5,12,18,21,27,30,36,43-Octabutoxy-2,15,24,33,45,46,47,48-octazaundecacyclo[32.10.1.13,14.116,23.125,32.04,13.06,11.017,22.026,31.035,44.037,42]octatetraconta-1(45),2,4,6,8,10,12,14,16(47),17,19,21,23,25,27,29,31,33,35,37,39,41,43-tricosaene | 191282-57-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 5,12,18,21,27,30,36,43-Octabutoxy-2,15,24,33,45,46,47,48-octazaundecacyclo[32.10.1.13,14.116,23.125,32.04,13.06,11.017,22.026,31.035,44.037,42]octatetraconta-1(45),2,4,6,8,10,12,14,16(47),17,19,21,23,25,27,29,31,33,35,37,39,41,43-tricosaene
• CAS: 191282-57-2
• 化学式: C₇₂H₈₆N₈O₈
• 分子量: 1191.52
• InChiKey: FKJTVBYTMSSSIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.6
• 重原子数：
  88
• 可旋转键数：
  32
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  183
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  5,12,18,21,27,30,36,43-Octabutoxy-2,15,24,33,45,46,47,48-octazaundecacyclo[32.10.1.13,14.116,23.125,32.04,13.06,11.017,22.026,31.035,44.037,42]octatetraconta-1(45),2,4,6,8,10,12,14,16(47),17,19,21,23,25,27,29,31,33,35,37,39,41,43-tricosaene 在 三正丁胺 、 三氯硅烷 作用下， 以 苯 为溶剂， 反应 120.0h， 以47%的产率得到
  参考文献：
  名称：

  Synthesis of a Series of Octabutoxy- and Octabutoxybenzophthalocyanines and Photophysical Properties of Two Members of the Series

  摘要：

  We have developed a new route to silicon-centered phthalocyanines and phthalocyanine-like compounds that is robust and flexible, and of considerable potential usefulness. This route entails insertion of silicon into the metal-free macrocycle. It has been developed in the course of preparing four new and two known metal-free, six new dihydroxysilicon, and six new bis-trihexylsiloxysilicon octabutoxy- and octabutoxybenzophthalocyanines. One of the siloxysilicon compounds, that with the ligand 5,9,12,16,19,23,28,32-octabutoxy-33H,35H-dibenzo[b,g]dinaphtho[2,3-l:2',3'-q]porphyrazine, has a Q-band at a wavelength of 804 nm and an extinction coefficient of 1.9 x 10(5) M-1 cm(-1). Its wavelength thus matches the wavelength of the output of the most common GaAlAs diode laser. The compound and its analog in which the benzo rings are trans to each other instead of cis have no tendency to aggregate in benzene up to a concentration of 150 mu M. The triplet state of the cis isomer has an absorption maximum at 640 nm and a Lifetime in deaerated benzene solution of 105 mu s, while the triplet state of the trans isomer has a maximum at 660 nm and a lifetime of 72 mu s. Both isomers have a triplet quantum yield, Q(t), of ca. 0.20 and a singlet oxygen quantum yield, Q(Delta), of ca. 0.20, photochemical properties that are consistent with potentially efficient photosensitization action in photodynamic therapy of tumors. For both sensitizers, energy transfer from the sensitizer triplet to ground state of dioxygen is reversible at appropriate concentrations. For the cis isomer, the equilibrium constant for the energy transfer process, K-e, is 0.012 +/- 0.001, and the triplet state energy calculated from this, E-T, is 21.29 kcal/mol (E-T derived from phosphorescence measurements is 21.26 kcal/mol). For the trans isomer, K-e, is 3.68 x 10(-3) and E-T is 19.27 kcal/mol.

  DOI：

  10.1021/ja963702q
• 作为产物：
  描述：

  3,6-二丁氧基-1,2-苯二甲腈 在 lithium 、 1,4-二丁氧基-2,3-萘二甲腈 作用下， 以 正丁醇 为溶剂， 反应 1.0h， 以102 mg的产率得到5,8,14,17,23,26,32,39-Octabutoxy-2,11,20,29,41,42,43,44-octazadecacyclo[28.10.1.13,10.112,19.121,28.04,9.013,18.022,27.031,40.033,38]tetratetraconta-1,3(44),4,6,8,10,12,14,16,18,20,22,24,26,28(42),29,31,33,35,37,39-henicosaene
  参考文献：
  名称：

  Synthesis of a Series of Octabutoxy- and Octabutoxybenzophthalocyanines and Photophysical Properties of Two Members of the Series

  摘要：

  We have developed a new route to silicon-centered phthalocyanines and phthalocyanine-like compounds that is robust and flexible, and of considerable potential usefulness. This route entails insertion of silicon into the metal-free macrocycle. It has been developed in the course of preparing four new and two known metal-free, six new dihydroxysilicon, and six new bis-trihexylsiloxysilicon octabutoxy- and octabutoxybenzophthalocyanines. One of the siloxysilicon compounds, that with the ligand 5,9,12,16,19,23,28,32-octabutoxy-33H,35H-dibenzo[b,g]dinaphtho[2,3-l:2',3'-q]porphyrazine, has a Q-band at a wavelength of 804 nm and an extinction coefficient of 1.9 x 10(5) M-1 cm(-1). Its wavelength thus matches the wavelength of the output of the most common GaAlAs diode laser. The compound and its analog in which the benzo rings are trans to each other instead of cis have no tendency to aggregate in benzene up to a concentration of 150 mu M. The triplet state of the cis isomer has an absorption maximum at 640 nm and a Lifetime in deaerated benzene solution of 105 mu s, while the triplet state of the trans isomer has a maximum at 660 nm and a lifetime of 72 mu s. Both isomers have a triplet quantum yield, Q(t), of ca. 0.20 and a singlet oxygen quantum yield, Q(Delta), of ca. 0.20, photochemical properties that are consistent with potentially efficient photosensitization action in photodynamic therapy of tumors. For both sensitizers, energy transfer from the sensitizer triplet to ground state of dioxygen is reversible at appropriate concentrations. For the cis isomer, the equilibrium constant for the energy transfer process, K-e, is 0.012 +/- 0.001, and the triplet state energy calculated from this, E-T, is 21.29 kcal/mol (E-T derived from phosphorescence measurements is 21.26 kcal/mol). For the trans isomer, K-e, is 3.68 x 10(-3) and E-T is 19.27 kcal/mol.

  DOI：

  10.1021/ja963702q