5-amino-2-(2'-hydroxy-4'-methylphenyl)benzoxazole | 1005003-21-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-amino-2-(2'-hydroxy-4'-methylphenyl)benzoxazole
• 英文别名: 5-amino-2-(2-hydroxy-4-methylphenyl)benzoxazole；2-(5-Amino-1,3-benzoxazol-2-yl)-5-methylphenol
• CAS: 1005003-21-3
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: KVRPNJULNLEHIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  72.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-amino-2-(2'-hydroxy-4'-methylphenyl)benzoxazole 、 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl (4-((2-(2-hydroxy-4-methylphenyl)benzo[d]oxazol-5-yl)amino)-4-oxobutyl)carbamate
  参考文献：
  名称：

  Synthesis of organogelling, fluoride ion-responsive, cholesteryl-based benzoxazole containing intra- and intermolecular hydrogen-bonding sites

  摘要：

  A cholesteryl-based 2-(2'-hydroxyphenyl)benzoxazole (HPB) derivative 3 linked with an amide bond was prepared through an efficient synthetic pathway. The HPB, amide, and cholesteryl groups play important roles in constructing the supramolecular gel structure. UV-vis and fluorescence spectroscopy also showed that HPB and amide groups, which provide intra- and intermolecular hydrogen bonding, respectively, also contribute the recognition of fluoride anions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.053
• 作为产物：
  描述：

  4-甲基水杨酸 、 2,4-diaminophenol dihydrochloride 在 polyphosphoric acid 作用下， 反应 12.0h， 以26%的产率得到5-amino-2-(2'-hydroxy-4'-methylphenyl)benzoxazole
  参考文献：
  名称：

  含2-（2'-羟基苯基）苯并恶唑的可逆荧光有机凝胶的合成：凝胶化后的荧光增强和神经气体模拟物的检测性能

  摘要：

  通过与5-氨基-2-（2'-羟基-4'-甲基苯基）苯并恶唑与5-氨基-2-（2'-羟基-4'-甲基苯基）苯并恶唑反应，合成了一种新的含有2-（2'-羟基苯基）苯并恶唑（HPB）基团的低分子有机胶凝剂1。室温下在THF中的异氰酸十二烷基酯。的可逆凝胶化能力1在各种有机溶剂中使用加热-冷却方法进行了研究。稳定的有机凝胶是由四氯化碳或环己烷以低至0.9％的浓度形成的。由非共价键形成的自组装超分子凝胶结构通过场发射扫描电子显微镜（FE-SEM）证实，根据所使用的溶剂，其呈现原纤维或带状结构。关于聚集诱导的发射增强（AIEE）现象，在其溶液和胶凝状态下研究了光学性质。紫外可见光谱和荧光光谱法监测了所得有机凝胶对神经气体模拟物的检测特性。

  DOI：

  10.1016/j.tet.2010.01.006

文献信息

• Self-Assembly of Supramolecualr Metallogelator Containing 2-(2′-Hydroxyphenyl) benzoxazole/Zn(II) Chelate
  作者：Tae Hyeon Kim、Na Young Kwon、Ji Hye Son、Changduk Yang、Minjung Lee、Taek Seung Lee

  DOI：10.1166/jnn.2010.2972

  日期：2010.10.1

  A low molar mass organogelator 1 containing 2-(2′-hydroxyphenyl)benzoxazole (HPB) unit with long alkyl chain was synthesized by the reaction with HPB and octyl isocyanate in THF at room temperature. A new chelate-based organogelator 1-Zn(II) was prepared with the reaction of 1 and zinc(II) acetate in methanol and dichloromethane at mild condition. The gelation ability of organogelator was tested by heating–cooling method in various organic solvents, and the opaque gel was formed from DMF. Well-developed self-assembled structure of organogel was confirmed with field emission-scanning electron microscope (FE-SEM) and transmission electron microscope (TEM), and the optical properties of organogel upon aggregation were monitored by UV-Vis and fluorescence spectroscopy. 1-Zn(II) was self-assembled to the sheet-like structure with the thickness of fully extended length of molecules.

  合成了一种低摩尔质量的有机凝胶剂1，包含长烷基链的2-(2′-羟基苯基)苯并噁唑（HPB）单元，采用HPB与辛基异氰酸酯在室温下于四氢呋喃（THF）中反应制得。通过在温和条件下用甲醇和二氯甲烷对1与乙 acetate 反应，制备了新的以螯合物为基础的有机凝胶剂1-Zn(II)。在各种有机溶剂中通过加热-冷却法测试了有机凝胶剂的凝胶能力，并且从DMF中形成了不透明的凝胶。用场发射扫描电子显微镜（FE-SEM）和透射电子显微镜（TEM）确认了有机凝胶的自组装结构良好发展，结合光谱法监测了有机凝胶在聚集过程中的光学特性。1-Zn(II)自组装成片状结构，厚度为分子的完全延伸长度。
• Fluorescence resonance energy transfer between polydiacetylene vesicles and embedded benzoxazole molecules for pH sensing
  作者：Seongwon Seo、Daigeun Kim、Geunseok Jang、Dong-Myung Kim、Dong Wook Kim、Bum-Kyoung Seo、Kune-Woo Lee、Taek Seung Lee

  DOI：10.1016/j.reactfunctpolym.2012.11.016

  日期：2013.3

  A mixed polydiacetylenes (PDAs) vesicle with a phospholipid unit is functionalized by entrapping fluorescent benzoxazole (BZ) molecules inside the PDA vesicles. Upon photo-polymerization and heat-treatment of the self-assembled vesicles, a weak red fluorescence can be observed. Excitation of BZ molecules enables the amplification of PDA vesicle fluorescence resonance energy transfer (FRET) to more than four times that of the direct excitation of red-phase PDA vesicles. The backbone of the PDA vesicles act as energy acceptors, which absorb energy from embedded BZ donor molecules inside the PDA vesicle, which emit blue fluorescence. The amplified red emission from the PDA vesicle can be altered by pH changes in the aqueous solution and thus the PDA vesicle mixed with a phospholipid and entrapped molecules inside can be a promising candidate as a pH sensor. (C) 2012 Elsevier Ltd. All rights reserved.