2-[1-phenyl-1-(tert-butyldimethylsilyloxy)methyl]thiophene | 596104-73-3

• 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-[1-phenyl-1-(tert-butyldimethylsilyloxy)methyl]thiophene
• 英文别名: 2-[(tert-butyldimethylsilyloxy)(phenyl)methyl]thiophene；2-[(tert-butyldimethylsiloxy)phenylmethyl]thiophene；Silane, (1,1-dimethylethyl)dimethyl(phenyl-2-thienylmethoxy)-；tert-butyl-dimethyl-[phenyl(thiophen-2-yl)methoxy]silane
• CAS: 596104-73-3
• 化学式: C₁₇H₂₄OSSi
• 分子量: 304.528
• InChiKey: NDFFPHUVHSJLBZ-UHFFFAOYSA-N

物化性质

• 沸点：
  367.5±27.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.86
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[1-phenyl-1-(tert-butyldimethylsilyloxy)methyl]thiophene 在 正丁基锂 、 四甲基乙二胺 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 2-[hydroxy(phenyl)methyl]-5-[hydroxy(4-trifluoromethylphenyl)methyl]thiophene
  参考文献：
  名称：

  核心修饰的卟啉。第5部分：电子对体外光物理和生物学特性的影响。

  摘要：

  制备了21,23-二硫卟啉2-11作为5,20-二苯基-10,15-双（4-羧基甲氧基甲氧基）苯基-21,23-二硫卟啉1的类似物，以检查电子特性对5-和20的影响-中位。就吸收光谱，产生单线态氧和荧光的量子产率而言，在介孔环上电子性质的影响并不显着。尽管在正辛醇/ pH 7.4缓冲液分配系数中注意到了一些差异，但在化合物之间，log D（7.4）的对数D（7.4）并未严重影响细胞的摄取或光毒性。浓度高达1 x 10（-5）M的双硫卟啉1-11均未显示出暗毒性。用5 J cm（-2）的350-750 nm光照射后，五种卟啉2、3、5、6 在5 x 10（-7）M光敏剂下，有8例杀死了80％以上的R3230AC大鼠乳腺癌细胞。在这五种化合物中，带有5-苯基和20-（4-氟苯基）取代基的化合物3是对R3230AC细胞最有效的光敏剂，在1 x 10（-7）M 3处显示67％的细胞杀伤力。 20位使光敏剂具有最小的光毒性。

  DOI：

  10.1016/j.bmc.2005.07.006
• 作为产物：
  描述：

  苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 4-二甲氨基吡啶 、 正丁基锂 、 三乙胺 作用下， 以 正己烷 为溶剂， 生成 2-[1-phenyl-1-(tert-butyldimethylsilyloxy)methyl]thiophene
  参考文献：
  名称：

  核心修饰的卟啉。第5部分：电子对体外光物理和生物学特性的影响。

  摘要：

  制备了21,23-二硫卟啉2-11作为5,20-二苯基-10,15-双（4-羧基甲氧基甲氧基）苯基-21,23-二硫卟啉1的类似物，以检查电子特性对5-和20的影响-中位。就吸收光谱，产生单线态氧和荧光的量子产率而言，在介孔环上电子性质的影响并不显着。尽管在正辛醇/ pH 7.4缓冲液分配系数中注意到了一些差异，但在化合物之间，log D（7.4）的对数D（7.4）并未严重影响细胞的摄取或光毒性。浓度高达1 x 10（-5）M的双硫卟啉1-11均未显示出暗毒性。用5 J cm（-2）的350-750 nm光照射后，五种卟啉2、3、5、6 在5 x 10（-7）M光敏剂下，有8例杀死了80％以上的R3230AC大鼠乳腺癌细胞。在这五种化合物中，带有5-苯基和20-（4-氟苯基）取代基的化合物3是对R3230AC细胞最有效的光敏剂，在1 x 10（-7）M 3处显示67％的细胞杀伤力。 20位使光敏剂具有最小的光毒性。

