2,5-bis[(4-tert-butylphenyl)(hydroxy)methyl]thiophene | 849346-73-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,5-bis[(4-tert-butylphenyl)(hydroxy)methyl]thiophene
• 英文别名: 2,5-bis[1-(4-tertbutylphenyl)-1-hydroxymethyl]thiophene；2,5-bis(p-tert-butylphenylhydroxymethyl) thiophene；(4-Tert-butylphenyl)-[5-[(4-tert-butylphenyl)-hydroxymethyl]thiophen-2-yl]methanol
• CAS: 849346-73-2
• 化学式: C₂₆H₃₂O₂S
• 分子量: 408.605
• InChiKey: GZHCJODJRDXGGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  68.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-bis[(4-tert-butylphenyl)(hydroxy)methyl]thiophene 在 三溴化硼 、 四氯苯醌 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 5,20-bis(4-tert-butylphenyl)-10,15-bis(4-hydroxyphenyl)-21,23-dithiaporphyrin
  参考文献：
  名称：

  Core-modified porphyrins. Part 4: Steric effects on photophysical and biological properties in vitro

  摘要：

  21,23-Dithiaporphyrins (2-10) were designed and prepared as analogues of 5,20-diphenyl-10,15-bis(4-carboxylatomethoxy)phenyl-21,23-dithiaporphyrin (1) to examine the impact of steric bulk at the 5- and 20-meso positions as well as the impact of symmetry. Changes at the meso positions had minimal impact on the UV-vis-near-IR absorption spectra, quantum yields for the generation of singlet oxygen, and quantum yields for fluorescence and some impact on values of the octanol/water partition coefficient. Of the compounds 1-10, 5-phenyl-20-(2-thienyl)-10,15-bis-(4-carboxylatomethoxy-phenyl)-21,23-dithiaporphyrin (3) showed the greatest phototoxicity toward cultured R3230AC cells, with 68% cell kill at 1 x 10(-7) M and irradiation with 5 J cm(-2) of 350-750 nm light. Results in this study suggest that smaller substituents on the meso ring and less symmetrical compounds are more effective as photosensitizers than compounds with two bulky substituents at adjoining meso sites and a higher symmetry. The mitochondria appear to be involved in the process of phototoxicity as determined by the inhibition of whole cell cytochrome c oxidase activity in cells treated with 3 and light. No impact upon mitochondrial cytochrome c oxidase activity was observed in cells treated with 3 and no light. Fluorescence microscopy studies suggest that the mitochondria are not initial sites of accumulation of 3. (c) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.048
• 作为产物：
  描述：

  噻吩 、 对叔丁基苯甲醛 在 正丁基锂 、 四甲基乙二胺 作用下， 以 正己烷 、 四氢呋喃 为溶剂， 反应 1.0h， 以76%的产率得到2,5-bis[(4-tert-butylphenyl)(hydroxy)methyl]thiophene
  参考文献：
  名称：

  Core-modified porphyrins. Part 4: Steric effects on photophysical and biological properties in vitro

  摘要：

  21,23-Dithiaporphyrins (2-10) were designed and prepared as analogues of 5,20-diphenyl-10,15-bis(4-carboxylatomethoxy)phenyl-21,23-dithiaporphyrin (1) to examine the impact of steric bulk at the 5- and 20-meso positions as well as the impact of symmetry. Changes at the meso positions had minimal impact on the UV-vis-near-IR absorption spectra, quantum yields for the generation of singlet oxygen, and quantum yields for fluorescence and some impact on values of the octanol/water partition coefficient. Of the compounds 1-10, 5-phenyl-20-(2-thienyl)-10,15-bis-(4-carboxylatomethoxy-phenyl)-21,23-dithiaporphyrin (3) showed the greatest phototoxicity toward cultured R3230AC cells, with 68% cell kill at 1 x 10(-7) M and irradiation with 5 J cm(-2) of 350-750 nm light. Results in this study suggest that smaller substituents on the meso ring and less symmetrical compounds are more effective as photosensitizers than compounds with two bulky substituents at adjoining meso sites and a higher symmetry. The mitochondria appear to be involved in the process of phototoxicity as determined by the inhibition of whole cell cytochrome c oxidase activity in cells treated with 3 and light. No impact upon mitochondrial cytochrome c oxidase activity was observed in cells treated with 3 and no light. Fluorescence microscopy studies suggest that the mitochondria are not initial sites of accumulation of 3. (c) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.048

文献信息

• 一种meso位对叔丁基苯基双菲环共轭杂环卟啉衍生物及其制备方法
  申请人：南京林业大学

  公开号：CN105481882A

  公开（公告）日：2016-04-13

  本发明公开了一种含有对叔丁基苯基及菲环基团的杂环卟啉类化合物的结构及其制备方法。以2，5-二羟基衍生物及菲环共轭吡咯为原料，在无水无氧及避光条件下，2，5-二羟基衍生物和菲环共轭吡咯在三氟化硼乙醚催化作用下并经DDQ氧化一步反应生成双菲环共轭杂环卟啉化合物。该制备方法具有反应步骤简单、反应时间短、选择性好、得率高等优点。
• Highly efficient synthesis of 21-thia-5,10,15,20-tetraarylporphyrins and 21,23-dithia-5,10,15,20-tetraarylporphyrins in presence of acidic ionic liquid catalyst
  作者：Amit Kumar Rawat、Soumee Bhattacharya、S.M.S. Chauhan

  DOI：10.1016/j.tetlet.2014.05.005

  日期：2014.8

  The reaction of 2,5-bis-(alpha-arylhydroxymethyl)thiophenes with 5-aryldipyrromethanes in the presence of acidic ionic liquid gives 21-thia-5,10,15,20-tetraarylporphyrins in 30% yield whereas the reaction of 2,5-bis-(alpha-arylhydroxymethyl)thiophenes with 5,10-diaryltripyrromethane or pyrrole gives 21,23-dithia-5,10,15,20-tetraarylporphyrins in 35% yield. Acidic ionic liquids are better catalyst and reaction media than acid catalysed reaction in organic solvents for the synthesis of core modified porphyrins. (C) 2014 Published by Elsevier Ltd.