1-methyl-2,3,5-triphenyl-1H-pyrrole | 13901-77-4

• 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-methyl-2,3,5-triphenyl-1H-pyrrole
• 英文别名: 1-methyl-2,3,5-triphenylpyrrole；N-methyl-2,3,5-triphenyl-pyrrol；1-methyl-2,3,5-triphenyl-pyrrole；1-Methyl-2,3,5-triphenyl-pyrrol
• CAS: 13901-77-4
• 化学式: C₂₃H₁₉N
• 分子量: 309.411
• InChiKey: MDQIJASVFIOQIH-UHFFFAOYSA-N

物化性质

• 熔点：
  177-178 °C(Solv: ethanol (64-17-5))
• 沸点：
  426.6±24.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 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-methyl-2,3,5-triphenyl-1H-pyrrole 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：

  安息香精油 在 potassium cyanide 、 sodium acetate 、 溶剂黄146 作用下， 生成 1-methyl-2,3,5-triphenyl-1H-pyrrole
  参考文献：
  名称：

  Lespagnol et al., Bulletin de la Societe de Pharmacie de Lille, 1955, p. 87

  摘要：

  DOI：

文献信息

• The Reactions of Monoalkylthio- or Monoarylthio-Substituted Cyclopropenium Salt with Nitrogen Nucleophiles: Formation of Polyfunctionally Substituted Pyrroles or Pyrazoles
  作者：Hiroshi Yoshida、Fumitaka Utsumi、Hideki Suzuki、Satoru Ito、Shin-ichi Sakashita、Tsuyoshi Ogata、Kiyoshi Matsumoto

  DOI：10.1246/bcsj.65.698

  日期：1992.3

  The reactions of monoalkylthio- or monoarylthio-substituted cyclopropenium salt (1) with a number of secondary amines were studied. The amines, such as N-methylaniline, yielded indenes, whereas N-alkyl- or N-arylbenzylamines gave 1-alkyl- or 1-aryl-2-phenylpyrroles in low-to-moderate yields, depending on the kinds of substituents of the amines and 1. The reaction with N-isopropylbenzylamine-α,α-d2 (i-PrNHCD2Ph) resulted in the formation of the 1-isopropyl-2,3,5-triphenylpyrrole-4-d, clearly indicating the intramolecular H-abstraction mechanism via vinylcarbene intermediates for the formation of pyrroles. The reaction of 1 with tosylhydrazones afforded the ring opend hydrazide, while with phenyl-, methyl-, and t-butylhydrazines gave 1,4,5-trisubstituted pyrazoles in small yields.

  研究了单烷基硫或单芳基硫取代的环丙烯盐（1）与多种二级胺的反应。诸如N-甲基苯胺等胺类，产生了茚，并且N-烷基或N-芳基苯基胺则根据胺和1的取代基的种类，产生了低至中等产率的1-烷基或1-芳基-2-苯基吡咯。与N-异丙基苯基胺-α,α-d2（i-PrNHCD2Ph）的反应生成了1-异丙基-2,3,5-三苯基吡咯-4-d，清楚地表明通过乙烯基卡宾中间体形成吡咯的分子内氢抽取机制。1与对甲基肼的反应生成了环打开的肼，另一方面，与苯基、甲基和叔丁基肼的反应则产生了小产率的1,4,5-三取代吡唑。
• Catalytic Multicomponent Synthesis of Highly Substituted Pyrroles Utilizing a One-Pot Sila-Stetter/Paal−Knorr Strategy
  作者：Ashwin R. Bharadwaj、Karl A. Scheidt

  DOI：10.1021/ol049044t

  日期：2004.7.1

  [reaction: see text] A multicomponent synthesis of highly substituted pyrroles catalyzed by thiazolium salts has been disclosed. The reaction employs an acyl anion conjugate addition reaction of acylsilanes (sila-Stetter) and unsaturated ketones to generate 1,4-dicarbonyl compounds in situ. The subsequent addition of various amines promotes a Paal-Knorr reaction, affording the desired pyrrole nucleus

