tetrakis-1,2,4,5-benzene | 139086-83-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: tetrakis-1,2,4,5-benzene
• 英文别名: 2-[2-[5-[2,4,5-Tris[5-[2-(1,3-dioxan-2-yl)phenyl]pentyl]phenyl]pentyl]phenyl]-1,3-dioxane
• CAS: 139086-83-2
• 化学式: C₆₆H₈₆O₈
• 分子量: 1007.4
• InChiKey: KAKDZHSKKYYYND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.4
• 重原子数：
  74
• 可旋转键数：
  28
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tetrakis-1,2,4,5-benzene 在 高氯酸 、 2,4-二硝基苯甲醛 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 72.0h， 以60%的产率得到tetrakis-1,2,4,5-benzene
  参考文献：
  名称：

  The synthesis of a porphyrin with a hydrocarbon encapsulated face

  摘要：

  The uniquely hydrocarbon-like capped porphyrin (C70H68N4), 1i, has been successfully prepared by a high dilution reaction of pyrrole with tetrakis-1,2,4,5-[pentyl-5'-(2"-formylphenyl)]-benzene 1h in the presence of boron trifluoride etherate. The aldehyde 1h was prepared by four simultaneous Wittig condensations of a phosphonium salt, 1e, with 1,2,4,5-tetraformylbenzene, followed by reduction of the double bonds with Raney nickel and deprotection with perchloric acid.

  DOI：

  10.1016/s0040-4020(01)96191-5
• 作为产物：
  描述：

  1,2,4,5-苯四甲醛 在 镍 18-冠醚-6 、 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成 tetrakis-1,2,4,5-benzene
  参考文献：
  名称：

  The synthesis of a porphyrin with a hydrocarbon encapsulated face

  摘要：

  The uniquely hydrocarbon-like capped porphyrin (C70H68N4), 1i, has been successfully prepared by a high dilution reaction of pyrrole with tetrakis-1,2,4,5-[pentyl-5'-(2"-formylphenyl)]-benzene 1h in the presence of boron trifluoride etherate. The aldehyde 1h was prepared by four simultaneous Wittig condensations of a phosphonium salt, 1e, with 1,2,4,5-tetraformylbenzene, followed by reduction of the double bonds with Raney nickel and deprotection with perchloric acid.

  DOI：

  10.1016/s0040-4020(01)96191-5

文献信息

• Studies on a hydrocarbon capped free base tetraphenylporphyrin and its conjugate acids - first observation of a monoprotonated tetrapehylporphyrin &{;CapTPP(H3+)CF3CO2−&};
  作者：Örn Almarsson、Andrei Blaskó、Thomas C. Bruice

  DOI：10.1016/s0040-4020(01)80553-6

  日期：1993.1

  H-1-NMR and visible absorbtion spectroscopic titrations of a unique hydrocarbon capped porphyrin 3H-2 with trifluoroacetic acid in chloroform result in the formation of a monoprotonated porphyrin species 3H3+CF3CO2-}. This represents the first observation of a monobasic tetraphenylporphyrin acid. The monocation forms the dibasic 3H42+CF3CO2-}2 upon further addition of acid. Back-titration of 3H42+CF3CO2-}2 with DMSO demonstrates that the monocation can be generated from the diacid as well as the free base porphyrin. The capping structure on one face of the tetraphenylporphyrin is suggested to diminish the extent of solvation of one proton of 3H42+CF3CO2-}2 by CF3CO2-, thereby rendering the first dissociation constant (represented by C50(1)) considerably larger than the second dissociation (C50(2)) F-19 NMR chemical shifts of the counterions at -50-degrees-C show a similarity to the CF3CO2- counterions of TPPH42+CF3CO2-}2 and indicated a strong association with the porphyrin acid species. 2D NMR ROESY spectroscopy with Distance Geometry Refinement afforded a solution structure for 3H-2, from which representative structures of possible inclusion compounds 3H3+CF3CO2-} and 3H2CHCl3} were created by molecular modeling. Although the dome of the capping structure is predicted to be large enough to accommodate a trifluoroacetate anion on the inside, F-19 NMR spectra and FAB-mass spectra do not support the presence of an acid-base inclusion compound.