8,8'-bis(bromomethyl)-2,2'-binaphthalene | 691004-99-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8,8'-bis(bromomethyl)-2,2'-binaphthalene
• 英文别名: 1-(Bromomethyl)-7-[8-(bromomethyl)naphthalen-2-yl]naphthalene
• CAS: 691004-99-6
• 化学式: C₂₂H₁₆Br₂
• 分子量: 440.177
• InChiKey: KXTTUOLVLSNRDK-UHFFFAOYSA-N

物化性质

• 沸点：
  552.0±45.0 °C(Predicted)
• 密度：
  1.561±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  8,8'-bis(bromomethyl)-2,2'-binaphthalene 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以80%的产率得到8,8'-bis(azidomethyl)-2,2'-binaphthalene
  参考文献：
  名称：

  UV–vis and fluorescence spectroscopic detection of anions by the conformational restriction of 2,2′-binaphthalene derivatives bearing thiourea groups through a methylene spacer

  摘要：

  Novel fluorescence receptors, 2 and 3 based on 2,2'-binaphthalene possessing thiourea moieties via a methylene spacer have been synthesized. Hydrogen bonds of NH groups of thiourea moieties with acetate anion were confirmed by H-1 NMR study in MeCN-d(3). These receptors showed characteristic UV-vis spectral changes through isosbestic points on complexation with anions inspite of lacking conjugation between the chromophore and the binding sites in polar organic solvent such as acetonitfile. The UV-vis spectral changes arise from the conformational restriction of the 2,2'-binaphthyl skeleton on the complexation. The receptors exhibit high selectivities for AcO- and F-. The fluorescence intensity of the receptors decreases with the increasing amount of the AcO-, however, addition of F- induces a different change in its fluorescence spectrum, in which shorter emission of the receptors decreases with the increase in F- concentration, while the longer emission of the receptors increases through an isoemissive point in MeCN. The results suggest that favorable dual-wavelength ratiometric fluorescence measurement can be conducted by the receptors for F-. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.002
• 作为产物：
  描述：

  8,8'-dimethyl-2,2'-binaphthalene 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 以76%的产率得到8,8'-bis(bromomethyl)-2,2'-binaphthalene
  参考文献：
  名称：

  Synthesis of a novel intercalator based on 2,2′-binaphthalene bearing dimethylammonium groups

  摘要：

  A novel type of DNA intercalator, 8,8'-bis(dimethylaminomethyl)-2,2-binaphthalene (1) based on 2,2'-binaphthalene skeleton, was prepared via homocoupling of 7-bromo-1-methylnaphthalene as a key step. The binding ability of 1 for calf thymus (CT) DNA was evaluated by UV-vis and fluorescence spectroscopic titrations and the melting temperature of CT DNA. The apparent association constant of 1 with CT DNA was larger than that of ethidium bromide (EB). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.061

文献信息

• Pyrophosphate selective recognition by a Zn²⁺ complex of a 2,2′-binaphthalene derivative bearing di(2-pyridylmethyl)aminomethyl groups in aqueous solution
  作者：Shin-ichi Kondo、Yasunori Nakadai、Masafumi Unno

  DOI：10.1039/c4ra01941e

  日期：——

  A dinuclear zinc complex of a 2,2′-binaphthalene derivative selectively recognized a pyrophosphate anion.

  一种含有2,2'-联萘衍生物的双核锌配合物能够选择性地识别焦磷酸根离子。
• Recognition of dicarboxylates in aqueous acetonitrile by a dinuclear zinc(II) complex of 2,2’-binaphthalene-based receptor
  作者：Shin-ichi Kondo、Yasunori Nakadai、Masafumi Unno

  DOI：10.1080/10610278.2018.1522445

  日期：2019.1.2

  8ʹ-positions ([Zn2L]4+) by UV-vis and fluorescence spectral titrations in an aqueous solvent was investigated. In a series of α,ω-dicarboxylate, receptor [Zn2L]4+ showed the highest binding affinity for succinate and UV-vis and fluorescence changes were also largest upon the addition of this guest. In a series of phthalate derivatives, phthalate was strongly bound by [Zn2L]4+. The characteristic UV-vis and

  摘要：通过紫外-可见光和荧光光谱滴定，在 8 位和 8 位带有二（2-吡啶基）氨基甲基（[Zn2L]4+）的 2,2ʹ-联萘的双核锌（II）配合物对二羧酸盐的分子识别在水性溶剂中进行了研究。在一系列 α,ω-二羧酸盐中，受体 [Zn2L]4+ 对琥珀酸盐和 UV-vis 的结合亲和力最高，加入该客体后，荧光变化也最大。在一系列邻苯二甲酸酯衍生物中，邻苯二甲酸酯与 [Zn2L]4+ 紧密结合。UV-vis 和荧光的特征变化很大程度上取决于通过光谱滴定和 DFT 计算估计的复合物 [Zn2L]4+· 二羧酸盐的两个萘基的二面角。图形概要
• Anion recognition by 2,2′-binaphthalene bearing imidazolium groups in MeCN
  作者：Shin-ichi Kondo

  DOI：10.1080/10610278.2010.506554

  日期：2011.1.1

  A novel anion receptor 1b based on 2,2'-binaphthalene bearing two imidazolium groups was prepared. UV-vis spectra of 1b showed a marked hypochromic shift at 310nm upon the addition of anions because of the restriction of the rotation around the single bond connecting two naphthyl moieties by cooperative anion binding with two imidazolium moieties. The order of the spectral changes and the association constants was [image omitted]. However, fluorescence changes upon the addition of these anions showed characteristics depending on the anions added. 1H NMR titration revealed that hydrogen bonds were formed by six C-H groups to recognise the anions.
• Barium ion sensing by a 2,2′-binaphthalene derivative bearing two monoaza-15-crown-5 ethers
  作者：Shin-ichi Kondo、Tomoko Kinjo、Yumihiko Yano

  DOI：10.1016/j.tetlet.2005.03.054

  日期：2005.5

  A novel fluoroionophore 1 based on 2,2'-binaphthalene bearing two monoaza-15-crown-5 ethers at 8- and 8'-positions was prepared. UV-vis and fluorescence responses of 1 upon the addition of alkali and alkaline earth metal cations were evaluated in 15% MeOH-MeCN. Receptor 1 showed unique response for Ba2+ due to the formation of an intramolecular sandwich complex. (c) 2005 Elsevier Ltd. All rights reserved.