1-(trimethylsilyl)naphthalen-2-ol | 18081-07-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(trimethylsilyl)naphthalen-2-ol
• 英文别名: 1-trimethylsilanyl-[2]naphthol；1-Trimethylsilyl-[2]naphthol；1-Trimethylsilylnaphthalen-2-ol；1-trimethylsilylnaphthalen-2-ol
• CAS: 18081-07-7
• 化学式: C₁₃H₁₆OSi
• 分子量: 216.355
• InChiKey: VRCNDVIHFFHHOV-UHFFFAOYSA-N

物化性质

• 沸点：
  126-127 °C(Press: 0.5 Torr)
• 密度：
  1.002 g/cm3(Temp: 24 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(trimethylsilyl)naphthalen-2-ol 在 potassium fluoride 、 正丁基锂 、 全氟碘代丁烷 、 cis-dicyclohexano-18-C-6 、 碳酸二甲酯 作用下， 以 四氢呋喃 为溶剂， 反应 14.5h， 生成 1-iodo-2-(trifluoromethoxy)naphthalene
  参考文献：
  名称：

  三氟甲基芳基磺酸盐（TFMS）：适用的三氟甲氧基化试剂

  摘要：

  氮之后，氟可能是掺入小分子中的另一个最受欢迎的杂原子。在许多含氟基团中，三氟甲基芳基醚（ArOCF 3）在药物设计中具有独特的特性，难以合成，因此开发了许多不同的方法来制备它们。的一种新的一锅法合成ø -碘-芳基三氟甲基醚（ArOCF 3 I）用的反应描述trifluoromethoxylation和碘化与三氟甲基芳基磺酸盐（TFMS）在该手稿。通过筛选不同的溶剂，冠醚，底物来优化反应条件，并且产物的比例和收率处于中等至高收率（高达86％）。

  DOI：

  10.1016/j.tetlet.2019.04.033
• 作为产物：
  描述：

  1-溴-2-萘酚 在 正丁基锂 作用下， 生成 1-(trimethylsilyl)naphthalen-2-ol
  参考文献：
  名称：

  Some Substituted Naphthylsilanes

  摘要：

  DOI：

  10.1021/ja01167a009

文献信息

• Novel One-Pot Synthesis of Xanthones via Sequential Fluoride Ion-Promoted Fries-Type Rearrangement and Nucleophilic Aromatic Substitution
  作者：Takashi Matsumoto、Yuuki Fujimoto、Ryohei Itakura、Hiroki Hoshi、Hikaru Yanai、Yoshio Ando、Keisuke Suzuki

  DOI：10.1055/s-0033-1339881

  日期：——

  A novel and efficient synthesis of xanthones is described. 2-(Trimethylsilyl)phenyl 2-fluorobenzoate derivatives undergo Fries-type rearrangement and intramolecular SNAr reaction in a one-pot sequential manner under fluoride ion-promoted mild conditions. The method provides efficient access to xanthones that have significant steric congestion around the C9 carbonyl, which are not readily available

  描述了一种新型有效的氧杂蒽酮合成方法。2-（三甲基甲硅烷基）苯基 2-氟苯甲酸酯衍生物在氟离子促进的温和条件下以一锅顺序方式进行 Fries 型重排和分子内 SNAr 反应。该方法提供了对在 C9 羰基周围具有显着空间拥塞的氧杂蒽酮的有效获取，这些氧杂蒽酮不容易通过常规方法获得。
• Continuous-Flow Synthesis of Trimethylsilylphenyl Perfluorosulfonate Benzyne Precursors
  作者：Boris Michel、Michael F. Greaney

  DOI：10.1021/ol500959e

  日期：2014.5.16

  2-(Trimethylsilyl)phenyl perfluorosulfonated aryne precursors may now be accessed using flow chemistry, enabling the fast preparation of pure compounds with no requirement for low temperature lithiation or column chromatography. The process has been adapted to novel nonaflate precursors, utilizing the cheaper and more user-friendly nonaflyl fluoride reagent. The resultant nonaflates are shown to successfully

  现在可以使用流式化学方法检测2-（三甲基甲硅烷基）苯基全氟磺化的芳烃前体，从而可以快速制备纯净的化合物，而无需低温锂化或柱色谱法。该方法已利用便宜和更用户友好的壬二酰氟试剂应用于新型壬二酸酯前体。所得的壬二酸酯显示出成功地参与了一系列的芳烃反应类别。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 28, page 86 - 90
  作者：

  DOI：——

  日期：——
• N,N‐Diarysulfonamide reduces proinflammatory cytokine interleukin‐6 levels in cells through nuclear factor‐κB regulation
  作者：Dattatraya Babar、Gopinath Khansole、Vishalkumar Singh、Akash Shinde、Vaishnavi Kambhampati、Sai Balaji Andugulapati、Haridas B. Rode

  DOI：10.1002/cmdc.202300598

  日期：——

  The synthesized sulfonamides were evaluated for cytotoxicity followed by the cytokine/inflammatory marker’s inhibition capability and its mechanism of action in RAW‐264.7 cells. Elevated interleukin‐6 (IL‐6) levels have been reported in inflammatory conditions and inflammation‐associated disorders. Hence, reducing the IL‐6 levels in inflammatory conditions can serve as an attractive therapeutic target in dealing the inflammation. Among 42 compounds, seven compounds showed significant inhibition of IL‐6 levels in lipopolysaccharide (LPS) challenged RAW‐264.7 cells at 12.5 µM concentration. Further, investigation revealed that the IC50 value of these compounds for reducing IL‐6 levels was found to be in the range of 9.7 to 2.6 µM. The promising compounds 5y (IC50 of 2.6 µM) and 5n (IC50 of 4.1 µM) along with other derivatives fulfil drug‐likeness parameters laid down by Lipinski’s rule of five. Further, analysis using RTqPCR and Western‐blot analysis revealed that treatment with 5n significantly reduced the expression of pro‐inflammatory, inflammatory and macrophage marker’s expression (IL‐1β, CCL2, COX2 and CD68) compared to LPS control. The mechanistic evaluation showed that RL‐442 exhibited anti‐inflammatory properties by modulating the nuclear factor‐κB (NF‐κB) activation. The identified compound can be a promising candidate for further discovery efforts to generate a preclinical candidate effective in inflammation.
• Some Substituted Naphthylsilanes
  作者：S. V. Sunthankar、Henry Gilman

  DOI：10.1021/ja01167a009

  日期：1950.11