3-Phenylsulfanylthiophene-2-carboxylic acid | 81028-81-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-Phenylsulfanylthiophene-2-carboxylic acid
• CAS: 81028-81-1
• 化学式: C₁₁H₈O₂S₂
• 分子量: 236.315
• InChiKey: ZFROJIZBMPKHOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Phenylsulfanylthiophene-2-carboxylic acid 在 三氟甲磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以70%的产率得到9H-thieno[3,2-b]thiochromen-9-one
  参考文献：
  名称：

  Ruthenium(II)-Catalyzed ortho-C–H Chalcogenation of Benzoic Acids via Weak O-Coordination: Synthesis of Chalcogenoxanthones

  摘要：

  A general protocol for direct chalcogenation of inert C-H bonds of (hetero)aromatic carboxylic acids is developed with a ruthenium(II) catalyst using readily available starting materials, offering densely substituted ortho-chalcogenyl aromatic acids in high yields (up to 96%). The strategy avoids the installation of an external directing group, use of metallic oxidants, and features operational simplicity with ample substrate scope. Synthetic application :en route to biologically important chalcogenoxanthones is also demonstrated. This work represents the first example of ruthenium(II)-catalyzed direct C-H chalcogenation of benzoic acids.

  DOI：

  10.1021/acs.orglett.7b00996
• 作为产物：
  描述：

  2-噻吩甲酸 、 二苯二硫醚 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 碳酸氢钠 、 三环己基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 3-Phenylsulfanylthiophene-2-carboxylic acid
  参考文献：
  名称：

  Ruthenium(II)-Catalyzed ortho-C–H Chalcogenation of Benzoic Acids via Weak O-Coordination: Synthesis of Chalcogenoxanthones

  摘要：

  A general protocol for direct chalcogenation of inert C-H bonds of (hetero)aromatic carboxylic acids is developed with a ruthenium(II) catalyst using readily available starting materials, offering densely substituted ortho-chalcogenyl aromatic acids in high yields (up to 96%). The strategy avoids the installation of an external directing group, use of metallic oxidants, and features operational simplicity with ample substrate scope. Synthetic application :en route to biologically important chalcogenoxanthones is also demonstrated. This work represents the first example of ruthenium(II)-catalyzed direct C-H chalcogenation of benzoic acids.

  DOI：

  10.1021/acs.orglett.7b00996

文献信息

• Application of regioselective thiophene lithiation to the synthesis of thiophene analogs of xanthones and thioxanthones
  作者：Jeffrey W. H. Watthey、Mahesh Desai

  DOI：10.1021/jo00348a032

  日期：1982.4
• WATTHEY, J. W. H.;DESAI, M., J. ORG. CHEM., 1982, 47, N 9, 1755-1759
  作者：WATTHEY, J. W. H.、DESAI, M.

  DOI：——

  日期：——
• Ruthenium(II)-Catalyzed <i>ortho</i>-C–H Chalcogenation of Benzoic Acids via Weak O-Coordination: Synthesis of Chalcogenoxanthones
  作者：Anup Mandal、Suman Dana、Harekrishna Sahoo、Gowri Sankar Grandhi、Mahiuddin Baidya

  DOI：10.1021/acs.orglett.7b00996

  日期：2017.5.5

  A general protocol for direct chalcogenation of inert C-H bonds of (hetero)aromatic carboxylic acids is developed with a ruthenium(II) catalyst using readily available starting materials, offering densely substituted ortho-chalcogenyl aromatic acids in high yields (up to 96%). The strategy avoids the installation of an external directing group, use of metallic oxidants, and features operational simplicity with ample substrate scope. Synthetic application :en route to biologically important chalcogenoxanthones is also demonstrated. This work represents the first example of ruthenium(II)-catalyzed direct C-H chalcogenation of benzoic acids.