5-(p-cyanophenyl)-5H-1,3-dithiolo[4,5-c]pyrrol-2-one | 1214754-11-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-(p-cyanophenyl)-5H-1,3-dithiolo[4,5-c]pyrrol-2-one
• 英文别名: 4-(2-Oxo-[1,3]dithiolo[4,5-c]pyrrol-5-yl)benzonitrile
• CAS: 1214754-11-6
• 化学式: C₁₂H₆N₂OS₂
• 分子量: 258.324
• InChiKey: JXGSZKOISWGUML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,5-双(甲硫代)-1,3-二硫杂环戊烯-2-硫酮 、 5-(p-cyanophenyl)-5H-1,3-dithiolo[4,5-c]pyrrol-2-one 在 亚磷酸三乙酯 作用下， 反应 4.5h， 以25%的产率得到2-[4,5-bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-N-p-cyanophenyl-1,3-dithiolo[4,5-c]pyrrole
  参考文献：
  名称：

  N-Aryl Pyrrolo-tetrathiafulvalene Based Ligands: Synthesis and Metal Coordination

  摘要：

  A straight forward general synthetic access to N-aryl-1,3-dithiolo[4,5-c]pyrrole-2-thione derivatives 6 from acetylenedicarbaldehyde monoacetal is depicted. In addition to their potentiality as precursors to dithioalkyl-pyrrole derivatives, thiones 6 are key building blocks to N-aryl monopyrrolotetrathiafulvalene (MPTTF) derivatives 10. X-ray structures of four of these thiones intermediates, reminiscent of the corresponding MPTTF derivatives, are provided. When the aryl group is it binding pyridyl unit, the MPTTF derivative 10a can coordinate M(II) salts (M = Pt, Pd). The first examples of metal-directed orthogonal MPTTF-based dimers 11-14, obtained through coordination of 10a to cis-blocked square planar Pt or Pd complexes are described. Studies on the parameters influencing the dimer construction are presented, as well its first recognition properties of the resulting electron-rich clip for C-60.

  DOI：

  10.1021/jo902529e
• 作为产物：
  描述：

  5-(p-cyanophenyl)-5H-1,3-dithiolo[4,5-c]pyrrole-2-thione 在 mercury(II) diacetate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以54%的产率得到5-(p-cyanophenyl)-5H-1,3-dithiolo[4,5-c]pyrrol-2-one
  参考文献：
  名称：

  N-Aryl Pyrrolo-tetrathiafulvalene Based Ligands: Synthesis and Metal Coordination

  摘要：

  A straight forward general synthetic access to N-aryl-1,3-dithiolo[4,5-c]pyrrole-2-thione derivatives 6 from acetylenedicarbaldehyde monoacetal is depicted. In addition to their potentiality as precursors to dithioalkyl-pyrrole derivatives, thiones 6 are key building blocks to N-aryl monopyrrolotetrathiafulvalene (MPTTF) derivatives 10. X-ray structures of four of these thiones intermediates, reminiscent of the corresponding MPTTF derivatives, are provided. When the aryl group is it binding pyridyl unit, the MPTTF derivative 10a can coordinate M(II) salts (M = Pt, Pd). The first examples of metal-directed orthogonal MPTTF-based dimers 11-14, obtained through coordination of 10a to cis-blocked square planar Pt or Pd complexes are described. Studies on the parameters influencing the dimer construction are presented, as well its first recognition properties of the resulting electron-rich clip for C-60.

  DOI：

  10.1021/jo902529e

文献信息

• <i>N</i>-Aryl Pyrrolo-tetrathiafulvalene Based Ligands: Synthesis and Metal Coordination
  作者：Jean-Yves Balandier、Marcos Chas、Paul I. Dron、Sébastien Goeb、David Canevet、Ahmed Belyasmine、Magali Allain、Marc Sallé

  DOI：10.1021/jo902529e

  日期：2010.3.5

  A straight forward general synthetic access to N-aryl-1,3-dithiolo[4,5-c]pyrrole-2-thione derivatives 6 from acetylenedicarbaldehyde monoacetal is depicted. In addition to their potentiality as precursors to dithioalkyl-pyrrole derivatives, thiones 6 are key building blocks to N-aryl monopyrrolotetrathiafulvalene (MPTTF) derivatives 10. X-ray structures of four of these thiones intermediates, reminiscent of the corresponding MPTTF derivatives, are provided. When the aryl group is it binding pyridyl unit, the MPTTF derivative 10a can coordinate M(II) salts (M = Pt, Pd). The first examples of metal-directed orthogonal MPTTF-based dimers 11-14, obtained through coordination of 10a to cis-blocked square planar Pt or Pd complexes are described. Studies on the parameters influencing the dimer construction are presented, as well its first recognition properties of the resulting electron-rich clip for C-60.