N-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl)azo-4-phenol | 77100-96-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl)azo-4-phenol
• 英文别名: p-[4'-(benzo-15-crown-5)azo]phenol；4'-(4-hydroxyphenylazo)benzo-15-crown-5；p-[4'-(benzo-15-crown-5-ether)azo]phenol
• CAS: 77100-96-0
• 化学式: C₂₀H₂₄N₂O₆
• 分子量: 388.42
• InChiKey: NFENEEAOGQFVOE-QURGRASLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  91.1
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl)azo-4-phenol 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-铌苯基15-5-乙基 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl)azo-4-phenol
  参考文献：
  名称：

  Synthesis and Photoswitchable Complexation/Extraction Properties of Lipophilic Azabis(benzo-15-crown-5) Ionophores for Alkali Metal Cations

  摘要：

  Novel lipophilic derivatives of azobis(benzo-15-crown-5) (1b, 1c) were synthesized and their photoisomerization, complexation and extraction properties for alkali metal cations were investigated. Upon UV light irradiation, the photostationary state of the trans and cis isomers was reached and, with both 1b and 1c, the extractabilities of Rb+ and Cs+ increased due to the formation of 1:1 sandwich-type complexes by the cis isomers. On the other hand, the extractability of K+ decreased, possibly because the 2:1 complexes formed by the trans isomers are more stable and/or lipophilic than the complexes of the cis isomers.

  DOI：

  10.3987/com-97-s(n)87

文献信息

• Guest-induced supramolecular chirality in a ditopic azoprobe–cyclodextrin complex in water
  作者：Kentaro Nonaka、Mai Yamaguchi、Masashi Yasui、Shoji Fujiwara、Takeshi Hashimoto、Takashi Hayashita

  DOI：10.1039/c4cc04227a

  日期：——

  The novel supramolecular sensors induced by the clockwise twisted structures due to multi-point recognition in water.

  由于多点识别在水中引起顺时针扭曲结构，产生了新型超分子传感器。
• Structural Effect of Amphiphilic Crown Ether Azoprobes on Alkali Metal Ion Recognition and Aggregation Behavior in Water
  作者：Fuyuki Sato、Miki Tsukano、Koki Sakamoto、Wakako Umemoto、Takeshi Hashimoto、Takashi Hayashita

  DOI：10.1246/bcsj.81.1589

  日期：2008.12.15

  Amphiphilic azoprobes having a crown ether moiety (15C5–Azo–Cn; n=4, 6, 8, and 12 and 18C6–Azo–Cn; n=4, 6, and 8) were synthesized. We examined the effect of alkyl spacer length of the amphiphilic ...

  合成了具有冠醚部分（15C5–Azo–Cn；n=4、6、8 和 12 和 18C6–Azo–Cn；n=4、6 和 8）的两亲性偶氮探针。我们检查了两亲分子的烷基间隔长度的影响...
• Self-assembly of Amphiphilic Benzo-15-crown-5 Azoprobes in Response to Alkali Metal Ions in Water
  作者：Fuyuki Sato、Kouki Sakamoto、Wakako Umemoto、Takeshi Hashimoto、Takashi Hayashita

  DOI：10.1246/cl.2007.880

  日期：2007.7.5

  The amphiphilic benzo-15-crown-5 (B15C5) azoprobes exhibit a self-assembly in response to alkali metal ions in water based on the exciton interaction of the phenylazo groups in the probes, and the most selective response to K + was obtained for an azoprobe possessing a hexyl spacer unit.

  基于探针中苯基偶氮基团的激子相互作用，两亲性苯并-15-冠-5（B15C5）偶氮探针表现出响应水中碱金属离子的自组装，并且获得了对 K + 最具选择性的响应具有己基间隔单元的偶氮探针。
• Potassium Ion Selective Signaling Based on Intramolecular Dimer Formation of Biscrown Ether Azochromophore —Chemosensor Exhibiting Forceps Function—
  作者：Takashi Hayashita、Akiko Murakami、Norio Teramae

  DOI：10.1246/cl.2004.568

  日期：2004.5

  A novel bisbenzo-15-crown-5 azochromophore, 2, which exhibits forceps function, has been designed. 2 shows selective UV–vis spectral response for K+ in acetonitrile, which is based on the exciton interaction of the two azochromophores upon forming an intramolecular sandwich complex with K+.

  我们设计了一种新型双苯并-15-冠-5 偶氮色团 2，它具有镊子功能。2 在乙腈中对 K+ 显示出选择性紫外-可见光谱响应，这是基于两个偶氮色团与 K+ 形成分子内夹心复合物时的激子相互作用。
• Akabori, Sadatoshi; Miura, Yoshikazu; Yotsumoto, Noriko, Journal of the Chemical Society. Perkin transactions I, 1995, # 20, p. 2589 - 2594
  作者：Akabori, Sadatoshi、Miura, Yoshikazu、Yotsumoto, Noriko、Uchida, Kiyoshi、Kitano, Masaru、Habata, Yoichi

  DOI：——

  日期：——