2-Hydroxy-6-nitrobenzylbromid | 57356-30-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-Hydroxy-6-nitrobenzylbromid
• 英文别名: 2-Hydroxy-5-nitrobenzylbromid；2-(Bromomethyl)-3-nitrophenol
• CAS: 57356-30-6
• 化学式: C₇H₆BrNO₃
• 分子量: 232.034
• InChiKey: KSNHWEHDMIDNQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Hydroxy-6-nitrobenzylbromid 在 三氟乙酸 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  Photoactivatable BODIPYs Designed To Monitor the Dynamics of Supramolecular Nanocarriers

  摘要：

  Self-assembling nanoparticles of amphiphilic polymers can transport hydrophobic molecules across hydrophilic media and, as a result, can be valuable delivery vehicles for a diversity of biomedical applications. Strategies to monitor their dynamics noninvasively and in real time are, therefore, essential to investigate their translocation within soft matrices and, possibly, rationalize the mechanisms responsible for their diffusion in biological media. In this context, we designed molecular guests with photoactivatable fluorescence for these supramolecular hosts and demonstrated that the activation of the fluorescent cargo, under optical control, permits the tracking of the nanocarrier translocation across hydrogel matrices with the sequential acquisition of fluorescence images. In addition, the mild illumination conditions sufficient to implement these operating principles permit fluorescence activation within developing Drosophila melanogaster embryos and enable the monitoring of the loaded nanocarriers for long periods of time with no cytotoxic effects and no noticeable influence on embryogenesis. These photoresponsive compounds combine a borondipyrromethene (BODIPY) chromophore and a photocleavable oxazine within their covalent skeleton. Under illumination at an appropriate activation wavelength, the oxazine ring cleaves irreversibly to bring the adjacent BODIPY fragment in conjugation with an indole heterocycle. This structural transformation shifts bathochromically the BODIPY absorption and permits the selective excitation of the photochemical product with concomitant fluorescence. In fact, these operating principles allow the photoactivation of BODIPY fluorescence with large brightness and infinite contrast. Thus, our innovative structural design translates into activatable fluorophores with excellent photochemical and photophysical properties as well as provides access to a general mechanism for the real-time tracking of supramolecular nanocarriers in hydrophilic matrices.

  DOI：

  10.1021/ja5125308
• 作为产物：
  描述：

  2-甲基-3-硝基苯甲醚 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 三溴化硼 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 2-Hydroxy-6-nitrobenzylbromid
  参考文献：
  名称：

  Photoactivatable BODIPYs Designed To Monitor the Dynamics of Supramolecular Nanocarriers

  摘要：

  Self-assembling nanoparticles of amphiphilic polymers can transport hydrophobic molecules across hydrophilic media and, as a result, can be valuable delivery vehicles for a diversity of biomedical applications. Strategies to monitor their dynamics noninvasively and in real time are, therefore, essential to investigate their translocation within soft matrices and, possibly, rationalize the mechanisms responsible for their diffusion in biological media. In this context, we designed molecular guests with photoactivatable fluorescence for these supramolecular hosts and demonstrated that the activation of the fluorescent cargo, under optical control, permits the tracking of the nanocarrier translocation across hydrogel matrices with the sequential acquisition of fluorescence images. In addition, the mild illumination conditions sufficient to implement these operating principles permit fluorescence activation within developing Drosophila melanogaster embryos and enable the monitoring of the loaded nanocarriers for long periods of time with no cytotoxic effects and no noticeable influence on embryogenesis. These photoresponsive compounds combine a borondipyrromethene (BODIPY) chromophore and a photocleavable oxazine within their covalent skeleton. Under illumination at an appropriate activation wavelength, the oxazine ring cleaves irreversibly to bring the adjacent BODIPY fragment in conjugation with an indole heterocycle. This structural transformation shifts bathochromically the BODIPY absorption and permits the selective excitation of the photochemical product with concomitant fluorescence. In fact, these operating principles allow the photoactivation of BODIPY fluorescence with large brightness and infinite contrast. Thus, our innovative structural design translates into activatable fluorophores with excellent photochemical and photophysical properties as well as provides access to a general mechanism for the real-time tracking of supramolecular nanocarriers in hydrophilic matrices.

