4-[(4-bromobutoxyphenyl)azo]azobenzoic acid | 136954-87-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 4-[(4-bromobutoxyphenyl)azo]azobenzoic acid
• 英文别名: p-[p-(4-bromobutoxy)phenylazo]benzoic acid；4-((bromobutyloxyphenyl)azo)benzoic acid；4-(n-bromobutoxyphenyl)azobenzoic acid
• CAS: 136954-87-5
• 化学式: C₁₇H₁₇BrN₂O₃
• 分子量: 377.238
• InChiKey: ZDQOWEBGPDDUSB-FMQUCBEESA-N

物化性质

• 沸点：
  550.3±40.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  71.25
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-[(4-bromobutoxyphenyl)azo]azobenzoic acid 在 4-二甲氨基吡啶 、 sodium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 生成 4-(2-aminoethylamino)butoxy-4'-[(cholesteryloxy)carbonyl]azobenzene
  参考文献：
  名称：

  Jung, Jong Hwa; Shinkai, Seiji, Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 12, p. 2393 - 2398

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4-二溴丁烷 、 4-[2-(4-hydroxyphenyl)diazen-1-yl]benzoic acid 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以15%的产率得到4-[(4-bromobutoxyphenyl)azo]azobenzoic acid
  参考文献：
  名称：

  Organic gels are useful as a template for the preparation of hollow fiber silica

  摘要：

  采用有机凝胶纤维作为模板，制备了一种具有管状结构的介孔二氧化硅新材料。

  DOI：

  10.1039/a802829j

文献信息

• MOLECULES, COMPOSITIONS, AND METHODS FOR LIGHT ABSORPTION
  申请人：Wang Jinye

  公开号：US20140193348A1

  公开（公告）日：2014-07-10

  Embodiments provided herein relate to molecules, compositions, and methods for light absorption. In some embodiments, the molecules and/or compositions can be used to absorb ultraviolet light. In some embodiments, the ultraviolet light absorption compound can be used in a sunscreen composition. In some embodiments, the compound includes an azobenzene group for the absorption of ultraviolet light.

  本文提供的实施例涉及分子、组合物和用于光吸收的方法。在某些实施例中，这些分子和/或组合物可用于吸收紫外光。在某些实施例中，紫外光吸收化合物可用于防晒霜组合物中。在某些实施例中，该化合物包括偶氮苯基团用于吸收紫外光。
• [EN] AZOBENZENE COMPOUNDS WITH CHOLESTEROL GROUP AND THEIR SUNSCREEN COMPOSITIONS<br/>[FR] COMPOSÉS AZOBENZÉNIQUES AVEC GROUPE CHOLESTÉROL ET COMPOSITIONS ANTISOLAIRES ASSOCIÉES
  申请人：EMPIRE TECHNOLOGY DEV LLC

  公开号：WO2013123658A1

  公开（公告）日：2013-08-29

  Provided are azobenzene compounds with cholesterol group of the following formula, wherein n=l or 2 and R3 is either no substitution or a phenyl group. Sunscreen compositions comprising said azobenzene compounds are also provided. Formula (I).

  提供具有胆固醇基团的偶氮苯化合物，其具有以下公式，其中n=1或2，R3要么没有取代基，要么是一个苯基。还提供了包含所述偶氮苯化合物的防晒组合物。公式（I）。
• Creation of Double Silica Nanotubes by Using Crown-Appended Cholesterol Nanotubes
  作者：Jong Hwa Jung、Seok-Hoon Lee、Jong Shin Yoo、Kaname Yoshida、Toshimi Shimizu、Seiji Shinkai

  DOI：10.1002/chem.200305008

  日期：2003.11.7

  right-handed helical motif. Since the exciton coupling band of the organogel also shows P (right-handed) helicity, we consider that a microscopic helicity is reflected by a macroscopic helicity. On the other hand, the tubular structure of the silica obtained from the organogels 2 and 3 is somewhat different from that prepared from the organogel 1. The careful examination of SEM and TEM pictures revealed

  合成了新的基于冠的胆固醇基有机胶凝剂1-3，该化合物具有一个或两个胆固醇骨架作为手性聚集体形成位点，两个氨基作为酸性质子结合位点和一个冠状部分作为阳离子结合位点，并在有机溶剂中评价凝胶化能力。这些胶凝剂可以使1.0重量％以下的几种有机溶剂胶凝，表明1-3充当各种有机溶剂的通用胶凝剂。我们观察到1-3的乙酸或丙酸凝胶的CD光谱，以表征有机凝胶系统中的聚集模式。在乙酸凝胶1的CD光谱中，第一个棉花效应的正号表示偶氮苯生色团的偶极矩趋向于顺时针方向。另一方面，丙酸凝胶2和3 仅含一个胆固醇的部分对第一棉效应显示负号，强烈表明偶氮苯生色团的偶极矩朝向逆时针方向。1+乙酸凝胶的TEM图像显示出螺旋带状和管状结构。在凝胶相中以1-3作为模板进行四乙氧基硅烷（TEOS）的溶胶-凝胶缩聚。由1+乙酸凝胶获得的二氧化硅显示出具有200-1700nm宽度的螺旋带和具有恒定约560nm外径的二氧化硅的管状结构。
• Organogels are useful as a template for the preparation of novel helical silica fibers
  作者：Yoshiyuki Ono、Kazuaki Nakashima、Masahito Sano、Junichi Hojo、Seiji Shinkai

