3-(4-acetylphenyl)-1-phenylpyrrole

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-acetylphenyl)-1-phenylpyrrole
• 英文别名: 3-(p-acetylphenyl)-1-phenylpyrrole；1-[4-(1-Phenylpyrrol-3-yl)phenyl]ethanone；1-[4-(1-phenylpyrrol-3-yl)phenyl]ethanone
• 化学式: C₁₈H₁₅NO
• 分子量: 261.323
• InChiKey: VGKCKCDLKAKAII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-苯基吡咯 、 4-碘氰基苯 在 [(P(OCH(CF₃)2)3)2Rh(CO)Cl] silver carbonate 作用下， 以 乙二醇二甲醚 、 间二甲苯 为溶剂， 反应 0.5h， 以58%的产率得到3-(4-acetylphenyl)-1-phenylpyrrole
  参考文献：
  名称：

  Direct coupling of arenes and iodoarenes catalyzed by a rhodium complex with a strongly π-accepting phosphite ligand

  摘要：

  A new rhodium-based catalytic system for the direct C-H coupling of arenes and iodoarenes that shows high activity with reasonably broad scope was developed. Under the catalytic influence of RhCl(CO){P[OCH(CF3)(2)](3)}(2) and Ag2CO3, the direct C-H arylation of heteroarenes and arenes took place with iodoarenes to afford a range of biaryls in good to excellent yields with high regioselectivity. Thiophenes, furans, pyrroles, indoles, and alkoxybenzenes are applicable to this arylation protocol. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.053

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。
• Direct C−H Arylation of (Hetero)arenes with Aryl Iodides via Rhodium Catalysis
  作者：Shuichi Yanagisawa、Tomoko Sudo、Ryoji Noyori、Kenichiro Itami

  DOI：10.1021/ja064500p

  日期：2006.9.1

  A new method for the catalytic C-H arylation of heteroarenes and arenes that manifests high activity paired with reasonably broad scope was developed. Under the catalytic influence of RhCl(CO)P[OCH(CF3)2]3}2 and Ag2CO3, the direct C-H arylation of heteroarenes/arenes with aryl/heteroaryl iodides took place to afford a range of biaryls in good to excellent yields with high regioselectivity. Thiophenes, furans, pyrroles, indoles, and alkoxybenzenes are applicable in this arylation protocol.
• Direct coupling of arenes and iodoarenes catalyzed by a rhodium complex with a strongly π-accepting phosphite ligand
  作者：Shuichi Yanagisawa、Tomoko Sudo、Ryoji Noyori、Kenichiro Itami

  DOI：10.1016/j.tet.2008.01.053

  日期：2008.6

  A new rhodium-based catalytic system for the direct C-H coupling of arenes and iodoarenes that shows high activity with reasonably broad scope was developed. Under the catalytic influence of RhCl(CO)P[OCH(CF3)(2)](3)}(2) and Ag2CO3, the direct C-H arylation of heteroarenes and arenes took place with iodoarenes to afford a range of biaryls in good to excellent yields with high regioselectivity. Thiophenes, furans, pyrroles, indoles, and alkoxybenzenes are applicable to this arylation protocol. (C) 2008 Elsevier Ltd. All rights reserved.