  DOI：

  10.1021/ja5125308

文献信息

• Photochemical Barcodes
  作者：Sicheng Tang、Yang Zhang、Pravat Dhakal、Laura Ravelo、Cheyenne L. Anderson、Kevin M. Collins、Françisco M. Raymo

  DOI：10.1021/jacs.8b00887

  日期：2018.4.4

  wavelengths and mild illumination sufficient to induce these transformations permit the photochemical barcoding of beads also in living nematodes. Different regions of the same animal can be labeled with distinct barcodes to allow the monitoring of their dynamics for long times with no toxic effects. Thus, our photochemical strategy for the generation of fluorescence barcodes can produce multiple and distinguishable

  围绕可光活化的硼二吡咯亚甲基 (BODIPY) 的独特特性设计了一种在体内编码具有空间控制的荧光信号的光化学策略。两个恶嗪在单个 BODIPY 侧翼的光诱导断开，在两个连续步骤中产生三个发射分子的混合物，聚合物珠内具有解析的荧光。通过调整激活光子的剂量以标记具有不同荧光信号代码的单个粒子，可以精确调节每个珠子中三种荧光团的相对数量和发射强度。足以诱导这些转变的可见波长和温和的光照允许在活的线虫中对珠子进行光化学条形码编码。同一动物的不同区域可以用不同的条形码标记，以便长时间监测它们的动态，而不会产生毒性作用。因此，我们用于生成荧光条码的光化学策略可以在同一生物样本中产生多个可区分的标签，以实现对无法区分的目标的时空跟踪。
• A Photoswitchable Fluorophore for the Real‐Time Monitoring of Dynamic Events in Living Organisms
  作者：Yang Zhang、Sicheng Tang、Lorenzo Sansalone、James D. Baker、Françisco M. Raymo

  DOI：10.1002/chem.201603545

  日期：2016.10.10

  This study reports the synthesis of a photoactivatable fluorophore with optimal photochemical and photophysical properties for the real‐time tracking of motion in vivo. The photoactivation mechanism designed into this particular compound permits the conversion of an emissive reactant into an emissive product with resolved fluorescence, under mild illumination conditions that are impossible to replicate

  这项研究报告了具有最佳光化学和光物理特性的可光活化荧光团的合成，可用于实时跟踪体内运动。在特殊的化合物中设计的光活化机理可以使发光反应物在温和的照明条件下转化为具有分解的荧光的发光产物，而这种条件在常规的基于漂白的转换方案中是无法复制的。的确，这些光开关探针的超分子递送到果蝇的果蝇胚盘中胚胎可以实时显示易位分子的变化，而对发育中的生物没有不利影响。因此，这种用于荧光光激活的创新机制可以发展成为监测活生物标本中动态过程的通用化学工具。
• Catalyst-Free [4+2] Cycloaddition of Ynamides with 2-Halomethyl Phenols To Construct 2-Amino-4<i>H</i>-Chromenes and α-Halo Enamides Simultaneously
  作者：Hao Wen、Weibo Yan、Ping Chen、Yu Li、Yu Tang

  DOI：10.1021/acs.joc.0c01258

  日期：2020.10.16

  We report the development of a facile protocol for the [4+2] cycloaddition of ynamides and 2-halomethyl phenols to afford the corresponding 2-amino-4H-chromenes and α-halo enamides under catalyst-free conditions. The reaction proceeds under mild conditions and exhibits good tolerance toward various functional groups and generates high yields. The plausible mechanism involves the formation of an active

  我们报道了在无催化剂条件下为酰胺和2-卤代甲基苯酚的[4 + 2]环加成反应提供相应的2-氨基-4 H-色烯和α-卤代酰胺的简便方案的发展。反应在温和的条件下进行，对各种官能团表现出良好的耐受性，并产生高收率。可能的机理包括活性中间体酮亚胺以及邻亚甲基醌的形成。
• Electron impact studies. Part XCIV. Retro-Diels–Alder reaction in negative-ion mass spectrometry. Nitro-2H,4H-1,3- and -2,3-dihydro-1,4-benzodioxins
  作者：John H. Bowie、Ah Chai Ho

  DOI：10.1039/p29750000724

  日期：——

  The first examples of specific retro-Diels–Alder reactions occurring from negative ions are reported for nitro-2H,4H-1,3- and -2,3-dihydro-1,4-benzodioxins. The extent of the retro-reaction from the nitro-1,3-benzodioxins is dependent upon the position of the nitro-group relative to the oxygenated ring. The fragmentation of model compounds has been used in order to rationalise the mechanism(s) of the

  对于硝基2 H，4 H -1,3-和-2,3-二氢-1,4-苯并二恶英，报道了由负离子引起的特定的逆Diels-Alder反应的第一个例子。硝基-1,3-苯并二恶英的逆反应程度取决于硝基相对于氧化环的位置。为了使各种重排过程的机理合理化，已经使用了模型化合物的碎片化方法。
• Fluorescence patterning with mild illumination in polymer films of photocleavable oxazines
  作者：Ek Raj Thapaliya、Yang Zhang、Françisco M. Raymo

  DOI：10.1039/c6tc05532j

  日期：——

  The photoinduced cleavage of oxazine heterocycles, connected to macromolecules spin coated on appropriate substrates, occurs efficiently and irreversibly to quench the emission of a fluorescent dopant and allow the imprinting of patterns.

  在适当的基底上旋涂的与大分子连接的噁唑杂环的光诱导断裂，能够高效且不可逆地熄灭荧光掺杂剂的发射，并允许印刷图案。