dimethyl 2,5-bis(bromomethyl)terephthalate | 54100-54-8

• 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: dimethyl 2,5-bis(bromomethyl)terephthalate
• 英文别名: 1,4-Dimethyl 2,5-bis(bromomethyl)-1,4-benzenedicarboxylate；dimethyl 2,5-bis(bromomethyl)benzene-1,4-dicarboxylate
• CAS: 54100-54-8
• 化学式: C₁₂H₁₂Br₂O₄
• 分子量: 380.033
• InChiKey: UJIJTCNXMDVIQV-UHFFFAOYSA-N

物化性质

• 熔点：
  110-112 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  457.9±45.0 °C(Predicted)
• 密度：
  1.695±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2917399090

反应信息

• 作为反应物：
  描述：

  dimethyl 2,5-bis(bromomethyl)terephthalate 在 lithium aluminium tetrahydride 、 三溴化磷 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 二甲基亚砜 、 甲苯 为溶剂， 反应 40.5h， 生成 5,8-Dimethoxy<3>(2,5)tetracyanchinodimethano<3>paracyclophan
  参考文献：
  名称：

  Staab, Heinz A.; Knaus, Guenter H.; Henke, Hans-Eckard, Chemische Berichte, 1983, vol. 116, # 8, p. 2785 - 2807

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5-二甲基对苯二腈 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 甲烷磺酸 作用下， 以 四氯化碳 、 二乙二醇 为溶剂， 反应 34.0h， 生成 dimethyl 2,5-bis(bromomethyl)terephthalate
  参考文献：
  名称：

  A Selective Receptor for Arginine Derivatives in Aqueous Media. Energetic Consequences of Salt Bridges That Are Highly Exposed to Water

  摘要：

  Quantitative measures of salt-bridge-type interactions in a highly exposed aqueous environment have been obtained by modifying the well-studied cyclophane platform 1 to include carboxylates in close proximity to bound, cationic guests, producing hosts 2 and 3. Many guests show significantly enhanced binding to 2 and 3, but cations of the RNMe3+ type show little or no enhancement. We propose that the latter observations result from the fact that RNMe3+ compounds have very diffuse positive charges. Guests that show enhanced binding have focused regions of large, positive electrostatic potential. The highly charged 3 is able to bind very polar, very well-solvated guests, including a series of arginine-based dipeptides. Neutral, water-soluble host 4 was prepared and found to show a decreased affinity for cationic guests. We propose a novel induced dipole mechanism to rationalize these results.

  DOI：

  10.1021/ja982499r

文献信息

• Janus-Like 3D Tectons: Self-Assembled 2D Arrays of Functional Units at a Defined Distance from the Substrate
  作者：David Bléger、Fabrice Mathevet、David Kreher、André-Jean Attias、Amandine Bocheux、Sylvain Latil、Ludovic Douillard、Céline Fiorini-Debuisschert、Fabrice Charra

  DOI：10.1002/anie.201008212

  日期：2011.7.11

  Janus‐like 3D tecton is a doubly functionalized molecular building block that consists of two different faces (see picture, gray: A and blue: B) linked by a rigid spacer. A is designed to act as a pedestal capable of guiding 2D self‐assembly on the substrate, while B is a functional entity. This versatile approach allows for the creation of periodic arrays of functional units at a defined distance from the

  Janus面：类似于Janus的3D构造是一种双重功能化的分子构造块，它由两个不同的面（参见图片，灰色：A和蓝色：B）组成，并通过刚性垫片连接。A被设计为能够在基板上引导2D自组装的基座，而B是一个功能实体。这种通用的方法允许在距导电基板一定距离处创建功能单元的周期性阵列。
• [EN] METHODS FOR IDENTIFYING PROTEINS BY USING SYNTHETIC RECEPTORS<br/>[FR] PROCÉDÉS D'IDENTIFICATION DE PROTÉINES À L'AIDE DE RÉCEPTEURS SYNTHÉTIQUES
  申请人：UCB BIOPHARMA SPRL

  公开号：WO2017211985A1

  公开（公告）日：2017-12-14

  The invention relates to oligomeric macrocycles and to uses thereof as receptors for recognition of protein post-translational modifications (PTM) or specific motifs in proteins.

