-二酮与亚胺或肟的新型偶联环化反应，以良好的收率完成了取代吡咯的快速有效合成。