1,5-dimethyl-2,4-diphenylpyrrole | 15364-06-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1,5-dimethyl-2,4-diphenylpyrrole
• 英文别名: 1,2-dimethyl-3,5-diphenyl-pyrrole；1,2-Dimethyl-3,5-diphenyl-pyrrol；1,2-Dimethyl-3,5-diphenylpyrrol；1,2-Dimethyl-3,5-diphenylpyrrole
• CAS: 15364-06-4
• 化学式: C₁₈H₁₇N
• 分子量: 247.34
• InChiKey: MQMFBAQRSWAFGF-UHFFFAOYSA-N

物化性质

• 熔点：
  155 °C
• 沸点：
  372.7±21.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  1-苯基-1,4-戊二酮 在 双(乙腈)氯化钯(II) 、 氨基磺酸 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 2.08h， 生成 1,5-dimethyl-2,4-diphenylpyrrole
  参考文献：
  名称：

  Palladium-Catalyzed C−H Arylation of 2,5-Substituted Pyrroles

  摘要：

  The palladium-catalyzed direct arylation of 2,5-substituted pyrrole derivatives with diaryliodonium salts to generate tri-, tetra-, and penta-substituted pyrrole products is described. The scope and limitations of these transformations are also reported.

  DOI：

  10.1021/ol102734g

文献信息

• Ring Expansion of 2‐(α‐Hydroxyalkyl)azetidines: A Synthetic Route to Functionalized Pyrrolidines
  作者：François Durrat、Monica Vargas Sanchez、François Couty、Gwilherm Evano、Jérôme Marrot

  DOI：10.1002/ejoc.200800316

  日期：2008.7

  A series of 2-(α-hydroxyalkyl)azetidines synthesized from enantiomerically pure β-amino alcohols and presenting various patterns both on the four-membered ring and on the adjacent hydroxy group were treated with either thionyl chloride or methanesulfonyl chloride in the presence of triethylamine. The thus-prepared 2-(α-chloro- or α-methanesulfonyloxyalkyl)azetidines were shown to rearrange stereospecifically

  在三乙胺存在下，用亚硫酰氯或甲磺酰氯处理由对映体纯 β-氨基醇合成的一系列 2-（α-羟烷基）氮杂环丁烷，并在四元环和相邻羟基上呈现各种模式. 如此制备的 2-(α-氯-或 α-甲磺酰氧基烷基) 氮杂环丁烷显示立体定向重排成 3-(氯-或甲磺酰氧基) 吡咯烷。当这种重排在添加的亲核试剂（NaN3、KCN、KOH 或 NaOAc）存在下进行时，产生的吡咯烷会在 C-3 立体特异性地结合添加的亲核试剂。形成的吡咯烷中取代基的相对构型与中间体双环氮丙啶离子形成的机制一致，它在桥头碳原子上区域选择性地打开。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• 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。
• Croce, Piero Dalla; Rosa, Concetta La, Heterocycles, 1988, vol. 27, # 12, p. 2825 - 2832
  作者：Croce, Piero Dalla、Rosa, Concetta La

  DOI：——

  日期：——
• Nesvadba, Petr; Kuthan, Josef, Collection of Czechoslovak Chemical Communications, 1984, vol. 49, # 2, p. 543 - 548
  作者：Nesvadba, Petr、Kuthan, Josef

  DOI：——

  日期：——
• Palladium-Catalyzed C−H Arylation of 2,5-Substituted Pyrroles
  作者：Anna M. Wagner、Melanie S. Sanford

  DOI：10.1021/ol102734g

  日期：2011.1.21

  The palladium-catalyzed direct arylation of 2,5-substituted pyrrole derivatives with diaryliodonium salts to generate tri-, tetra-, and penta-substituted pyrrole products is described. The scope and limitations of these transformations are also reported.