  这项发明涉及寡聚巨环及其用作识别蛋白质翻译后修饰（PTM）或蛋白质中特定基序的受体的用途。
• Paracyclophanes: Extending the Bridges. Synthesis
  作者：Zissis Pechlivanidis、Henning Hopf、Ludger Ernst

  DOI：10.1002/ejoc.200800494

  日期：2009.1

  [3.2]paracyclophane (10), [4.2]paracyclophane (14), [4.3]paracyclophane (19) as well as several derivatives of these compounds – among others the bromides 25, the ester 31, the diesters 40–43 – are described using well-established methods of cyclophane chemistry (ring-closure reactions leading to thiacyclophanes, ring contraction by sulfone pyrolysis). The parent systems and their derivatives are now

  制备 [3.2] 对环烷 (10)、[4.2] 对环烷 (14)、[4.3] 对环烷 (19) 以及这些化合物的几种衍生物——其中包括溴化物 25、酯 31、二酯 40——的令人满意的路线43 – 使用成熟的环芳化学方法（导致硫环芳烃的闭环反应，砜热解引起的环收缩）进行描述。母体系统及其衍生物现在可提供克级数量，可用于研究它们的化学性质。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009）
• Optical Resolution, Absolute Configuration, and Chiroptical Properties of Three-Layered [3.3]Paracyclophane
  作者：Atsuya Muranaka、Masahiko Shibahara、Motonori Watanabe、Taisuke Matsumoto、Teruo Shinmyozu、Nagao Kobayashi

  DOI：10.1021/jo801441h

  日期：2008.11.21

  3]PCP), 1, has been resolved into two enantiomers, and their absolute configuration was determined from a comparison of experimental chiroptical properties and density functional theory (DFT) calculations. A simple model comprising two p-xylenes and 1,2,4,5-tetramethylbenzene (durene) was used to explain the origin of the chiroptical properties of the three-layered cyclophane system.

  三层[3.3]对环环烷（[3.3] PCP）1的外消旋混合物已拆分为两个对映异构体，并且通过对比实验手性和密度泛函理论（DFT）计算确定了它们的绝对构型。一个简单的模型包含两个对二甲苯和1,2,4,5-四甲基苯（二甲苯）被用来解释三层环烷体系的手性的起源。
• Tuning Supramolecular Polymer Assembly through Stereoelectronic Interactions
  作者：Will R. Henderson、Guancen Liu、Khalil A. Abboud、Ronald K. Castellano

  DOI：10.1021/jacs.1c05522

  日期：2021.8.18

  11-dithia[3.3]paracyclophanes through self-complementary intermolecular and transannular amide hydrogen bonding is presented. An n → π* interaction between the amide hydrogen bonding units and the central bridging atom results from the single-point exchange of a carbon atom for a sulfur atom. This orbital donor–acceptor interaction can be strengthened by oxidizing the sulfide to a sulfone which acts to

  介绍了2,11-二硫杂[3.3]对环烷通过自互补分子间和跨环酰胺氢键的超分子聚合。酰胺氢键单元和中心桥原子之间的 n → π* 相互作用是由碳原子与硫原子的单点交换产生的。这种轨道供体-受体相互作用可以通过将硫化物氧化成砜来加强，该砜起到缩短供体···受体距离和增加轨道重叠的作用。增加的n → π*的实验特征相互作用包括溶液中较大的等速聚合伸长常数、特征键拉伸频率的变化以及通过 X 射线晶体学评估的几何/结构变化。实验数据得到了对组装和非组装 2,11-二硫杂[3.3] 对环芳烃的广泛计算研究以及合理设计的模型系统的支持，以确认立体电子效应对超分子聚合物组装的作用。