2,5-bis(bromomethyl)benzoate | 148692-73-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,5-bis(bromomethyl)benzoate
• 英文别名: Ethyl 2,5-bis(bromomethyl)benzoate
• CAS: 148692-73-3
• 化学式: C₁₁H₁₂Br₂O₂
• 分子量: 336.023
• InChiKey: WZROPXLJBQDEPO-UHFFFAOYSA-N

物化性质

• 沸点：
  393.8±42.0 °C(Predicted)
• 密度：
  1.656±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-bis(bromomethyl)benzoate 在 sodium hydroxide 、 氯化亚砜 、 sodium ethanolate 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 苯 为溶剂， 反应 28.0h， 生成
  参考文献：
  名称：

  基于α-酮酸基序的二齿蛋白酪氨酸磷酸酶抑制剂库的并行合成。

  摘要：

  蛋白质酪氨酸磷酸酶（PTPases）通过控制细胞中酪氨酸磷酸化水平来调节细胞内信号转导途径。这些酶在包括II型糖尿病和鼠疫耶尔森菌（鼠疫是鼠疫的致病菌）感染在内的多种疾病中起着重要作用。该报告描述了使用并行溶液相方法合成104种PTPase潜在抑制剂的文库。库成员基于双（芳基α-酮羧酸）基序，该基序在中央苯接头上结合了羧酸。该羧酸通过酰胺键与多种不同的芳族胺偶联。设计所得酰胺的芳族成分以使其与围绕PTPase活性位点的残基接触。针对耶尔森氏菌PTPase和PTP1B筛选了该文库。根据筛选结果，选择了该库的四个成员进行进一步研究。对这四种化合物针对耶尔森氏菌PTPase，PTP1B，TCPTP，CD45和LAR进行了评估。化合物14对PTP1B的IC（50）值为590nM，是可逆的竞争性抑制剂。这种亲和力表示效力比化合物2（文库所基于的母体结构）高120倍以上。第二种抑制剂化合物12对耶尔森

  DOI：

  10.1016/j.bmc.2004.03.058
• 作为产物：
  描述：

  2,5-二甲基苯甲酸 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 硫酸 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 生成 2,5-bis(bromomethyl)benzoate
  参考文献：
  名称：

  Simple Mechanical Molecular and Supramolecular Machines: Photochemical and Electrochemical Control of Switching Processes

  摘要：

  AbstractPhotochemical control of a self‐assembled supramolecular 1:1 pseudorotaxane (formed between a tetracationic cyclophane, namely the tetrachloride salt of cyclobis(paraquat‐p‐phenylene), and 1,5‐bis[2‐(2‐(2‐hydroxy)ethoxy)ethoxy]naphthalene) has been achieved in aqueous solution. The photochemical one‐electron reduction of the cyclophane to the radical trication weakens the noncovalent bonding interactions between the cyclophane and the naphthalene guest—π‐π interactions between the π‐electron‐rich and π‐electron‐poor aromatic systems, and hydrogen‐bonding interactions between the acidic α‐bipyridinium hydrogen atoms of the cyclophane and the polyether oxygen atoms of the naphthalene derivative—sufficiently to allow the guest to dethread from the cavity; the process can be monitored by the appearance of naphthalene fluorescence. The radical tricationic cyclophane can be oxidized back to the tetracation in the dark by allowing oxygen gas into the system. This reversible process is marked by the disappearance of naphthalene fluorescence as the molecule is recomplexed by the tetracationic cyclophane. This supramolecular system can be chemically modified such that the π‐electron‐rich unit, either a naphthalene derivative or a hydroquinone ring, and the tetracationic cyclophane are covalently linked. We have demonstrated that the π‐electron‐rich residue in this system is totally “self‐complexed” by the cyclophane to which it is covalently attached. Additionally, the self‐complexation can be switched “off” and “on” by electrochemical two‐electron reductions and oxidations, respectively, of the tetracationic cyclophane component. Thus, we have achieved the construction of two switches at the nanoscale level, one driven by photons and the other by electrons.

