2,3,6,7-四(溴甲基)萘 | 88903-14-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2,3,6,7-四(溴甲基)萘
• 英文名称: 2,3,6,7-tetrakis(bromomethyl)naphthalene
• 英文别名: 2,3,6,7-tetra(bromomethyl)-naphthalene
• CAS: 88903-14-4
• 化学式: C₁₄H₁₂Br₄
• 分子量: 499.865
• InChiKey: PUMPSEORLQUFCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,3,6,7-四(溴甲基)萘 在 氢氧化钾 、 亚磷酸三乙酯 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 生成 triple-layered <2.2><2.2>naphthalenophane
  参考文献：
  名称：

  三层[2.2][2.2]萘酚的合成、结构和性质

  摘要：

  标题化合物的合成方式与简单获得三层 [2.2][2.2] 对环芳烷类似。通过X射线晶体学分析阐明了其结构。外萘环弯曲成船形，内萘环弯曲成扭曲形式。这些萘在范德华接触内分层堆叠。因此，它们之间存在强烈的跨环π-电子相互作用，从而导致特征红移、增色和电子光谱增宽。这些效果比双层同系物的效果更突出。

  DOI：

  10.1246/bcsj.62.164
• 作为产物：
  描述：

  2,3,6,7-四甲基萘 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 0.5h， 以69%的产率得到2,3,6,7-四(溴甲基)萘
  参考文献：
  名称：

  三层[2.2][2.2]萘酚的合成、结构和性质

  摘要：

  标题化合物的合成方式与简单获得三层 [2.2][2.2] 对环芳烷类似。通过X射线晶体学分析阐明了其结构。外萘环弯曲成船形，内萘环弯曲成扭曲形式。这些萘在范德华接触内分层堆叠。因此，它们之间存在强烈的跨环π-电子相互作用，从而导致特征红移、增色和电子光谱增宽。这些效果比双层同系物的效果更突出。

  DOI：

  10.1246/bcsj.62.164

文献信息

• Chiral Softballs:  Synthesis and Molecular Recognition Properties
  作者：José M. Rivera、Tomás Martín、Julius Rebek

  DOI：10.1021/ja004080i

  日期：2001.6.1

  dimeric softball chiral although the monomer itself is achiral. The dimers represent capsules with dissymmetric cavities with volumes ranging from 190 to 390 A(3). The cavities are distorted spheres, and asymmetric guests, such as naturally occurring terpenes, generally prefer one enantiomer of the capsule to its mirror image. The selectivities are moderate (up to 4:1). The complexation studies show that

  对垒球的不同同源物进行了研究，以探索对映选择性封装的结构变体。尽管单体本身是非手性的，但单体亚基中的两个不同的间隔元件使二聚垒球具有手性。二聚体代表具有不对称腔的胶囊，体积范围为 190 到 390 A(3)。空腔是扭曲的球体，不对称的客体，如天然存在的萜烯，通常更喜欢胶囊的一种对映异构体而不是它的镜像。选择性适中（高达 4:1）。络合研究表明，宿主胶囊足够灵活，可以在客体周围舒适地安排自己，但仍保持足够的刚度，以受到手性客体占用的影响。
• An Attempted Synthesis of [7][7]Circulene: Synthesis and Characterization of Triple-Layered [2.2]Phenanthreno[2.2]naphthalenophenanthrenophane
  作者：Koji Yano、Susumu Matsuda、Keita Tani、Koji Yamamoto、Hiroshi Matsubara

  DOI：10.1246/bcsj.72.2111

  日期：1999.9

  The synthesis of the title compound, a triple-layered cyclophane, is described. The unusually strained structure was supported by its 1H NMR spectra, electronic spectra, and X-ray crystallographic analysis.

  描述了标题化合物（三层环烷）的合成。其 1H NMR 光谱、电子光谱和 X 射线晶体学分析支持了异常应变的结构。
• Redox responsive molecular tweezers with tetrathiafulvalene units: synthesis, electrochemistry, and binding properties
  作者：Maciej Skibiński、Rafael Gómez、Enno Lork、Vladimir A. Azov

  DOI：10.1016/j.tet.2009.10.052

  日期：2009.12

  Several new molecular tweezers with tetrathiafulvalene (TTF) arms as well as mono-TTF derivatives bearing 3,5-di-tert-butylbenzylthio groups to provide enhanced solubility were prepared starting from a bis-cyanoethyl-protected tetrathiafulvalene derivative. The X-ray crystallographic analysis of 3 and 7a showed highly distorted TTF groups and absence of close TTF-TTF contacts in the crystalline state. Comparative cyclic voltammetry (CV) measurements demonstrated that through space distance-dependent TTF-TTF interactions take place in the TTF-containing molecular tweezers, leading to electronic pairing with formation of mixed valence [TTF](2)(+center dot) species and splitting of the first oxidation wave. TTF-containing molecular tweezers were successfully tested as receptors for several electron-deficient substances. (C) 2009 Elsevier Ltd. All rights reserved.
• Triple-layered [2.2]naphthalenophane
  作者：Tetsuo Otsubo、Fumio Ogura、Soichi Misumi

  DOI：10.1016/s0040-4039(00)94024-3

  日期：1983.1
• Synthesis and Self-Assembly of Pseudo-Spherical Homo- and Heterodimeric Capsules
  作者：Carlos Valdes、Urs P. Spitz、Leticia M. Toledo、Stefan W. Kubik、Julius Rebek

  DOI：10.1021/ja00156a010

  日期：1995.12

  Experimental details are given for the synthesis and characterization of several new molecules capable of self-assembly. The new molecules feature glycoluril subunits held apart by various rigid spacers, ethylene (2), naphthalene (3), and ethenoanthracene (4), and assemble through hydrogen bonds into pseudo-spherical dimeric capsules. The nature of their assembly is demonstrated by the X-ray crystal structure of capsules 1.1. The capsules are shown to enclose smaller guest molecules in a reversible manner. Direct evidence of the guest molecules inside the capsules from NMR is presented. In addition to self-assembling dimerically, these new molecules are shown to disproportionate into hybrid species or heterodimers. The resulting new capsules feature internal cavities of varying sizes and shapes. Formation of hybrid dimers 1.2, 1.4, and 3.4 is observed in solutions containing mixtures of two homodimers. The dispropoaionation equilibria could be manipulated by the addition of appropriately sized solvents as guests. Even the energetically unlikely hybrids 1.4 and 3.4 are found to be the dominant species when suitable guests such as CDBr3 are present. Evidence of the existence of the heterodimers is presented from NOE measurements. Factors controlling the heterodimerization are discussed.