2,5-bis[(2-thienyl)hydroxymethyl]thiophene | 645420-42-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2,5-bis[(2-thienyl)hydroxymethyl]thiophene
• 英文别名: 2,5-bis[2-thienyl(hydroxy)methyl]thiophene；thiophene-2,5-diylbis(thien-2-ylmethanol)；[5-[Hydroxy(thiophen-2-yl)methyl]thiophen-2-yl]-thiophen-2-ylmethanol
• CAS: 645420-42-4
• 化学式: C₁₄H₁₂O₂S₃
• 分子量: 308.446
• InChiKey: UOAJMHPLSHDKGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-bis[(2-thienyl)hydroxymethyl]thiophene 在 三氟化硼乙醚 、 三溴化硼 、 四氯苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 5,20-bis(2-thienyl)-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 、 2-噻吩甲醛 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80%的产率得到2,5-bis[(2-thienyl)hydroxymethyl]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

• Synthesis and Structural Characterization ofmeso-Thienyl Core-Modified Porphyrins
  作者：Iti Gupta、C.-Hsiung Hung、Mangalampalli Ravikanth

  DOI：10.1002/ejoc.200300228

  日期：2003.11

  A series of meso-thienyl-substituted porphyrins with different porphyrin cores such as N3S, N2S2 and N3O were synthesized and characterized. The thienyl groups at the meso-carbon atoms change the electronic properties of the porphyrin ring. The X-ray structure solved for the N2S2 porphyrin with four meso-thienyl groups showed supramolecular assembly formation in the solid state due to C−H···N hydrogen

  合成并表征了一系列具有不同卟啉核心如 N3S、N2S2 和 N3O 的内消旋噻吩基取代的卟啉。中间碳原子上的噻吩基改变了卟啉环的电子特性。具有四个中噻吩基的 N2S2 卟啉的 X 射线结构显示出固态超分子组装形成，这是由于一个卟啉环的中噻吩基的 CH 基团与另一个卟啉环的吡咯N原子。具有两个内消旋噻吩基和两个内消旋芳基的 N3S 卟啉的 X 射线分析没有显示任何超分子组装在固态下的形成。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Core-Modified Analogues of Expanded Porphyrins Containing Rigid β,β′-Linked<i>o</i>-Phenylene Bridges
  作者：Vijayendra S. Shetti、Se-Young Kee、Chang-Hee Lee

  DOI：10.1002/asia.201301320

  日期：2014.3

  ring other than pyrrole and rigid β‐β′ linkages have not been well studied up to date. The rigidity caused by the conformational restriction would change the spectroscopic properties of the system as compared with those of the normal congeners. With these considerations, we have synthesized and fully characterized π‐extended, core modified expanded porphyrins bearing rigid bipyrrole units. Core‐modified

  迄今为止，尚未对结构修饰导致包含除吡咯和刚性β-β'键以外的杂环的π-延伸的芳香族大环的形成进行研究。与常规同类物相比，由构象限制引起的刚性将改变系统的光谱性质。考虑到这些因素，我们合成并表征了带有刚性联吡咯单元的π扩展核修饰膨胀卟啉。通过路易斯酸催化的萘联吡咯与噻吩/呋喃二醇的缩合反应合成了核修饰的萘并呋喃酮，而萘并二萘嵌苯醚是通过在温和的反应条件下使2,9-二甲酰基-萘并吡咯与16-噻吩/草酰三吡喃反应制得的。萘鲁比林和萘草皮苷的核心修饰类似物均表现出芳香性。双硫杂菊酯类似物显示缺乏预期的构象变化，并且显示出良好的分辨能力室温下的1 H NMR共振。另一方面，草叶磷灰素类似物采用呋喃倒置的几何形状，并且环倒置与质子化状态无关。草酸萘并卟啉在613 nm处也显示出弱的荧光发射。
• Core-modified porphyrins. Part 4: Steric effects on photophysical and biological properties in vitro
  作者：Youngjae You、Scott L. Gibson、Russell Hilf、Tymish Y. Ohulchanskyy、Michael R. Detty

  DOI：10.1016/j.bmc.2004.12.048

  日期：2005.3

  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.