10-(tert-butyldimethylsilyl)-phenoxazine | 113202-18-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 10-(tert-butyldimethylsilyl)-phenoxazine
• 英文别名: N-t-butyldimethylsilylphenoxazine；tert-butyl-dimethyl-phenoxazin-10-ylsilane
• CAS: 113202-18-9
• 化学式: C₁₈H₂₃NOSi
• 分子量: 297.472
• InChiKey: CANOYJKASGFWPH-UHFFFAOYSA-N

物化性质

• 熔点：
  57 °C
• 沸点：
  352.0±25.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.94
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  10-(tert-butyldimethylsilyl)-phenoxazine 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.25h， 生成 4-formylphenoxazine
  参考文献：
  名称：

  Regiospecific lithiation of phenoxazine ortho to the oxygen atom. Synthesis of 4-mono- and 4,6-disubstituted phenoxazine derivatives

  摘要：

  DOI：

  10.1021/jo00270a027
• 作为产物：
  描述：

  吩噁嗪 在 正丁基锂 、 sodium hydride 作用下， 反应 5.33h， 生成 10-(tert-butyldimethylsilyl)-phenoxazine
  参考文献：
  名称：

  Regiospecific lithiation of phenoxazine ortho to the oxygen atom. Synthesis of 4-mono- and 4,6-disubstituted phenoxazine derivatives

  摘要：

  DOI：

  10.1021/jo00270a027

文献信息

• A naked-eye colorimetric sensor for chloroform
  作者：Kai Sheng、Haifeng Lu、Anbang Sun、Yanmin Wang、Yuantao Liu、Feng Chen、Wenchao Bian、Yang Li、Rui Kuang、Di Sun

  DOI：10.1016/j.cclet.2019.01.027

  日期：2019.4

  molecule shows selective fast response towards halogenated solvent via naked-eye detectable chromism. SP shows colorless solution when dissolved in most solvents initially but changes to blue color in chloroform under UV irradiation (λ = 365 nm) within 5 s. The luminescence spectra of SP in halogenated solvent show a large bathochromic shift (> 100 nm) with 60-fold enhanced emission intensity compared to

  摘要已合成了一种称为SP的基于苯恶嗪的分子，并将其用作卤代溶剂的选择性传感器。该分子通过肉眼可检测的色度显示出对卤代溶剂的选择性快速响应。当最初溶解在大多数溶剂中时，SP呈无色溶液，但在5秒钟内在UV辐射（λ= 365 nm）下在氯仿中变为蓝色。与不含卤素的溶剂相比，SP在卤代溶剂中的发光光谱显示出较大的红移（> 100 nm），发射强度提高了60倍。还值得一提的是，SP分子与卤代溶剂之间发生了光诱导反应。在详细的核磁共振，荧光和质谱的基础上，提出了可能的自由基反应机理。
• 4-monosubstituted and 4,6-disubstituted phenoxazines
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04707473A1

  公开（公告）日：1987-11-17

  4-Monosubstitued and 4,6-disubstituted phenoxazines, methods of preparing them and pharmaceutical compositions containing them. These compounds are useful as anti-inflammatories.

  4-单取代和4,6-双取代苯氧噻嗪，其制备方法和含有它们的制药组合物。这些化合物可用作抗炎药。
• 4-monosubstituted and 4,6-disubstituted
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04803269A1

  公开（公告）日：1989-02-07

  4-Monosubstituted and 4,6-disubstituted phenoxazines, methods of preparing them and pharmaceutical compositions containing them. These compounds are useful as anti-inflammatories.

  4-单取代和4,6-双取代苯氧噻嗪，其制备方法和含有它们的制药组合物。这些化合物可用作抗炎药。
• Structure-Based Design of <i>N</i>-Phenyl Phenoxazine Transthyretin Amyloid Fibril Inhibitors
  作者：H. Michael Petrassi、Thomas Klabunde、James Sacchettini、Jeffery W. Kelly

  DOI：10.1021/ja993309v

  日期：2000.3.1

  Starting with the published 2.0 Angstrom X-ray crystal structure of the transthyretin (flufenamic acid)(2) complex, a simple structure-based ligand design strategy was employed to conceive of N-phenyl phenoxazine transthyretin (TTR) amyloid fibril inhibitors. Fifteen N-phenyl phenoxazines were chemically synthesized and evaluated using a quantitative amyloid fibril assay in vitro. The structure of one of the two most active phenoxazines, 4, bound to TTR was solved to a resolution of 1.9 Angstrom to understand the structural basis of its efficacy. N-phenyl phenoxazine 4 binds similar to the orientation anticipated, although not as deeply into the channel as expected. Like flufenamic acid. 4 mediates binding-induced conformational changes that enable intersubunit H-bonding in tetrameric TTR which may be important Tor preventing fibril formation. Analytical ultracentrifugation analysis demonstrates that 4 blocks the first step of TTR amyloid fibril formation, that is, tetramer dissociation to the alternatively folded amyloidogenic monomer. Isothermal titration calorimetry was used to determine the binding constants of 4 to TTR and to dissect the enthalpy and entropy contributions associated with ligand binding. Phenoxazine 4 exhibits binding and inhibitor efficacy against WT TTR that is very similar to that of flufenamic acid, unlike the situation with the inhibition of L55P fibril formation where 4 is superior to Flu as an inhibitor but not as a binder. It is clear that 4 functions in part by stabilizing the normally folded tetramer through formation of the TTR (4)2 complex, which in turn increases the activation energy for tetramer dissociation. The data also suggest that 4 destabilizes the transition state associated with TTR dissociation to the monomeric amyloidogenic intermediate. Future biophysical studies, including kinetic measurements, are needed to understand the exact mechanism(s) of the action of 4.
• MUCHOWSKI, JOSEPH M.;GREENHOUSE, ROBERT J.;GUZMAN, ANGEL
  作者：MUCHOWSKI, JOSEPH M.、GREENHOUSE, ROBERT J.、GUZMAN, ANGEL

  DOI：——

  日期：——