  DOI：

  10.1016/j.bmc.2005.07.006

文献信息

• 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.
• Water Soluble, Core-Modified Porphyrins. 3. Synthesis, Photophysical Properties, and in Vitro Studies of Photosensitization, Uptake, and Localization with Carboxylic Acid-Substituted Derivatives
  作者：Youngjae You、Scott L. Gibson、Russell Hilf、Sherry R. Davies、Allan R. Oseroff、Indrajit Roy、Tymish Y. Ohulchanskyy、Earl J. Bergey、Michael R. Detty

  DOI：10.1021/jm030136i

  日期：2003.8.1

  Water soluble, core-modified porphyrins 1-5 bearing 1-4 carboxylic acid groups were prepared and evaluated in vitro as photosensitizers for photodynamic therapy. The 21,23-core-modified porphyrins 1-5 gave band I absorption maxima with lambda(max) of 695-701 nm. The number of carboxylic acid groups in the dithiaporphyrins 1-4 had little effect on either absorption maxima (lambda(max) of 696-701 nm for band 1) or quantum yields of singlet oxygen generation [phi(O-1(2)) of 0.74-0.80]. Substituting two Se atoms for S gave a shorter band I absorption maximum (lambda(max) of 695 nm) and a smaller value for the quantum yield for generation of singlet oxygen [phi(O-1(2)) of 0.30]. The phototoxicity of 1-5 was evaluated against R3230AC cells. The phototoxicities of dithiaporphyrin 2, sulfonated thiaporphyrin 30, HPPH, and Photofrin were also evaluated against Colo-26 cells in culture using 4 J cm(-2) of 570-800 nm light. Compound 2 was significantly more phototoxic than sulfonated dithiaporphyrin 30, HPPH, or Photofrin. Cellular uptake was much greater for compounds 1, 2, and 5 relative to compounds 3 and 4. Confocal scanning laser microscopy and double labeling experiments with rhodamine 123 suggested that the mitochondria were an important target for dithiaporphyrins 1 and 2. Inhibition of mitochondrial cytochrome c oxidase activity in whole R3230AC cells was observed in the dark with compounds 1 and 30 and both in the dark and in the light with core-modified porphyrin 2.
• Core-modified porphyrins. Part 5: Electronic effects on photophysical and biological properties in vitro
  作者：Youngjae You、Scott L. Gibson、Michael R. Detty

  DOI：10.1016/j.bmc.2005.07.006

  日期：2005.11

  to 1 x 10(-5) M. Once irradiated with 5 J cm(-2) of 350-750 nm light, five porphyrins 2, 3, 5, 6, and 8 killed over 80% of R3230AC rat mammary adenocarcinoma cells at 5 x 10(-7) M photosensitizer. Among these five, compound 3 bearing 5-phenyl and 20-(4-fluorophenyl) substituents was the most potent photosensitizer toward R3230AC cells showing 67% cell kill at 1 x 10(-7) M 3. Bulky substituents at the

  制备了21,23-二硫卟啉2-11作为5,20-二苯基-10,15-双（4-羧基甲氧基甲氧基）苯基-21,23-二硫卟啉1的类似物，以检查电子特性对5-和20的影响-中位。就吸收光谱，产生单线态氧和荧光的量子产率而言，在介孔环上电子性质的影响并不显着。尽管在正辛醇/ pH 7.4缓冲液分配系数中注意到了一些差异，但在化合物之间，log D（7.4）的对数D（7.4）并未严重影响细胞的摄取或光毒性。浓度高达1 x 10（-5）M的双硫卟啉1-11均未显示出暗毒性。用5 J cm（-2）的350-750 nm光照射后，五种卟啉2、3、5、6 在5 x 10（-7）M光敏剂下，有8例杀死了80％以上的R3230AC大鼠乳腺癌细胞。在这五种化合物中，带有5-苯基和20-（4-氟苯基）取代基的化合物3是对R3230AC细胞最有效的光敏剂，在1 x 10（-7）M 3处显示67％的细胞杀伤力。 20位使光敏剂具有最小的光毒性。