2-bromo-5-iodo-1,4-dihydroxybenzol | 216306-47-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-bromo-5-iodo-1,4-dihydroxybenzol
• 英文别名: 1-bromo-4-iodohydroquinone；2-bromo-5-iodohydroquinone；4-Bromo-2,5-dihydroxyiodobenzene；2-bromo-5-iodobenzene-1,4-diol
• CAS: 216306-47-7
• 化学式: C₆H₄BrIO₂
• 分子量: 314.905
• InChiKey: RFLSZEHDGVCXNR-UHFFFAOYSA-N

物化性质

• 熔点：
  165.4 °C (decomp)(Solv: methanol (67-56-1))
• 沸点：
  288.5±40.0 °C(Predicted)
• 密度：
  2.528±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-5-iodo-1,4-dihydroxybenzol 在 四(三苯基膦)钯 、 18-冠醚-6 、 三正丁胺 、 palladium diacetate 、 potassium carbonate 、 三(邻甲基苯基)磷 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 108.0h， 生成
  参考文献：
  名称：

  Chemical Molecule-Induced Light-Activated System for Anticancer and Antifungal Activities

  摘要：

  Except for chemotherapy, surgery, and radiotherapy, photodynamic therapy (PDT) as new therapy modality is already in wide clinic use for the treatment of various diseases. The major bottleneck of this technique is the requirement of outer light source, which always limits effective application of PDT to the lesions in deeper tissue. Here, we first report a new modality for treating cancer and microbial infections, which is activated by chemical molecules instead of outer light irradiation. In this system, in situ bioluminescence of luminol can be absorbed by a cationic oligo(p-phenylene vinylene) (OPV) that acts as the photosensitizer through bioluminescence resonance energy transfer (BRET) process. The excited OPV sensitizes oxygen molecule in the surroundings to produce reactive oxygen species (ROS) that kill the adjacent cancer cells in vitro and in vivo, and pathogenic microbes. By avoiding the use of light irradiation, this work opens a new therapy modality to tumor and pathogen infections.

  DOI：

  10.1021/ja304986t
• 作为产物：
  描述：

  4-n-propoxyphenyl acetate 在 硫酸 、 水 、 溴 、 碘 、 sodium acetate 、 三溴化硼 、 碘酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 、 丙酮 为溶剂， 反应 24.0h， 生成 2-bromo-5-iodo-1,4-dihydroxybenzol
  参考文献：
  名称：

  2-Bromo-5-iodo-hydroquinone 及其对称和不对称二烷基醚

  摘要：

  2-溴-5-碘-氢醌二烷基醚是通过氢醌单烷基醚的逐步卤化和烷基化使用简单易行的反应制备的。三溴化硼诱导的二丙酰基醚裂解以良好的产率得到母体化合物 2-溴-5-碘-氢醌。

  DOI：

  10.1515/znb-1998-0905

文献信息

• Symmetrical or non-symmetrical luminescent turnstiles based on hydroquinone stators and rotors bearing pyridyl or p-dimethylaminopyridyl coordinating units
  作者：Bérangère Godde、Abdelaziz Jouaiti、Audrey Fluck、Nathalie Kyritsakas、Matteo Mauro、Mir Wais Hosseini

  DOI：10.1039/c7dt02762a

  日期：——

  Et4NBr. For the symmetric turnstiles T1 and T2, bearing two pyridyl units on the stator, the binding of the Ag+ cation leads to an oscillating phenomenon between the two energetically equivalent closed states. However, in the case of turnstile T1, the oscillating process could be prevented by blocking the rotational movement using PdCl2 as the locking agent. Owing to the emissive nature of the stator

  设计并合成了一种新型的分子旋转栅T1-T5。所有五个旋转栅均基于共价互连的定子和转子。虽然旋转栅门T1-T2是基于对称定子，该定子配备有两个配位吡啶基单元，并且转子带有吡啶基或对二甲氨基吡啶基配位基团，但两个非对称旋转栅门T4和T5是基于仅包含一个吡啶基的定子的单元和与上述T1和T2相同的转子。通过金属阳离子在旋转门的打开状态（T1-T5）和闭合状态（TM）之间进行切换（M = Ag +使用1D和2D NMR技术研究溶液中的Pd 2+或Pd 2+）。通过添加Ag +阳离子通过同时结合定子和转子的两个吡啶基部分，实现了导致旋转门关闭状态的旋转运动的锁定。通过添加Et 4 NBr实现了回到打开状态的解锁过程。对于在定子上带有两个吡啶基单元的对称旋转门T1和T2，Ag +阳离子的结合会导致在两个能量等效的闭合状态之间产生振荡现象。但是，在旋转闸门T1的情况下通过使用PdCl 2作为锁定剂来阻止旋
• Shape-persistent V-shaped mesogens—formation of nematic phases with biaxial order
  作者：Matthias Lehmann、Shin-Woong Kang、Christiane Köhn、Sönke Haseloh、Ute Kolb、Dieter Schollmeyer、QingBing Wang、Satyendra Kumar

