1,3-dibromo-5-(dodecyloxy)benzene | 476195-69-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,3-dibromo-5-(dodecyloxy)benzene
• 英文别名: 1,3-Dibromo-5-dodecoxybenzene
• CAS: 476195-69-4
• 化学式: C₁₈H₂₈Br₂O
• 分子量: 420.228
• InChiKey: SZNLOADQHNFDQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-dibromo-5-(dodecyloxy)benzene 在 三乙胺 copper(l) iodide 、 正丁基锂 、 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 22.09h， 生成 2-[3,5-Bis[2-[3-dodecoxy-5-(2-trimethylsilylethynyl)phenyl]ethynyl]phenyl]ethoxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  Hydrogen-Bond-Assisted π-Stacking of Shape-Persistent Cyclophanes

  摘要：

  The pi-stacking interaction between shape-persistent cyclophanes works cooperatively with multiple hydrogen bonding sites to form cyclophane dimers. These findings considerably broaden the applicability of pi-stacking interactions as a driving force in self-assembly chemistry. A gel formation effect was also noticed in one of the cyclophanes.

  DOI：

  10.1021/jo025723a
• 作为产物：
  描述：

  五溴苯酚 在 三氯化铝 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 36.0h， 生成 1,3-dibromo-5-(dodecyloxy)benzene
  参考文献：
  名称：

  Hydrogen-Bond-Assisted π-Stacking of Shape-Persistent Cyclophanes

  摘要：

  The pi-stacking interaction between shape-persistent cyclophanes works cooperatively with multiple hydrogen bonding sites to form cyclophane dimers. These findings considerably broaden the applicability of pi-stacking interactions as a driving force in self-assembly chemistry. A gel formation effect was also noticed in one of the cyclophanes.

  DOI：

  10.1021/jo025723a

文献信息

• Oligo(aryl-triazole)s CH⋯Cl⁻interactions guide chloride efficient and selective transmembrane transport
  作者：Sujun Chen、Sitong Zhang、Chunyan Bao、Chenxi Wang、Qiuning Lin、Linyong Zhu

  DOI：10.1039/c6cc07792g

  日期：——

  Using specific C–H⋯Cl⁻interactions, oligo(aryl-triazole) based transporters realized efficient/selective Cl⁻transmembrane transport by adjusting their molecular lipophilicity and anion affinity.

  使用特定的C–H⋯Cl⁻相互作用，基于寡聚(芳基-三唑)的传输体通过调整它们的分子亲脂性和阴离子亲和力，实现了高效/选择性的Cl⁻跨膜传输。
• Radical/Anionic S_RN1-Type Polymerization for Preparation of Oligoarenes
  作者：Sandip Murarka、Armido Studer

  DOI：10.1002/anie.201206096

  日期：2012.12.3

  Radicals and anions: The TEMPO‐mediated oxidation of magnesiated iodoarenes A provides highly regioregular poly(m‐phenylenes) by strictly alternating anionic/radical cross‐over chain‐growth polymerization. Poly(m‐phenylenes) with mean molecular weight (Mn) of up to 20 000 g mol−1 can be prepared under mild conditions by this method. The approach is a new concept for transition‐metal‐free polyarene

  自由基和阴离子：镁化iodoarenes的TEMPO介导的氧化甲提供高度立体规则性聚（米-phenylenes）通过严格交替的阴离子/自由基交叉链增长聚合。聚（米-phenylenes），平均分子量（中号Ñ高达20的）000克摩尔-1可以在温和的条件下通过该方法来制备。该方法是用于无过渡金属的聚芳烃合成的新概念。TEMPO = 2,2,6,6-四甲基哌啶-N-氧基。
• Palladium-catalyzed borylation of m-dibromobenzene derivative and its applications in one-pot tandem Suzuki–Miyaura arenes synthesis
  作者：Dahai Xie、Rong Li、Dengqing Zhang、Jiena Hu、Duoduo Xiao、Xianying Li、Yunjie Xiang、Wusong Jin

