2-formyl-3-(o-nitrophenyl)-1-tosylpyrrole | 233770-18-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-formyl-3-(o-nitrophenyl)-1-tosylpyrrole
• 英文别名: 1-(4-Methylphenyl)sulfonyl-3-(2-nitrophenyl)pyrrole-2-carbaldehyde
• CAS: 233770-18-8
• 化学式: C₁₈H₁₄N₂O₅S
• 分子量: 370.386
• InChiKey: HCVLOVXCQRPQRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-formyl-3-(o-nitrophenyl)-1-tosylpyrrole 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 以82%的产率得到2-Formyl-3-(2'-nitrophenyl)-pyrrol
  参考文献：
  名称：

  A general synthesis of 2-formyl-3-arylpyrroles

  摘要：

  2-Formyl-3-iodo-1 -tosylpyrrole 2 has been prepared in four steps from cinnamaldehyde. It was coupled with a wide variety of arylboronic acids to give the corresponding biaryl compounds in high yields. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00808-4
• 作为产物：
  描述：

  苯磺酰胺,4-甲基-N-(3-苯基-2-亚丙烯基)-,(E,E)- 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 barium dihydroxide 、 potassium permanganate 、 正丁基锂 、 氢碘酸 、 zinc(II) chloride 作用下， 以 乙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.08h， 生成 2-formyl-3-(o-nitrophenyl)-1-tosylpyrrole
  参考文献：
  名称：

  A general synthesis of 2-formyl-3-arylpyrroles

  摘要：

  2-Formyl-3-iodo-1 -tosylpyrrole 2 has been prepared in four steps from cinnamaldehyde. It was coupled with a wide variety of arylboronic acids to give the corresponding biaryl compounds in high yields. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00808-4

文献信息

• Total Syntheses of the 3<i>H</i>-Pyrrolo[2,3-<i>c</i>]quinolone-Containing Alkaloids Marinoquinolines A–F, K, and Aplidiopsamine A Using a Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Pathway
  作者：Benoit Bolte、Christopher S. Bryan、Phillip P. Sharp、Soheil Sayyahi、Charly Rihouey、Amy Kendrick、Ping Lan、Martin G. Banwell、Colin J. Jackson、Nicholas J. Fraser、Anthony C. Willis、Jas S. Ward

  DOI：10.1021/acs.joc.9b02725

  日期：2020.1.17

  of the marinoquinoline family of natural products, together with the related marine alkaloid aplidiopsamine A (12), have been synthesized using various combinations of palladium-catalyzed Ullmann cross-coupling and reductive cyclization processes involving a C3-arylated pyrrole as the common intermediate. These natural products have been characterized by single-crystal X-ray analyses and evaluated as

  使用钯催化的Ullmann交叉偶联和涉及C3的还原环化过程的各种组合合成了代表天然产物马来喹啉家族主要成员的化合物1-6和11，以及相关的海洋生物碱Aplidiopsamine A（12）。 -芳基吡咯为常见中间体。这些天然产物已通过单晶X射线分析进行了表征，并被评估为乙酰胆碱酯酶（AChE）的抑制剂，同类物2被证明是活性最高的。
• Studies of palladium-catalyzed coupling reactions for preparation of hindered 3-arylpyrroles relevant to (-)-rhazinilam and its analogues
  作者：Léon Ghosez、Cécile Franc、Frédéric Denonne、Claire Cuisinier、Roland Touillaux

  DOI：10.1139/v01-156

  日期：2001.11.1

  Suzuki cross-coupling reactions of 3-pyrroleboronic acid derivatives with haloaromatics and the reverse process i.e., the coupling of 3-iodo(bromo)pyrroles with arylboronic acids have been investigated as a potential key step in the synthesis of (–)-rhazinilam and analogues. It was found that 3-iodo-2-formyl-1-tosylpyrroles efficiently coupled with a variety of arylboronic acids in the presence of PdCl₂(dppf) as catalyst. This catalytic system is compatible with a broad spectrum of arylboronic acids — electron-rich, electron-poor, hindered, heterocyclic — which easily coupled with the pyrrole substrate.Key words: 2-substituted-3-arylpyrroles, biaryls, coupling reactions, arylboronic acids, palladium coupling, catalysis.

  铜促进3-吡咯硼酸衍生物与卤代芳香烃的Suzuki交叉偶联反应，以及反向过程即3-碘(溴)吡咯烷与芳基硼酸的偶联反应已被研究作为合成(–)-拉洁嗪和类似物的潜在关键步骤。发现3-碘-2-甲酰基-1-对甲苯磺酰基吡咯烷在PdCl₂(dppf)催化剂存在下有效地与各种芳基硼酸偶联。该催化系统与广泛的芳基硼酸兼容，包括富电子、贫电子、障碍、杂环化合物，这些都可以轻松地与吡咯底物偶联。关键词：2-取代-3-芳基吡咯、联苯、偶联反应、芳基硼酸、钯偶联、催化。
• A general synthesis of 2-formyl-3-arylpyrroles
  作者：Cécile Franc、Frédéric Denonne、Claire Cuisinier、Léon Ghose

  DOI：10.1016/s0040-4039(99)00808-4

  日期：1999.6

  2-Formyl-3-iodo-1 -tosylpyrrole 2 has been prepared in four steps from cinnamaldehyde. It was coupled with a wide variety of arylboronic acids to give the corresponding biaryl compounds in high yields. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.