2-(p-acetylphenyl)-5-ethylthiophene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(p-acetylphenyl)-5-ethylthiophene
• 英文别名: 1-[4-(5-Ethylthiophen-2-yl)phenyl]ethanone；1-[4-(5-ethylthiophen-2-yl)phenyl]ethanone
• 化学式: C₁₄H₁₄OS
• 分子量: 230.331
• InChiKey: ITCPRMZZRHTYAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-乙基噻吩 、 4-碘代苯乙酮 在 RhCl(CO){P[OCH(CF₃)₂]₃}₂ 乙二醇二甲醚 、 silver carbonate 作用下， 以 xylene 为溶剂， 反应 0.5h， 以79%的产率得到2-(p-acetylphenyl)-5-ethylthiophene
  参考文献：
  名称：

  Direct C−H Arylation of (Hetero)arenes with Aryl Iodides via Rhodium Catalysis

  摘要：

  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.

  DOI：

  10.1021/ja064500p

文献信息

• Selective β-Arylation of Thiophenes with Aryl Iodides Catalyzed by Dinuclear Palladium Carboxylate Complexes
  作者：Yohei Maki、Takahiro Goto、Naofumi Tsukada

  DOI：10.1002/cctc.201501132

  日期：2016.2

  Novel dinuclear palladium complexes bearing acetoxy ligands were synthesized and characterized by X‐ray crystal analysis. The complexes were utilized for the arylation of 2‐ethylthiophene with iodobenzene to give ethylphenylthiophenes with high β selectivity. The β‐arylation was also applied to a variety of iodoarenes and thiophenes, except those bearing conjugated carbonyl substituents.

  合成了带有乙酰氧基配体的新型双核钯配合物，并通过X射线晶体分析对其进行了表征。该络合物用于2-乙基噻吩与碘苯的芳基化，从而获得具有高β选择性的乙基苯基噻吩。除带有共轭羰基取代基的那些以外，β-芳基化还适用于各种碘代芳烃和噻吩。
• 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.