2-(4-nitrophenyl)-1-phenylpyrrole | 1198351-40-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-(4-nitrophenyl)-1-phenylpyrrole
• CAS: 1198351-40-4
• 化学式: C₁₆H₁₂N₂O₂
• 分子量: 264.283
• InChiKey: QXDKTTJLZLCUAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-(4-nitrophenyl)-2-phenyl-3,6-dihydro-2H-[1,2]oxazine 在 copper nanoparticles on activated carbon 作用下， 反应 6.0h， 以77%的产率得到2-(4-nitrophenyl)-1-phenylpyrrole
  参考文献：
  名称：

  3,6-二氢-1,2-恶嗪合成铜催化的吡咯

  摘要：

  可以在纯净的加热条件下，使用非均相的碳载铜（Cu / C），从3,6-二氢-1,2-恶嗪有效地合成高度官能化的吡咯。此外，原位形成的3,6-二氢-1,2-恶嗪经由亚硝基的亲二烯体和1,3-二烯和以下的Cu / C催化的吡咯合成还提供了相应的吡咯衍生物之间的杂Diels-Alder反应以一锅的方式。

  DOI：

  10.1039/c8gc01373j

文献信息

• β-Selective C–H Arylation of Pyrroles Leading to Concise Syntheses of Lamellarins C and I
  作者：Kirika Ueda、Kazuma Amaike、Richard M. Maceiczyk、Kenichiro Itami、Junichiro Yamaguchi

  DOI：10.1021/ja508449y

  日期：2014.9.24

  The first general β-selective C-H arylation of pyrroles has been developed by using a rhodium catalyst. This C-H arylation reaction, which is retrosynthetically straightforward but results in unusual regioselectivity, could result in de novo syntheses of pyrrole-derived natural products and pharmaceuticals. As such, we have successfully synthesized polycyclic marine pyrrole alkaloids, lamellarins C

  吡咯的第一个通用 β 选择性 CH 芳基化已通过使用铑催化剂开发。这种 CH 芳基化反应在逆向合成上很简单，但会产生不寻常的区域选择性，可以从头合成吡咯衍生的天然产物和药物。因此，我们通过使用吡咯与芳基碘化物的这种β-选择性芳基化（CH / Cl 偶联）和新的双 CH / CH 偶联作为关键步骤，成功合成了多环海洋吡咯生物碱、层状菌素 C 和 I。
• Eco-Friendly Solvents for Palladium-Catalyzed Desulfitative CH Bond Arylation of Heteroarenes
  作者：Anoir Hfaiedh、Kedong Yuan、Hamed Ben Ammar、Bechir Ben Hassine、Jean-François Soulé、Henri Doucet

  DOI：10.1002/cssc.201403429

  日期：2015.5.22

  Herein, we report the Pd‐catalyzed regioselective direct arylation of heteroarenes in which benzenesulfonyl chlorides are used as coupling partners through a desulfitative cross‐coupling that can be performed in diethyl carbonate (DEC) or cyclopentyl methyl ether (CPME) as green and renewable solvents or even in neat conditions instead of dioxane or dimethylacetamide (DMA). Under these solvent conditions

  本文中，我们报道了杂芳烃在钯催化的区域选择性直接芳基化反应中的应用，其中苯磺酰氯通过脱硫交叉偶联作用作为偶联伙伴，可在碳酸二乙酯（DEC）或环戊基甲基醚（CPME）中作为绿色和可再生溶剂进行甚至在纯净的条件下代替二恶烷或二甲基乙酰胺（DMA）。在这些溶剂条件下，反应与各种各样的杂芳烃进行。C2或C5芳基化产物是由呋喃和吡咯衍生物制得的。苯并呋喃还可以在C2位置进行芳基选择性芳基化，而如果使用噻吩和苯并噻吩，则反应会在C3或C4位置选择性地进行。此外，在某些情况下，尤其是对于1-甲基吲哚，
• Palladium-Catalysed Direct Desulfitative Arylation of Pyrroles using Benzenesulfonyl Chlorides as Alternative Coupling Partners
  作者：Rongwei Jin、Kedong Yuan、Emmanuelle Chatelain、Jean-François Soulé、Henri Doucet

  DOI：10.1002/adsc.201400736

  日期：2014.12.15

  AbstractThe reactivity of pyrrole derivatives for palladium‐catalysed desulfitative arylation has been investigated. 1‐Methyl‐, 1‐phenyl‐ and 1‐benzylpyrroles were successfully coupled with a variety of benzenesulfonyl chlorides using a phosphine‐free catalyst. Highly regioselective arylations at carbon C2 of pyrroles were observed in all cases. A wide variety of substituents on the benzenesulfonyl derivative was tolerated.It should be noted that even bromo‐ and iodo‐benzenesulfonyl chlorides were successfully coupled with pyrrole derivatives without cleavage of the CBr or CI bonds, allowing further transformations. Surprisingly, with indoles, mixtures of C2‐ and C3‐arylation products were obtained.magnified image
• Palladium-Catalyzed 2-Arylation of Pyrroles
  作者：Daniel T. Gryko、Olena Vakuliuk、Dorota Gryko、Beata Koszarna

  DOI：10.1021/jo902124c

  日期：2009.12.18

  A methodology that affords N-alkyl-2-arylpyrroles and N-aryl-2-arylpyrroles via direct coupling from aryl iodides has been developed. After examining various reaction parameters: solvent, ratio of reagents, catalyst, base and additives the optimal conditions for the condensation were identified. Two crucial factors, (a) anhydrous DMSO as solvent and (b) 5 M excess of pyrrole counterpart, were found to strongly influence the reaction outcome. The conditions identified (PdCl2(PPh3)(2), AgOAc, anhyd DMSO, KF, 100 degrees C, 5 h) resulted in the formation of 2-arylpyrroles in 14-80% yield. Furthermore, the synthesis is compatible with electron-withdrawing and electron-donating groups on the aryl moiety.
• Copper-catalyzed pyrrole synthesis from 3,6-dihydro-1,2-oxazines
  作者：Naoki Yasukawa、Marina Kuwata、Takuya Imai、Yasunari Monguchi、Hironao Sajiki、Yoshinari Sawama

  DOI：10.1039/c8gc01373j

  日期：——

  Highly-functionalized pyrroles could be effectively synthesized from 3,6-dihydro-1,2-oxazines using a heterogeneous copper on carbon (Cu/C) under neat heating conditions. Furthermore, the in situ formation of 3,6-dihydro-1,2-oxazines via the hetero Diels–Alder reaction between nitroso dienophiles and 1,3-dienes and the following Cu/C-catalyzed pyrrole synthesis also provided the corresponding pyrrole derivatives

  可以在纯净的加热条件下，使用非均相的碳载铜（Cu / C），从3,6-二氢-1,2-恶嗪有效地合成高度官能化的吡咯。此外，原位形成的3,6-二氢-1,2-恶嗪经由亚硝基的亲二烯体和1,3-二烯和以下的Cu / C催化的吡咯合成还提供了相应的吡咯衍生物之间的杂Diels-Alder反应以一锅的方式。