4-((4-(carboxymethoxy)phenyl)azo)benzo-15-crown-5 | 77111-48-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-((4-(carboxymethoxy)phenyl)azo)benzo-15-crown-5
• CAS: 77111-48-9
• 化学式: C₂₂H₂₆N₂O₈
• 分子量: 446.457
• InChiKey: GWOUDJJZDFLGLC-WCWDXBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  117.4
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  4-((4-(carboxymethoxy)phenyl)azo)benzo-15-crown-5 生成
  参考文献：
  名称：

  冠醚与光响应性羧酸盐帽的离子萃取。

  摘要：

  合成了一种新的具有偶氮苯-4-氧乙酸酯功能的光敏冠醚（I）。光异构化的顺式（1）比反式（I）更有选择性地提取K +离子，并且通过添加金属离子抑制了顺式-反式热异构化。

  DOI：

  10.1016/s0040-4039(00)92201-9
• 作为产物：
  描述：

  4'-氨基苯并-15-冠-5-醚 生成 4-((4-(carboxymethoxy)phenyl)azo)benzo-15-crown-5
  参考文献：
  名称：

  冠醚与光响应性羧酸盐帽的离子萃取。

  摘要：

  合成了一种新的具有偶氮苯-4-氧乙酸酯功能的光敏冠醚（I）。光异构化的顺式（1）比反式（I）更有选择性地提取K +离子，并且通过添加金属离子抑制了顺式-反式热异构化。

  DOI：

  10.1016/s0040-4039(00)92201-9

文献信息

• Thermal and Light Control of the Sol-Gel Phase Transition in Cholesterol-Based Organic Gels. Novel Helical Aggregation Modes As Detected by Circular Dichroism and Electron Microscopic Observation
  作者：Kazutaka Murata、Masayoshi Aoki、Tsuyoshi Suzuki、Takaaki Harada、Hirosuke Kawabata、Takashi Komori、Fumio Ohseto、Keiko Ueda、Seiji Shinkai

  DOI：10.1021/ja00094a023

  日期：1994.7

  Nineteen cholesterol derivatives containing a variety of azobenzene moieties coupled to C-3 of a steroidal moiety through an ester linkage were synthesized. We employed two different esterification methods by which cholesterol derivatives with the natural (S)-configuration at C-3 and those with the inverted (R)-configuration at C-3 were obtained (the latter derivatives are indicated by a prime). Among them, cholesterol derivatives bearing a p-alkoxyazobenzene moiety (2R and 2R') acted as excellent thermally-reversible gelators of various organic fluids, but the gelation ability is fairly different between 2R and 2R': 2R could gelatinize hydrocarbons such as n-hexane, n-octane, and toluene, halogen solvents such as 1,2-dichloroethane and dichloromethane, ether solvents such as diethyl ether and THF, and alcohols such as ethanol and I-butanol whereas 2R' could gelatinize ketones, methanol, and polysiloxanes. In general, the solubility of 2R' in apolar solvents is superior to that of 2R, so 2R is useful for gelation of apolar solvents whereas 2R' is useful for gelation of polar solvents. We found that the sol-gel phase transition is sensitively ''read-out'' by a change in the circular dichroism (CD) spectrum: the gel phase is CD-active whereas the sol phase is totally CD-silent. For example, the 2Me-1-butanol gel gave a positive exciton coupling band with (R)-chirality whereas the 2Et'-methanol gel gave a negative exciton coupling band with (S)-chirality. These results mean that dipoles in the azobenzene moiety are oriented in a clockwise (in (R)-chirality) or anticlockwise (in (S)-chirality) direction when they interact in the excited state. Strangely, we accidentally found that the CD sign of the gels prepared from 2Pr, 2Bu, and 3Me' (azobenzene-linked cholesterol derivative with p-NMe(2)) is frequently inverted. After careful examination of the gel preparation conditions, we found that inversion takes place only when the cooling speed is fast. The scanning electron microscopic studies established that gelators form three-dimensional networks with helical fibrils. Interestingly, we found that in the 3Me' gel prepared from cyclohexane the gel with (R)-chirality in CD possesses a right- handed helix whereas the gel with (S)-chirality in the CD possesses a left-handed helix. The sol-gel phase transition was also induced by photoresponsive cis-trans isomerism of the azobenzene moiety: the gel formed from the trans-isomer was efficiently converted to the sol when trans-to-cis isomerization was photochemically induced, and this process can be repeated reversibly. The photoinduced sol-gel phase transition was also ''read-out'' as a change in CD spectroscopy.
• SHINKAI SEIJI; SHIGEMATSU KAZUYOSHI; OGAWA TOSHIYUKI; MINAMI TAKAHIDE; MA+, TETRAHEDRON LETT., 1980, 21, NO 46, 4463-4466
  作者：SHINKAI SEIJI、 SHIGEMATSU KAZUYOSHI、 OGAWA TOSHIYUKI、 MINAMI TAKAHIDE、 MA+

  DOI：——

  日期：——