6-(bromomethyl)-6'-methyl-2,2'-bipyridine | 96517-98-5

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-(bromomethyl)-6'-methyl-2,2'-bipyridine
• 英文别名: 6-methyl-6'-(bromomethyl)-2,2'-bipyridine；6-(bromomethyl)-6’-methyl-2,2’-bipyridine；2,2'-Bipyridine, 6-(bromomethyl)-6'-methyl-；2-(bromomethyl)-6-(6-methylpyridin-2-yl)pyridine
• CAS: 96517-98-5
• 化学式: C₁₂H₁₁BrN₂
• 分子量: 263.137
• InChiKey: FDZLIXVMGJIMQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(bromomethyl)-6'-methyl-2,2'-bipyridine 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以47%的产率得到6-azidomethyl-6′-methyl-2,2′-bipyridine
  参考文献：
  名称：

  Tris-ACE-(6,6′-bipyridyl)-α-cyclodextrin: synthesis and chirality of the tripodal metal complexes

  摘要：

  This Letter describes the synthesis of a C-3-symmetrical tris-(ACE)-(6,6'-bipyridyl)-alpha-CyD via 'one-pot' Staudinger-Aza-Wittig reaction (SAW). Metal complexation behavior was investigated by UV-vis and Circular Dichroism. Coordination of 6,6'-bipyridyl units with Cu-II and Ni-II cations, spontaneously generates a strong exciton coupling-type positive Cotton effect proving the formation of a Lambda-helix with a left-handed screw propeller (M). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.038
• 作为产物：
  描述：

  6,6'-二甲基-2,2'-联吡啶 在 偶氮二异丁腈 、 1,3,4,6-Tetrabromo-3α,6α-diphenylglycoluril 作用下， 以 四氯化碳 为溶剂， 以71%的产率得到6-(bromomethyl)-6'-methyl-2,2'-bipyridine
  参考文献：
  名称：

  Tris-ACE-α-cyclodextrin tripods: chemistry and metal coordination behaviour

  摘要：

  本研究介绍了通过 "一锅 "施陶丁格-阿扎-维蒂希（SAW）反应合成 C3-对称三-ACE-(6,6â²-双杂环酰)-δ-环糊精的过程。分析了其金属配位化合物的光谱特性。金属超分子螺旋体的自发形成产生了强激子耦合特征，这为了解配合物的性质、几何形状及其绝对构型提供了许多信息。

  DOI：

  10.1039/c3dt51811f

文献信息

• Synthesis and Metal-Binding Properties of Polybipyridine Ligands Derived from Acyclic and Macrocyclic Polyamines
  作者：Raymond Ziessel、Jean-Marie Lehn

  DOI：10.1002/hlca.19900730502

  日期：1990.8.8

  been developed for the preparation of ligands bearing two to six pendent, unsubstituted or substituted 2, 2′-bipyridine groups attached to acyclic (tripode, tetrapode) and macrocyclic (triazanonade-cane, cyclam, hexacyclen, bis(bipyrido)hexaazamacrocycle) polyamines. Ligands 1-5 have been obtained in high yield by condensation of 6-(bromomethyl)-2, 2′-bipyridine (9b) with the corresponding amines in

  已经开发出用于制备配体的合成程序，所述配体带有两个至六个悬垂，未取代或取代的2、2'-联吡啶基团，这些基团连接于无环（三叠，四足）和大环（三嗪酮-甘蔗，Cyclam，六环，双（双吡啶）六氮杂大环） ）多胺。通过在NaOH，H 2 O和MeOH的存在下使6-（溴甲基）-2、2'-联吡啶（9b）与相应的胺缩合，以高收率获得了配体1-5。通过在Na 2存在下分别缩合9b或二或四取代的单（溴甲基）联吡啶10b或11b与相应的胺，可以高收率制备配体6-8。CO 3和MeCN。配体1与Ru II，Fe I，Cr II和Cr III阳离子形成半笼式络合物，与[RuCl 2（bpy）2 ]和[ReCl（CO）5 ]形成三核络合物。四足动物2和六足动物4通过与Fe11盐反应分别得到四核和双核复合物。这些络合物具有各种有趣的物理和化学性质。
• Cation Molecular Exchanger Based on a Conformational Hinge
  作者：Anil Ravi、P. Sivarama Krishnarao、Tatiana A. Shumilova、Victor N. Khrustalev、Tobias Rüffer、Heinrich Lang、Evgeny A. Kataev

