3,3'-bis(bromomethyl)azobenzene | 93824-64-7

• 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: 3,3'-bis(bromomethyl)azobenzene
• 英文别名: (1E)-1,2-bis[3-(Bromomethyl)phenyl]-diazene；bis[3-(bromomethyl)phenyl]diazene
• CAS: 93824-64-7
• 化学式: C₁₄H₁₂Br₂N₂
• 分子量: 368.071
• InChiKey: MIQFQSNNPFQSRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3'-bis(bromomethyl)azobenzene 在 sodium hydroxide 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 disodium (E)-5,5′-(((diazene-1,2-diyl)bis(3,1-phenylene)bis-(methylene))bis(oxy))bis(4-oxo-4H-chromene-2-carboxylate)
  参考文献：
  名称：

  Design, Synthesis, and Inhibitory Activity of Potent, Photoswitchable Mast Cell Activation Inhibitors

  摘要：

  Allergic reactions affect millions of people worldwide. The need for new and effective antiallergic agents is evident, and insight into the underlying mechanisms that lead to allergic events is necessary. Herein, we report the design, synthesis, and activity of photoswitchable mast cell activation inhibitors. In mast cell degranulation assays, these inhibitors possess significantly greater potency than an original, chromone-based antiallergic agent. Furthermore, one of the photoswitchable inhibitors shows a significant difference in inhibitory activity between its two photoisomeric forms. Further optimization could ultimately lead to a photoswitchable compound suitable for studying mechanisms involved in allergic reactions in a novel manner, with activity addressable by light and with precise spatiotemporal control over events at the molecular level.

  DOI：

  10.1021/jm400115k
• 作为产物：
  描述：

  3-硝基甲苯 在 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 作用下， 以 四氯化碳 、 乙醚 、 苯 为溶剂， 反应 60.0h， 生成 3,3'-bis(bromomethyl)azobenzene
  参考文献：
  名称：

  套索醚的电化学开关。中性和还原形式的单臂和双臂碳和氮枢轴套索醚的阳离子结合调查

  摘要：

  Determination du comportement electronique de 14 systemesaromatiques deficients en electrons, par voltammetrie cyclique, en missing et en存在 de Li + , Na + et K + 。Les 支持包括 des ethers lariats a pivot-azote et -carbone、des podands nitroaromatiques、des ethers nitroaromatiques simples et des azocryptands。Les lariat a pivot-carbone sont des ethers fix au groupemethyle du 2-methyl-15-crown-5 ou du -18-crown-6

  DOI：

  10.1021/ja00293a027

文献信息

• Light-triggered self-assembly of a dichromonyl compound in water
  作者：Willem A. Velema、Marc C. A. Stuart、Wiktor Szymanski、Ben L. Feringa

  DOI：10.1039/c3cc41018h

  日期：——

  External control over self-assembling structures is achieved by incorporating an azobenzene photoswitch into the structure of a dichromonyl compound. The self-assembly of dichromonyl compounds into fibers leads to the formation of a hydrogel and can be triggered with visible light.

  通过将偶氮苯光开关嵌入二聚体化合物的结构中，实现了对自组装结构的外部控制。二聚体化合物自组装成纤维，从而形成水凝胶，并可通过可见光触发。
• [EN] NOVEL BIS-CHROMONE DERIVATIVES, METHODS FOR THEIR PREPARATION AND USES THEREOF<br/>[FR] NOUVEAUX DÉRIVÉS DE BIS-CHROMONE, LEURS PROCÉDÉS DE PRÉPARATION ET UTILISATIONS
  申请人：UNIV GRONINGEN

  公开号：WO2014098597A1

  公开（公告）日：2014-06-26

  The invention relates to novel bis-chromone derivatives, methods for their preparation and their therapeutic application, especially in the treatment or prevention of disease involving mast cell activation, such as allergic disease. Provided is a compound according to the general Formula (I).

  这项发明涉及新型双咖啡因衍生物，其制备方法及其治疗应用，特别是在涉及肥大细胞活化的疾病的治疗或预防中，如过敏性疾病。提供的是符合一般式（I）的化合物。
• Azobenzene-bridged calix[8]arenes
  作者：Grazia M.L. Consoli、Corrada Geraci、Placido Neri、Giacomo Bergamini、Vincenzo Balzani

  DOI：10.1016/j.tetlet.2006.08.067

  日期：2006.10

  An azobenzene bridge was introduced into the lower (or smaller) rim of p-tert-butylcalix[8]arene (1) and 1,5-calix[8]crown-3 (2) to form 1,4-singly bridged (3) and 1,5:3,7-doubly bridged (4) calix[8]arene derivatives, respectively. Trans and cis isomers of conformationally rigid 4 were isolated. The quantum yields of the trans–cis photoisomerisation reactions have been measured.

  将偶氮苯桥引入对-叔丁基杯[8]芳烃（1）和1,5-杯[8]冠-3（2）的下（或更小）边缘，以形成1,4-单桥（3）和1,5：3,7双桥（4）杯[8]芳烃衍生物。分离出构象刚性为4的反式和顺式异构体。反式-顺式光异构化反应的量子产率已被测量。
• A Photoswitchable Metallocycle Based on Azobenzene: Synthesis, Characterization, and Ultrafast Dynamics
  作者：Raphael I. Petrikat、Justin Hornbogen、Marcel J. P. Schmitt、Emma Resmann、Christina Wiedemann、Nesrin I. Dilmen、Heinrich Schneider、Annika M. Pick、Christoph Riehn、Rolf Diller、Sabine Becker

  DOI：10.1002/chem.202400205

  日期：——

  An azobenzene based Cu(I) metallocycle constituting the prototype for reversibly photoswitchable (3d

  一种基于偶氮苯的 Cu(I) 金属环，构成可逆光开关 (3d
• Bauer, Martin; Mueller, Walter Manfred; Mueller, Ute, Liebigs Annalen, 1995, # 4, p. 649 - 656
  作者：Bauer, Martin、Mueller, Walter Manfred、Mueller, Ute、Rissanen, Kari、Voegtle, Fritz

  DOI：——

  日期：——