2-chloro-3-[2-(2-{3-[2-(2-hydroxyethoxy)ethoxy]naphthalen-2-yloxy}ethoxy)ethoxy]-1,4-naphthoquinone | 444348-85-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-chloro-3-[2-(2-{3-[2-(2-hydroxyethoxy)ethoxy]naphthalen-2-yloxy}ethoxy)ethoxy]-1,4-naphthoquinone
• 英文别名: 2-Chloro-3-[2-[2-[3-[2-(2-hydroxyethoxy)ethoxy]naphthalen-2-yl]oxyethoxy]ethoxy]naphthalene-1,4-dione
• CAS: 444348-85-0
• 化学式: C₂₈H₂₇ClO₈
• 分子量: 526.971
• InChiKey: CFMZPXBDOBHDRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-chloro-3-[2-(2-{3-[2-(2-hydroxyethoxy)ethoxy]naphthalen-2-yloxy}ethoxy)ethoxy]-1,4-naphthoquinone 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 66.0h， 以63%的产率得到2,5,8,19,22,25-hexaoxapentacyclo[24.8.0.09,18.011,16.028,33]tetratriaconta-1(34),9(18),11,13,15,26,28,30,32-nonaene-10,17-dione
  参考文献：
  名称：

  摘要：

  The bichromophoric crown ether N18C6NQ (1) has been synthesized in three steps from readily available starting materials. The main theme of the synthetic strategy involves the conjugate addition of an alcohol to 2,3-dichloronaphthoquinone in the presence of a base. Preliminary electrochemical and photophysical studies on (1) have been undertaken. The addition of alkali metal cations to the crown ether (1) causes significant changes in the first and second reduction potentials of the naphthoquinone (NQ) chromophore. In the case of the first process, a correlation between the reversible potential and cation 'fit' exists. The steady-state fluorescence spectra of (1) are quenched substantially (> 90%) as compared with the model (2) in both CH 2 Cl 2 and dimethylformamide solution. These systems are of interest in the development of a new family of crown ether based photosynthetic mimics and ion-selective sensors.

  DOI：

  10.1071/ch02030
• 作为产物：
  描述：

  2,3-二羟基萘 在 potassium carbonate 、 三乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 96.0h， 生成 2-chloro-3-[2-(2-{3-[2-(2-hydroxyethoxy)ethoxy]naphthalen-2-yloxy}ethoxy)ethoxy]-1,4-naphthoquinone
  参考文献：
  名称：

  摘要：

  The bichromophoric crown ether N18C6NQ (1) has been synthesized in three steps from readily available starting materials. The main theme of the synthetic strategy involves the conjugate addition of an alcohol to 2,3-dichloronaphthoquinone in the presence of a base. Preliminary electrochemical and photophysical studies on (1) have been undertaken. The addition of alkali metal cations to the crown ether (1) causes significant changes in the first and second reduction potentials of the naphthoquinone (NQ) chromophore. In the case of the first process, a correlation between the reversible potential and cation 'fit' exists. The steady-state fluorescence spectra of (1) are quenched substantially (> 90%) as compared with the model (2) in both CH 2 Cl 2 and dimethylformamide solution. These systems are of interest in the development of a new family of crown ether based photosynthetic mimics and ion-selective sensors.

  DOI：

  10.1071/ch02030