1-(1,3-Dithiacyclohex-2-yl)-8-formylbiphenylene | 161810-43-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(1,3-Dithiacyclohex-2-yl)-8-formylbiphenylene
• 英文别名: 8-(1,3-Dithian-2-yl)biphenylene-1-carbaldehyde
• CAS: 161810-43-1
• 化学式: C₁₇H₁₄OS₂
• 分子量: 298.43
• InChiKey: YLOPOKOAKVXXOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  吡咯 、 苯甲醛 、 1-(1,3-Dithiacyclohex-2-yl)-8-formylbiphenylene 在 三氟化硼乙醚 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 (5Z,10Z,14Z,19Z)-5-(8-[1,3]Dithian-2-yl-biphenylen-1-yl)-10,15,20-triphenyl-porphyrin
  参考文献：
  名称：

  Facile Synthesis of meso-Tetraaryl Cofacial Diporphyrins

  摘要：

  Metalated derivatives of cofacial diporphyrin ligands have been employed in the binding and catalytic multielectron redox transformations of small molecules. To date, the syntheses of these interesting molecules have been extremely cumbersome and low yielding. In addition, their synthetic methodologies have presented no convenient way to modify the electronic and structural properties of the constituent porphyrins. Here, we report a new method for the synthesis of a family of cofacial diporphyrin ligands in which the two porphyrins are attached via one rigid aromatic linker. The synthesis is considerably shorter-three steps from a suitable dialdehyde bridge-utilizes inexpensive, commercially available reagents, results in markedly increased yields, and allows for convenient variation of the constituent porphyrins. The method involves the monoprotection of a dialdehyde using 1,3-propanedithiol. The monoprotected aldehyde is then cocondensed under modified Lindsey conditions with pyrrole and the aromatic aldehyde of choice. The aldehyde of the resulting species is subsequently deprotected using DDQ and BF3 . O(Et)(2)-a new method for cleavage of dithiane protecting groups. A second Lindsey condensation results in formation of the cofacial diporphyrin ligand. Employing this method, we have synthesized a wide variety of cofacial hetero- and homodiporphyrin ligands, the metalated derivatives of which are currently under investigation in our laboratories.

  DOI：

  10.1021/jo00112a008
• 作为产物：
  描述：

  1,3-丙二硫醇 、 1,8-biphenylenedicarboxaldehyde 在 三氟化硼乙醚 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 以48%的产率得到1-(1,3-Dithiacyclohex-2-yl)-8-formylbiphenylene
  参考文献：
  名称：

  Facile Synthesis of meso-Tetraaryl Cofacial Diporphyrins

  摘要：

  Metalated derivatives of cofacial diporphyrin ligands have been employed in the binding and catalytic multielectron redox transformations of small molecules. To date, the syntheses of these interesting molecules have been extremely cumbersome and low yielding. In addition, their synthetic methodologies have presented no convenient way to modify the electronic and structural properties of the constituent porphyrins. Here, we report a new method for the synthesis of a family of cofacial diporphyrin ligands in which the two porphyrins are attached via one rigid aromatic linker. The synthesis is considerably shorter-three steps from a suitable dialdehyde bridge-utilizes inexpensive, commercially available reagents, results in markedly increased yields, and allows for convenient variation of the constituent porphyrins. The method involves the monoprotection of a dialdehyde using 1,3-propanedithiol. The monoprotected aldehyde is then cocondensed under modified Lindsey conditions with pyrrole and the aromatic aldehyde of choice. The aldehyde of the resulting species is subsequently deprotected using DDQ and BF3 . O(Et)(2)-a new method for cleavage of dithiane protecting groups. A second Lindsey condensation results in formation of the cofacial diporphyrin ligand. Employing this method, we have synthesized a wide variety of cofacial hetero- and homodiporphyrin ligands, the metalated derivatives of which are currently under investigation in our laboratories.

  DOI：

  10.1021/jo00112a008

文献信息

• Facile Synthesis of meso-Tetraaryl Cofacial Diporphyrins
  作者：James P. Collman、David A. Tyvoll、Leng Leng Chng、H. T. Fish

  DOI：10.1021/jo00112a008

  日期：1995.4

  Metalated derivatives of cofacial diporphyrin ligands have been employed in the binding and catalytic multielectron redox transformations of small molecules. To date, the syntheses of these interesting molecules have been extremely cumbersome and low yielding. In addition, their synthetic methodologies have presented no convenient way to modify the electronic and structural properties of the constituent porphyrins. Here, we report a new method for the synthesis of a family of cofacial diporphyrin ligands in which the two porphyrins are attached via one rigid aromatic linker. The synthesis is considerably shorter-three steps from a suitable dialdehyde bridge-utilizes inexpensive, commercially available reagents, results in markedly increased yields, and allows for convenient variation of the constituent porphyrins. The method involves the monoprotection of a dialdehyde using 1,3-propanedithiol. The monoprotected aldehyde is then cocondensed under modified Lindsey conditions with pyrrole and the aromatic aldehyde of choice. The aldehyde of the resulting species is subsequently deprotected using DDQ and BF3 . O(Et)(2)-a new method for cleavage of dithiane protecting groups. A second Lindsey condensation results in formation of the cofacial diporphyrin ligand. Employing this method, we have synthesized a wide variety of cofacial hetero- and homodiporphyrin ligands, the metalated derivatives of which are currently under investigation in our laboratories.