  [反应：见正文]已经公开了由噻唑鎓盐催化的高度取代的吡咯的多组分合成。该反应采用酰基硅烷（sila-Stetter）和不饱和酮的酰基阴离子共轭加成反应，以原位生成1,4-二羰基化合物。随后加入各种胺促进了Paal-Knorr反应，以有效的一锅法提供了所需的吡咯核。
• Thiazolium-Catalyzed Additions of Acylsilanes:  A General Strategy for Acyl Anion Addition Reactions
  作者：Anita E. Mattson、Ashwin R. Bharadwaj、Andrea M. Zuhl、Karl A. Scheidt

  DOI：10.1021/jo060699c

  日期：2006.7.1

  utilizing N-heterocyclic carbenes (NHCs) derived from thiazolium salts has been developed for the generation of carbonyl anions from acylsilanes. Synthetically useful 1,4-diketones and N-phosphinoyl-α-aminoketones have been prepared in good to excellent yields via NHC-catalyzed additions of acylsilanes to the corresponding α,β-unsaturated systems and N-phosphinoylimines. These organocatalytic reactions

  已经开发出一种利用衍生自噻唑鎓盐的N-杂环卡宾（NHC）的策略，用于从酰基硅烷生成羰基阴离子。合成有用的1,4-二酮和N-膦酰基-α-氨基酮是通过NHC催化将酰基硅烷添加到相应的α，β-不饱和体系和N中来制备的，具有良好至优异的收率-膦基嘧啶。这些有机催化反应是耐空气和耐水的方法，可进行稳健的羰基阴离子加成反应。另外，已经使用该羰基阴离子方法以一锅法有效地合成了多取代的芳族呋喃和吡咯。向反应中加入醇使该过程在噻唑鎓盐中具有催化作用。为了沿着提出的反应途径合成潜在的中间体，已经确定甲硅烷基化的噻唑鎓甲醇在适当的亲电试剂存在下经受标准反应条件时可以提供高收率的羰基阴离子加成产物。
• Synthesis of Pyrroles from 1-Dialkylamino-3-phosphoryl(or phosphanyl)allenes through 1,5-Cyclization of Conjugated Azomethine Ylide Intermediates
  作者：Martin Reisser、Gerhard Maas

  DOI：10.1021/jo049586o

  日期：2004.7.1

  5-diarylpyrroles 6a−f and [a]-annulated benzo[c]azepines 7a,b,d. These transformations are likely to include conjugated azomethine ylide intermediates that can undergo either a 1,5- or a 1,7-electrocyclization. The periselectivity is markedly shifted toward 1,5-cyclization when the diphenylphosphanyl substituent is replaced by the diphenylphosphoryl group. Thus, 1-dialkylamino-3-(diphenylphosphoryl)allenes

  1-二烷基氨基-1,3-二芳基-3- diphenylphosphanylallenes 3A - ë被热转化成一个-annulated 3,5- diarylpyrroles 6A - ˚F和[一个] -annulated苯并[ C ^ ]氮杂7A，b，d。这些转化可能包括可以进行1,5-或1,7-电环化的共轭甲亚胺叶立德中间体。当二苯基膦烷基取代基被二苯基磷酰基取代时，周选择性显着转向1，5-环化。因此，1 -二烷基氨基-3-（二苯基磷酰基）丙二烯4A - ˚F收率吡咯6个，并用改进的产量，除非在丙二烯的3-芳基取代基是富电子太（例如，苯并二氧戊环-5-基，4F → 7F）。可以通过一锅法进行三步或四步氨基丙烯4的制备和热转化，从而提供了从烯胺酮方便地合成[ a ]-环化的3,5-二芳基吡咯的方法。
• “One pot” regiospecific synthesis of polysubstituted pyrroles from benzylamines and ynones under metal free conditions
  作者：Jinhai Shen、Guolin Cheng、Xiuling Cui

  DOI：10.1039/c3cc43844a

  日期：——

  A convenient “one-pot” weak base-promoted synthesis of polysubstituted pyrroles has been developed from benzylamines and ynones. This transformation involves the Michael addition reaction and intramolecular condensation, which features high regioselectivity, high efficiency, environmental friendliness and metal free. A series of polysubstituted pyrroles were provided in up to 91% yield for 27 examples.

  以苄胺和炔酮为原料，开发了一种简便的 "一锅 "弱碱促进的多取代吡咯合成方法。该转化过程包括迈克尔加成反应和分子内缩合反应，具有高区域选择性、高效、环保和无金属等特点。在 27 个实例中，提供了一系列多取代吡咯，收率高达 91%。