  DOI：10.1039/b605718g

  日期：——

  A homologous series of shape-persistent V-shaped molecules has been designed to form the biaxial nematic phase. Phenyleneethynylene moieties are attached to a bent fluorenone unit to create an apex angle of about 90°, which is determined from the single crystal structure. Two mesogens, one symmetric and another unsymmetric, have been synthesized by attaching a cyano group to one or both of the peripheral phenyl units, respectively. These groups introduce local dipoles essential for the formation of the nematic phases. The tendency to form a crystalline phase is reduced by laterally substituted hexyloxy chains which allow the nematic phase to be supercooled to a glassy state. Two of the three fluorenone derivatives exhibit a transition from the uniaxial nematic to the biaxial nematic phase. This transition has an undetectably small transition enthalpy, but the X-ray diffraction, polarizing optical microscopy, and conoscopy reveal the presence of the biaxial order in the low temperature nematic phase.

  一种同源系列的形状持久的V型分子已被设计为形成双轴向列相。通过将苯乙炔基团连接到弯曲的菲啰酮单元，创建了一个约90°的顶角，该角度是通过单晶结构确定的。合成了两种介质，其中一种是对称的，另一种是非对称的，分别是通过将硝基团连接到一个或两个外周苯基单元来实现的。这些基团引入了形成向列相所必需的局部偶极子。侧面取代的己氧链减少了形成晶相的倾向，使得向列相可以超冷至玻璃态。三种菲啰酮衍生物中，有两种表现出从单轴向列相到双轴向列相的过渡。这个过渡具有不可检测的小过渡焓，但X射线衍射、偏振光学显微镜和光度计显示在低温向列相中存在双轴有序。
• Oligomers and Cyclooligomers of Rigid Phenylene-Ethynylene-Butadiynylenes: Synthesis and Self-Assembled Monolayers
  作者：Stefan-S. Jester、Natalia Shabelina、Stephan M. Le Blanc、Sigurd Höger

  DOI：10.1002/anie.201001625

  日期：2010.8.16

  different reaction conditions (palladium or copper catalysis) selectively yielded cyclic or acyclic oligomers with n=2–6 (see picture for n=3) linked by freely rotating corner units. STM images of self‐assembled monolayers revealed the difference in the adsorption behavior of the acyclic and cyclic oligomers.

  从相同的双乙炔开始，不同的反应条件（钯或铜催化）有选择地产生n = 2–6（参见图片中的n = 3）的环状或非环状低聚物，其通过自由旋转的角单元连接。自组装单层的STM图像显示了无环和环状低聚物的吸附行为的差异。
• Molecular Wire Effects in Phenyleneethynylene Oligomers: Surprising Insights
  作者：Marcel Hergert、Markus Bender、Kai Seehafer、Uwe H. F. Bunz

  DOI：10.1002/chem.201705604

  日期：2018.3.2

  The synthesis and quenching behavior of a series of water‐soluble, carboxylate‐carrying phenyleneethynylene oligomers—monomer to tetramer—and their polymers are reported; their quenching behavior with different test analytes (paraquat, lead salts, mercury salts, picric acid, methylpyridinium iodide) in water were investigated, and the results were compared to that of the conjugated polymer. Significant

  报道了一系列水溶性的，携带羧酸盐的亚苯基亚乙炔基低聚物（对四聚体的单体）及其聚合物的合成和猝灭行为；研究了它们在水中的不同测试分析物（百草枯，铅盐，汞盐，苦味酸，甲基吡啶碘化物）的猝灭行为，并将结果与​​共轭聚合物进行了比较。发现了显着但依赖分析物的增强作用。对于单价淬灭剂，仅适用分子键效应，但对于二价淬灭剂，多价效应也很重要。
• Huenig, Siegfried; Bau, Robert; Kemmer, Martina, European Journal of Organic Chemistry, 1998, # 2, p. 335 - 348
  作者：Huenig, Siegfried、Bau, Robert、Kemmer, Martina、Meixner, Hubert、Metzenthin, Tobias、et al.

  DOI：——

  日期：——