  DOI：10.1039/b102550n

  日期：——

  Sol–gel polymerization of tetraethoxysilane (TEOS) was carried out in the organogel phase consisting of cholesterol-based gelators (neutral 1 and cationic 2). TEOS polymerization in neutral 1 + MeCO2H gel resulted in the conventional granular silica whereas that in cationic 2 + MeCO2H gel yielded the novel mesoporous silica with a tubular structure. SEM and TEM observations and additive effects established that the organogel fibers act as a template in the TEOS polymerization process to yield the hollow silica fibers and that the electrostatic interaction plays a crucial role in adsorption of anionic oligomeric silica particles onto the cationic organogel fiber surface. Thus, the tubular structure is created after combustion of the gelators by calcination. Very interestingly, when TEOS polymerization was carried out in the 1 + 2 mixed organogel, fibrous silica with a right-handed “helical” structure was created. This phenomenon appeared only in the range of 2/(1 + 2) = 5–15 mol%. Since the higher-order helical structure is characteristic of supramolecular assemblies of “chiral” organic compounds, it is suggested that the chirality in the organogel fibers is successfully transcribed into the inorganic silica fibers. Thus, the concept presented in this paper describes a novel template effect and should be broadly applicable to the design of “supramolecular” silica materials useful for catalysts, memory storage, replication, etc.

  在基于胆固醇的凝胶剂（中性1和阳离子2）组成的疏水凝胶相中进行了四乙氧基硅烷（TEOS）的溶胶-凝胶聚合反应。在中性1 + MeCO2H凝胶中进行的TEOS聚合反应得到了传统的颗粒状二氧化硅，而在阳离子2 + MeCO2H凝胶中则得到了具有管状结构的新型介孔二氧化硅。扫描电镜和透射电镜观察以及添加剂效应表明，有机凝胶纤维在TEOS聚合过程中起到了模板作用，生成了空心二氧化硅纤维，并且静电相互作用在阴离子寡聚二氧化硅颗粒吸附到阳离子有机凝胶纤维表面方面起着至关重要的作用。因此，通过煅烧燃烧凝胶剂后形成了管状结构。非常有趣的是，当在1 + 2混合有机凝胶中进行TEOS聚合时，产生了具有右旋“螺旋”结构的纤维状二氧化硅。这种现象仅在2/(1 + 2) = 5–15 mol%的范围内出现。由于高级螺旋结构是有机“手性”化合物的超分子组装的特征，因此可以认为有机凝胶纤维中的手性成功地传递给了无机二氧化硅纤维。因此，本文提出的概念描述了一种新颖的模板效应，并且应广泛适用于设计可用于催化剂、存储、复制等的“超分子”二氧化硅材料。
• Helical Ribbon Aggregate Composed of a Crown-Appended Cholesterol Derivative Which Acts as an Amphiphilic Gelator of Organic Solvents and as a Template for Chiral Silica Transcription
  作者：Jong Hwa Jung、Hedeki Kobayashi、Mitsutoshi Masuda、Toshimi Shimizu、Seiji Shinkai

  DOI：10.1021/ja010508h

  日期：2001.9.1

  New crown-appended cholesterol-based organogelator 1, which has two cholesterol skeletons as a chiral aggregate-forming site, two amino groups as an acidic proton-binding site, and one crown moiety as a cation-binding site, was synthesized, and the gelation ability was evaluated in organic solvents, It can gelate acetic acid, acetonitrile, acetone, ethanol, 1-butanol, 1-hexanol, DMSO, and DMF under 1.0 wt %, indicating that 1 acts as a versatile gelator of various organic solvents. To characterize the aggregation mode in the organogel system, we observed a CD spectrum of the acetic acid gel 1. In the CD spectrum, the lambda (theta =0) value appears at 353 nm, which is the same as the absorption maximum lambda (max) = 353 nm. The positive sign for the first Cotton effect indicates that the dipole moments of azobenzene chromophores tend to orient in a clockwise direction. Very surprisingly, the TEM images of the 1 + acetic acid gel resulted in the helical ribbon and the tubular structures. Sol-gel polymerization of tetraethoxysilane was carried out using 1 in the gel phase. The silica obtained from the 1 + acetic acid gel showed the helical ribbon with 1700-1800-nm pitches and the tubular structure of the silica with similar to 560-nm outer diameter. As far as can be recognized, all the helicity possesses a right-handed helical motif. Since the exciton-coupling band of the organogel also shows R (right-handed) helicity, we consider that a microscopic helicity is reflected by a macroscopic helicity.