  DOI：10.1021/acs.orglett.8b02687

  日期：2018.10.5

  A cation molecular exchanger has been developed that consists of the bipyridine and crown ether receptor subunits. It has been shown that binding of the zinc(II) cation to the bipyridine subunit induces the conformational switching of the crown ether subunits, which results in a release of the potassium cation. Two conformational states of the cation exchanger have been supported by the results from

  已经开发了由联吡啶和冠醚受体亚基组成的阳离子分子交换剂。已经显示锌（II）阳离子与联吡啶亚基的结合诱导冠醚亚基的构象转换，这导致钾阳离子的释放。溶液和固态研究的结果支持了阳离子交换剂的两种构象状态。已经证明，阳离子交换剂能够与由化学刺激诱导的阳离子传感器通信。
• An Attempt to Programme the Orientation of Bis(heterocyclic) Azine Heterotopic Sequences around Ag ^I , Cu ^I and Zn ^II Metal Centres
  作者：Julien Mathieu、Noureddine Ghermani、Nouzha Bouhmaida、Bernard Fenet、Alain Marsura

  DOI：10.1002/ejic.200300958

  日期：2004.8

  Four novel bis(heterocyclic) sequences, which incorporate a 2,2′-bipyridine system with the 2,2′-bithiazole, 4,4′-bithiazole, 2,2′-bipyrazine or 4,4′-bipyrimidine units, have been synthesized. In the presence of stoichiometric amounts of CuI, AgI or ZnII cations, fully oriented discrete head-to-head (H-H) or head-to-tail (H-T) species have been observed by NMR and X-ray crystallography. The orientation

  四个新的双（杂环）序列，将 2,2'-联吡啶系统与 2,2'-联噻唑、4,4'-联噻唑、2,2'-联吡嗪或 4,4'-联嘧啶单元结合在一起，具有被合成。在化学计量的 CuI、AgI 或 ZnII 阳离子存在下，通过 NMR 和 X 射线晶体学观察到完全定向的离散头对头 (HH) 或头对尾 (HT) 物种。在自组装过程中，AgI、CuI 或 Zn II 双核配合物中配体的取向似乎受与不同双（杂环）序列的电子构型相关的电子因素的控制。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Improved Halogenation of Methyl Aromatics and Methyl Heteroaromatics: Unexpected Reactivity of Tetrahalogeno-diphenylglycolurils
  作者：Florian Moretti、Guillaume Poisson、Alain Marsura

  DOI：10.1002/hc.21314

  日期：2016.5

  exploited in a new direction as reagents for free radical substitution toward some N-halosuccinimide nonreactive bis-heterocycles. An unexpected selectivity and reactivity were observed with methyl benzenes, methyl heterocycles, and methyl-bis-heterocycles of interest. A chemometric study has been performed to optimize five independent factors of the chlorination reaction with TCDGU. The predictive model

  1,3,4,6-四氯 (TCDGU) 和 1,3,4,6-四溴-3α,6α-二苯基甘脲平滑卤素氧化剂已被开发用作自由基取代某些 N-卤代琥珀酰亚胺非反应性试剂的新方向双杂环。对于感兴趣的甲基苯、甲基杂环和甲基双杂环，观察到了意想不到的选择性和反应性。已进行化学计量学研究以优化与 TCDGU 氯化反应的五个独立因素。建立了卤化转化率和一氯化比的预测模型。
• A new water-soluble calix[4]arene podand incorporating p-phosphonate groups and 2,2′-bipyridine units
  作者：Nicolas Psychogios、Jean-Bernard Regnouf-de-Vains

  DOI：10.1016/s0040-4039(02)01843-9

  日期：2002.10

  A new water-soluble calix[4]arene-based bipyridyl podand was prepared by incorporation at the upper rim of four phosphonate groups; the association of its hydrophilic and chelating properties was positively evaluated in the complexation of copper(I) in water.

  通过在四个膦酸酯基团的上边缘结合，制备了一种新的基于水溶性杯[4]芳烃的联吡啶荚果。在水中铜（I）的络合过程中，对其亲水性和螯合性能的关联得到了积极的评估。