N-<(2-Hydroxy-3-naphthyl)carbonyl>-monoaza-12-crown-4 | 154416-69-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-<(2-Hydroxy-3-naphthyl)carbonyl>-monoaza-12-crown-4
• CAS: 154416-69-0
• 化学式: C₁₉H₂₃NO₅
• 分子量: 345.395
• InChiKey: YTYJYJJNALNKTD-UHFFFAOYSA-N

物化性质

• 沸点：
  575.4±50.0 °C(predicted)
• 密度：
  1.204±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  68.23
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-<(2-Hydroxy-3-naphthyl)carbonyl>-monoaza-12-crown-4 在 lithium aluminium tetrahydride 、 溶剂黄146 、 三乙胺 、 sodium nitrite 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 1,3,3-Trimethyl-5'-<(1,4,7-trioxa-10-azacyclododec-10-yl)methyl>spiro-1,4-oxazine>
  参考文献：
  名称：

  Cation Complexation, Photochromism, and Reversible Ion-Conducting Control of Crowned Spironaphthoxazine

  摘要：

  A spironaphthoxazine derivative incorporating a monaza-12-crown-4 moiety at the 5'-position has been designed as a light-resistant, cation-complexable photochromic compound. Complexation of alkali metal ions by the crown moiety in the crowned spironaphthoxazine allows the spironaphthoxazine skeleton to isomerize to its corresponding open colored form, even under dark conditions. Specifically, Li+ complexation greatly stabilizes the open colored form due to the intramolecular interaction between its oxo group and crown-complexed cation, as well as the selective Li+ complexation of its 12-crown-4 moiety. Taking advantage of the high Li+ selectivity in the cation-induced isomerization of crowned spironaphthoxazine, the thermal stability of the open colored form can be modulated continuously by added Li+ concentrations. Even in the presence of the metal ion, UV- and visible-light irradiation led to further isomerization to the open form and back-isomerization to the initial closed form, respectively. Photoisomerization of crowned spironaphthoxazine to its open form promoted Li+ binding due to the additional axial interaction with the crown-complexed Li+, while that back to the closed form attenuated the cation binding. The photoinduced change in the cation-binding ability of crowned spironaphthoxazine, which possesses high light-fatigue resistance, has led to a highly reversible, photochemical switching system of ionic conduction.

  DOI：

  10.1021/jo00085a009
• 作为产物：
  描述：

  2-羟基-3-萘甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 15.0h， 生成 N-<(2-Hydroxy-3-naphthyl)carbonyl>-monoaza-12-crown-4
  参考文献：
  名称：

  Cation Complexation, Photochromism, and Reversible Ion-Conducting Control of Crowned Spironaphthoxazine

  摘要：

  A spironaphthoxazine derivative incorporating a monaza-12-crown-4 moiety at the 5'-position has been designed as a light-resistant, cation-complexable photochromic compound. Complexation of alkali metal ions by the crown moiety in the crowned spironaphthoxazine allows the spironaphthoxazine skeleton to isomerize to its corresponding open colored form, even under dark conditions. Specifically, Li+ complexation greatly stabilizes the open colored form due to the intramolecular interaction between its oxo group and crown-complexed cation, as well as the selective Li+ complexation of its 12-crown-4 moiety. Taking advantage of the high Li+ selectivity in the cation-induced isomerization of crowned spironaphthoxazine, the thermal stability of the open colored form can be modulated continuously by added Li+ concentrations. Even in the presence of the metal ion, UV- and visible-light irradiation led to further isomerization to the open form and back-isomerization to the initial closed form, respectively. Photoisomerization of crowned spironaphthoxazine to its open form promoted Li+ binding due to the additional axial interaction with the crown-complexed Li+, while that back to the closed form attenuated the cation binding. The photoinduced change in the cation-binding ability of crowned spironaphthoxazine, which possesses high light-fatigue resistance, has led to a highly reversible, photochemical switching system of ionic conduction.

  DOI：

  10.1021/jo00085a009