2,5-bis(bromomethyl)benzoyl chloride | 189026-88-8

• 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)benzoyl chloride
• CAS: 189026-88-8
• 化学式: C₉H₇Br₂ClO
• 分子量: 326.415
• InChiKey: KTWHHOUGVDYUGA-UHFFFAOYSA-N

物化性质

• 沸点：
  377.8±42.0 °C(Predicted)
• 密度：
  1.867±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2,5-bis(bromomethyl)benzoyl chloride 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 172.0h， 生成
  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
• 作为产物：
  描述：

  2,5-双(溴甲基)苯甲酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以95%的产率得到2,5-bis(bromomethyl)benzoyl chloride
  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

• Towards mechanically linked polyrotaxanes by sequential deprotection–coupling steps of bifunctional rotaxanes
  作者：Michel P. L. Werts、Maarten van den Boogaard、Georges Hadziioannou、Gerasimos M. Tsivgoulis

  DOI：10.1039/a900914k

  日期：——

  The monomer rotaxane 13, bearing two protected functional groups, is used to obtain a dimer, following a new approach of sequential deprotection–coupling steps which can lead to mechanically linked polyrotaxanes.

  单体旋转烷（rotaxane）13，含有两个保护的功能团，用于获取一个二聚体，采用一种新的顺序去保护-耦合步骤的方法，这可以导致机械连接的聚旋转烷（polyrotaxanes）的形成。
• Mechanically Linked Polyrotaxanes:  A Stepwise Approach
  作者：Michel P. L. Werts、Maarten van den Boogaard、Gerasimos M. Tsivgoulis、Georges Hadziioannou

  DOI：10.1021/ma034521t

  日期：2003.9.1

  A new synthetic approach for the preparation of mechanically linked polyrotaxanes was developed. Two variations of rotaxane monomers were synthesized, based on diphenylmethane and tetraphenylmethane blocking groups. Both rotaxanes bear a protected phenol functionality in the dumbbell-shaped part and a protected carboxylic acid functionality in the cyclic component. Via a "stepwise" polymerization, a rotaxane dimer and a rotaxane tetramer have been obtained. The procedure involves selective deprotection of the two functional groups in separate batches and a subsequent coupling reaction of the produced monofunctional/monoprotected monomers so that a dimer is formed. Longer and monodisperse oligomers can easily be obtained by repetition of this procedure. In addition, deprotection of both functionalities in the dimer and subsequent esterification resulted in the formation of a polymer with a molecular weight of ca. 400 000. The molecules obtained were isolated and characterized by H-1 NMR and mass spectrometry.
• 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：——