  DOI：

  10.1002/chem.19970030123

文献信息

• Thermodynamic forecasting of mechanically interlocked switches
  作者：Mark A. Olson、Adam B. Braunschweig、Taichi Ikeda、Lei Fang、Ali Trabolsi、Alexandra M. Z. Slawin、Saeed I. Khan、J. Fraser Stoddart

  DOI：10.1039/b911874h

  日期：——

  Mechanically interlocked molecular (MIM) switches in the form of bistable [2]rotaxanes and [2]catenanes have proven to be—when incorporated in molecular electronic devices (MEDs) and in nanoelectromechanical systems (NEMS)—a realistic and viable alternative to the silicon chip density challenge. Structural modifications and chemical environment can have a large impact on the relaxation thermodynamics

  机械稳定的分子互锁（MIM）开关以双稳态[2]轮烷和[2]邻苯二酚的形式被证明是-当结合到分子电子设备（MED）和纳米机电系统（NEMS）中时，是一种切实可行的替代方法硅芯片密度挑战。结构修饰和化学环境可能会对分子运动的弛豫热力学产生重大影响，例如负责基于MIM的设备运行的双稳态轮烷和链烷中的平移和环旋。结构修饰对自由能差（ΔG o对于可切换MIM中的平衡过程，可以通过首先考虑其前体假轮烷中存在的相互作用来预测。通过使用等温滴定微量热法（ITC）研究X射线晶体学数据，研究了一系列具有不同供体的单取代受体主环环烷的伪轮烷形成的热力学参数，以及伪轮烷与非共价键相互作用之间的明显联系。可以确定在机械结合形成后仍然存在的MIM。它遵循的变化（ΔΔ ģ ø在自由能不同pseudorotaxanes的形成过程中的差异值）随后可被外推到预测Δ ģ ö使用相同的施主-受主识别组件，与模拟MIM开关中的开关
• Synthesis and characterization of a paramagnetic receptor based on cyclobis(paraquat-p-phenylene) tetracation
  作者：Andrea Margotti、Costanza Casati、Marco Lucarini、Elisabetta Mezzina

  DOI：10.1016/j.tetlet.2008.05.088

  日期：2008.8

  Synthesis of a new class of π-electron-deficient tetracationic cyclophane ring, cyclobis(paraquat-p-phenylene), carrying one or two paramagnetic side-arms based on 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) moiety has been achieved in five steps starting from 2,5-dimethyl benzoic acid. The possibility of exploiting the proposed cyclophanes as hosts in rotaxane-like structures was tested preparing

  合成一种新型的π电子缺陷型四阳离子环烷环，环双（百草枯-对苯撑），该环带有一个或两个基于2,2,6,6-四甲基哌啶-N-氧基（TEMPO）的顺磁侧臂从2，5-二甲基苯甲酸开始，已在五个步骤中实现了部分的化学式。在存在1,5-二甲氧基萘（DMN）的情况下，通过削波程序测试了利用拟议的环烷类作为轮烷样结构中的宿主的可能性，从而制备了自由基受体。模板的添加允许使用DMN隔离单自由基复合物。
• Benniston, Andrew C.; Gardner, Struan; Farrugia, Louis J., Journal of Chemical Research, Miniprint, 2000, # 8, p. 901 - 930
  作者：Benniston, Andrew C.、Gardner, Struan、Farrugia, Louis J.、Harriman, Anthony

  DOI：——

  日期：——
• The synthesis of a pyrrole-functionalized cyclobis(paraquat-p-phenylene) derivative and its corresponding [2]rotaxane and [2]catenane and their subsequent deposition onto an electrode surface
  作者：Graeme Cooke、Lee M. Daniels、Francine Cazier、James F. Garety、Shanika Gunatilaka Hewage、Andrew Parkin、Gouher Rabani、Vincent M. Rotello、Chick C. Wilson、Patrice Woisel

  DOI：10.1016/j.tet.2007.08.027

  日期：2007.11

  We report the convenient synthesis of a pyrrole-functionalized tetracationic cyclophane, [2]rotaxane, and [2]catenane. X-ray crystallography has confirmed the interlocked structure of the catenane. We have investigated the solution properties of these systems using solution electrochemistry, NMR, and UV-vis spectroscopy. We have also demonstrated that it is possible to immobilize these systems onto a platinum working electrode surface. We have shown that films of the cyclophane have the ability to undergo complexation with a di-alkyloxynaphthalene derivative. (c) 2007 Elsevier Ltd. All rights reserved.
• A Tuneable Self-Complexing Molecular Switch
  作者：Graeme Cooke、Patrice Woisel、Marc Bria、François Delattre、James F. Garety、Shanika Gunatilaka Hewage、Gouher Rabani、Georgina M. Rosair

  DOI：10.1021/ol0602553

  日期：2006.3.1

  A new self-complexing donor-acceptor system has been synthesized that has the propensity to undergo intramolecular decomplexation under thermal and electrochemical perturbation and upon addition of a competitive guest for the cyclophane's cavity.