2-hydroxy-6-(2-hydroxy)ethoxynaphthalene | 10441-37-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-6-(2-hydroxy)ethoxynaphthalene
• 英文别名: 6-(2-hydroxyethoxy)naphthalene-2-ol；6-(2-hydroxyethoxy)naphthalen-2-ol
• CAS: 10441-37-9
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: BXHPQSOXUBUGQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  422.7±20.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-6-(2-hydroxy)ethoxynaphthalene 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 18.0h， 生成 8-(2-(pent-4-enoyloxy)ethoxy)-3-(4-(pent-4-enoyloxy)phenyl)-3-phenyl-3H-naphtho[2,1-b]pyran
  参考文献：
  名称：

  Regioisomer-Specific Mechanochromism of Naphthopyran in Polymeric Materials

  摘要：

  Transformation of naphthopyran into a colored merocyanine species in polymeric materials is achieved using mechanical force. We demonstrate that the mechanochemical reactivity of naphthopyran is critically dependent on the regiochemistry, with only one particular substitution pattern leading to successful mechanochemical activation. Two alternative regioisomers with different polymer attachment points are demonstrated to be mechanochemically inactive. This trend in reactivity is accurately predicted by DFT calculations, reinforcing predictive capabilities in mechanochemical systems. We rationalize the reactivity differences between naphthopyran regioisomers in terms of the alignment of the target C-O pyran bond with the direction of the applied mechanical force and its effect on mechanochemical transduction along the reaction coordinate.

  DOI：

  10.1021/jacs.6b07610
• 作为产物：
  描述：

  碳酸乙烯酯 、 2,6-萘二酚 在 sodium iodide 作用下， 反应 1.0h， 以24%的产率得到2-hydroxy-6-(2-hydroxy)ethoxynaphthalene
  参考文献：
  名称：

  Regioisomer-Specific Mechanochromism of Naphthopyran in Polymeric Materials

  摘要：

  Transformation of naphthopyran into a colored merocyanine species in polymeric materials is achieved using mechanical force. We demonstrate that the mechanochemical reactivity of naphthopyran is critically dependent on the regiochemistry, with only one particular substitution pattern leading to successful mechanochemical activation. Two alternative regioisomers with different polymer attachment points are demonstrated to be mechanochemically inactive. This trend in reactivity is accurately predicted by DFT calculations, reinforcing predictive capabilities in mechanochemical systems. We rationalize the reactivity differences between naphthopyran regioisomers in terms of the alignment of the target C-O pyran bond with the direction of the applied mechanical force and its effect on mechanochemical transduction along the reaction coordinate.

  DOI：

  10.1021/jacs.6b07610

文献信息

• Toward modulation of the naphthopyran photochromism: a miniemulsion copolymerization strategy
  作者：Dehua Li、Meiduo Zhang、Guang Wang、Shuangxi Xing

  DOI：10.1039/c3nj01313h

  日期：——

  Novel naphthopyran derivative based photochromic polymer nanoparticles are prepared via miniemulsion copolymerization with methyl methacrylate (MMA) and n-butyl methacrylate (BMA) monomers. The systematic modulation of the photochromic rate can be achieved via tuning the ratio of MMA and BMA monomers to lead the naphthopyrans to swing between rigid and soft surroundings. Transmission electron micrographs

  通过与甲基丙烯酸甲酯（MMA）和甲基丙烯酸正丁酯（BMA）单体进行细乳液共聚制备了新型的基于萘并吡喃衍生物的光致变色聚合物纳米粒子。光致变色速率的系统的调制可以实现经由调整MMA和BMA单体的比例，以使萘并吡喃在刚性和柔软的环境之间摇摆。透射电子显微照片（TEM）和动态光散射（DLS）图像证明纳米颗粒是离散且光滑的。聚合物纳米颗粒中萘并吡喃的典型光谱特征表明，光致色素成功地掺入了纳米颗粒中。另外，该聚合物纳米颗粒在UV辐射和热逆反应时显示出良好的光致变色可逆性和稳定性。
• Preparation and photochromic properties of layer-by-layer self-assembly films and light-responsive micelles based on amphiphilic naphthopyran derivative
  作者：Meiduo Zhang、Dehua Li、Yi He、Guang Wang

  DOI：10.1016/j.saa.2015.06.082

  日期：2015.12

  An amphiphilic naphthopyran derivative (DSNP) with negative-charged di-sulfatoethoxy was first designed and synthesized. DSNP was used to prepare the LBL self-assembly films with cationic quaternized poly(4-vinylpyridine) (P4VPQ). The multilayer assembly process was monitored via UV-Vis spectra and the DSNP displayed a significant slow fading rate in film. In addition, DSNP was also used as the light-responsive

  首先设计并合成了带负电荷的二硫酸基乙氧基的两亲萘并吡喃衍生物（DSNP）。DSNP用于制备带有阳离子季铵化聚（4-乙烯基吡啶）（P4VPQ）的LBL自组装膜。通过UV-Vis光谱监测多层组装过程，并且DSNP在膜中显示出显着的缓慢的褪色速率。另外，DSNP还用作光响应基团，以与聚乙二醇-三乙胺溴化物（PEG-NEt3）一起制造光响应胶束。萘并吡喃部分的光异构化可以快速和可逆地调节胶束的分解和重新组装。聚合物胶束水溶液中尼罗红（NR）荧光光谱的变化表明，该聚合物胶束可作为纳米载体进行包封，根据需要控制光辐照释放并重新封装客体溶质。结果表明，两亲性萘并吡喃可用于光开关和生物医学领域中的药物递送。