7-(2-hydroxyethoxy)naphthalene-2-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-(2-hydroxyethoxy)naphthalene-2-ol
• 英文别名: 7-(2-Hydroxyethoxy)naphthalen-2-ol
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: WIURKMDSVSVDOQ-UHFFFAOYSA-N

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：

  7-(2-hydroxyethoxy)naphthalene-2-ol 在 4-二甲氨基吡啶 、 铂(0)-1,3-二乙烯-1,1,3,3-四甲基二硅氧烷 、 三乙胺 作用下， 以 四氢呋喃 、 5,5-dimethyl-1,3-cyclohexadiene 、 甲苯 为溶剂， 反应 22.0h， 生成
  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 、 2,7-二羟基萘 在 四丁基碘化铵 作用下， 反应 1.0h， 以39%的产率得到7-(2-hydroxyethoxy)naphthalene-2-ol
  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

• Regioisomer-Specific Mechanochromism of Naphthopyran in Polymeric Materials
  作者：Maxwell J. Robb、Tae Ann Kim、Abigail J. Halmes、Scott R. White、Nancy R. Sottos、Jeffrey S. Moore

  DOI：10.1021/jacs.6b07610

  日期：2016.9.28

  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.