  DOI：10.1016/j.tet.2015.10.011

  日期：2015.11

  One-step synthesis of several α,ω pinacol boronates starting from m-dibromobenzene derivative and bis(pinacolato)diboron through Miyaura reaction has been reported. The present approach provided low to moderate yields of monomer boronates, and trace to low yields of dimmer, trimer and tetramer boronates. Furthermore, the resulted boronates can be followed by Suzuki–Miyaura cross-coupling without purification

  从开始几个α，ω频哪醇硼酸酯一步法合成米已经报道通过宫浦反应二溴苯衍生物和双（频哪醇合）二硼。本方法提供低到中等的单体硼酸酯的产率，和跟踪到的调光器，三聚物和四硼酸酯的产率低。此外，所得到的硼酸酯可以跟随铃木-宫浦不经纯化，这提高了该方法的实用性交叉耦合。
• Enantioselective Pervaporation through Membranes from Poly(1,3-phenyleneethynylene)-based One-handed Helical Foldamer and Unfoldamer
  作者：Makoto Inoue、Masahiro Teraguchi、Toshiki Aoki、Takeshi Namikoshi、Edy Marwanta、Takashi Kaneko

  DOI：10.1246/cl.2011.384

  日期：2011.4.5

  We synthesized two kinds of poly(1,3-phenyleneethynylenes), one has (+)-menthoxycarbonyl groups at all repeating units and the other has (+)-menthoxycarbonyl groups and n-dodecyloxy groups alternately. Self-supporting membranes could be obtained easily by solvent casting. Enantioselective permeations of the polymers were investigated by pervaporation of 2-butanol. Enantioselective permeabilities of the membrane consisting of one-handed helical foldamer and unfoldamer were clarified.

  我们合成了两种聚(1,3-苯乙炔)，一种在所有重复单元上都有(+)-门冬羰基，另一种交替有(+)-门冬羰基和正十二烷氧基。自支撑膜可通过溶剂浇铸法轻松获得。通过对 2-丁醇的渗透研究了聚合物的对映选择渗透性。澄清了由单手螺旋折叠聚合体和展开聚合体组成的膜的对映体选择渗透性。
• Topologically engineering of π-conjugated macrocycles: Tunable emission and photochemical reaction toward multi-cyclic polymers
  作者：Yi Liu、Peng Lei、Yang Feng、Shiwei Fu、Xiaoqing Liu、Siqi Zhang、Bin Tu、Chen Chen、Yifan Li、Lei Wang、Qing-Dao Zeng

  DOI：10.1016/j.cclet.2024.109571

  日期：2024.2

  could yield the dimer triplet excimer on the HOPG surface confirmed by STM investigation. By contrast, highly constrained bicyclic analogue (named as ) with central tetraphenylethene core, displayed high emission quantum yields of 68% both in solution and in the solid state, and was relatively inert to photochemical reactions and yield -dimer on the surface singlet excimer involved [2 + 2] photo-dimerization

  共轭大环的拓扑结构对其光物理和光化学性质有显着影响。在此，通过分子内 McMurry 偶联合成了一系列具有不同拓扑结构的 β-共轭大环化合物。它们的化学结构和大环拓扑结构均已通过 NMR、MALDI-TOF 质谱、晶体分析和扫描隧道显微镜 (STM) 明确证实。根据结构拓扑和结构刚性，这些环状化合物在溶液和固态中表现出明显独特的发射行为和光化学反应。单环亚苯基亚乙烯基大环（表示为 ）表现出聚集诱导的发射行为，更容易在溶液中发生光环化，并且三线态敏化剂由于较低的应变和更丰富的分子内运动而促进光二聚化。经过紫外光照射后，通过STM研究证实，HOPG表面上可以产生相对更柔韧的二聚体三重态准分子。相比之下，具有中心四苯乙烯核心的高度约束的双环类似物（命名为 ）在溶液和固态下均显示出 68% 的高发射量子产率，并且对光化学反应相对惰性，并且涉及表面单线态准分子上的产率二聚体[2+2]光二聚化。基于溶