6-(溴甲基)-2,2'-联吡啶 | 83478-63-1

• 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
• 中文名称: 6-(溴甲基)-2,2'-联吡啶
• 英文名称: 6-bromomethyl-2,2'-bipyridine
• 英文别名: 6-bromomethyl-2,2'-dipyridine；6-(bromomethyl)-2,2’-bipyridine；6-(Bromomethyl)-2,2'-bipyridine；2-(bromomethyl)-6-pyridin-2-ylpyridine
• CAS: 83478-63-1
• 化学式: C₁₁H₉BrN₂
• 分子量: 249.11
• InChiKey: NBLYCBYEQGWSHH-UHFFFAOYSA-N

物化性质

• 熔点：
  65-66 °C
• 沸点：
  339.4±32.0 °C(Predicted)
• 密度：
  1.459±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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-(溴甲基)-2,2'-联吡啶 在 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 生成 6-(hydroxymethyl)-2,2'-bipyridine
  参考文献：
  名称：

  Potts, Kevin T., Bulletin des Societes Chimiques Belges, 1990, vol. 99, # 9, p. 741 - 768

  摘要：

  DOI：
• 作为产物：
  描述：

  [2,2-联吡啶]-6-甲醛 在 sodium tetrahydroborate 、 四溴化碳 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 6-(溴甲基)-2,2'-联吡啶
  参考文献：
  名称：

  Synthesis of ι-(bromomethyl)bipyridines and related ι-(bromomethyl)pyridinoheteroaromatics: useful functional tools for ligands in host molecules

  摘要：

  Pyridines and 2,2'-bipyridines have been employed as useful ligands in molecular recognition chemistries. Halomethyl-substituted bipyridine or oligopyridine derivatives were required for the assembly of bipyridine or oligopyridine units with a supporting mother functional part in artificial biofunctional molecules. A series of omega-(bromomethyl)bipyridines and related omega-(bromomethyl)pyridinoheteroaromatic compounds (types I-III) were synthesized in this paper. Preparation of oligopyridines and pyridinoheteroaromatic compounds have been carried out by either intermolecular ligand coupling of alkyl heteroaryl sulfoxide with pyridyllithium or intramolecular ligand coupling of pyridyl heteroaryl sulfoxide with methylmagnesium bromide for the type I compounds. The type II and III compounds were synthesized by addition of pyridyllithium to pyridinecarboxaldehyde. The omega-bromo group was introduced by radical bromination reaction of methylpyridyl group using NBS and BPO (dibenzoyl peroxide) or bromination of omega-(hydroxymethyl)pyridine using a combination of CBr4 and Ph3P.

  DOI：

  10.1021/jo00068a037

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。
• Amino acid ester salt recognition by ferrocene-based ditopic receptor bearing oligoethylene glycol with pendant bipy subunits: CV, UV-vis and ESR studies
  作者：Takashi Murashima、Sayo Tsukiyama、Satoshi Fujii、Kazuyuki Hayata、Hiroshi Sakai、Toshifumi Miyazawa、Takashi Yamada

  DOI：10.1039/b511233h

  日期：——

  The novel ferrocene-based ditopic receptor 1 was synthesized. This receptor bears two oligoethylene glycol arms with pendant 2,2′-bipyridine unit at the identical cyclopentadienyl rings, CuI cation binds to 1 to form the 1 : 1 complex (1·CuI) with the cavity consisting of polyether, and the resulting complex acts as a receptor for amino acid ester salts to give the ditopic complex (1·CuI·AAOMe–HCl). The 1H NMR spectrum of 1·CuI·LeuOMe–HCl exhibits strong broadening at the bipyridine region, and the ESR spectrum of the same sample gives the signals assigned as CuII species. With these data, the binding of 1·CuI towards AAOMe·HCl leads to the conformational change, and the CuI complex is simultaneously oxidized to the CuII complex.

  新型二萜基钴配合物受体1已被合成。该受体具有两个相同环戊二烯环上悬挂的2,2′-联吡啶单元，以及两个聚乙二醇臂。铜(I)离子与1结合形成1∶1的络合物（1·CuI），其空腔由聚醚构成，所得络合物作为氨基酸酯盐的受体，形成二萜基络合物（1·CuI·AAOMe–HCl）。1·CuI·LeuOMe–HCl的1H NMR谱在联吡啶区域展现出强烈的展宽，而相同样品的ESR谱给出了归属为CuII物种的信号。基于这些数据，1·CuI与AAOMe·HCl结合导致构象变化，同时CuI络合物被氧化为CuII络合物。
• [EN] COMPOUNDS AND METHODS FOR CONJUGATION OF BIOMOLECULES<br/>[FR] COMPOSÉS ET PROCÉDÉS DE CONJUGAISON DE BIOMOLÉCULES
  申请人：LIFE TECHNOLOGIES CORP

  公开号：WO2012121973A1

  公开（公告）日：2012-09-13

  Low-copper click chemistry, 1.3-dipolar cycloadditions, and Staudinger ligations for modifying biomolecules is provided. Compositions, methods, and kits relating to low-copper click chemistry, 1.3-dipolar cycloadditions, and Staudinger ligations are also provided.

  低铜点击化学，1,3-双极环加成和施陀林反应用于修饰生物分子。涉及低铜点击化学，1,3-双极环加成和施陀林反应的组合物、方法和试剂盒也提供。
• Copper-Chelating Azides for Efficient Click Conjugation Reactions in Complex Media
  作者：Valentina Bevilacqua、Mathias King、Manon Chaumontet、Marc Nothisen、Sandra Gabillet、David Buisson、Céline Puente、Alain Wagner、Frédéric Taran

  DOI：10.1002/anie.201310671

  日期：2014.6.2

  chelation‐assisted copper catalysis was employed for the development of new azides that display unprecedented reactivity in the copper(I)‐catalyzed azide–alkyne [3+2] cycloaddition (CuAAC) reaction. Azides that bear strong copper‐chelating moieties were synthesized; these functional groups allow the formation of azide copper complexes that react almost instantaneously with alkynes under diluted conditions. Efficient

  螯合辅助铜催化的概念被用于开发新的叠氮化物，这些新叠氮化物在铜（I）催化的叠氮化物-炔烃[3 + 2]环加成（CuAAC）反应中显示出前所未有的反应活性。合成了具有强铜螯合部分的叠氮化物；这些官能团允许形成叠氮化物铜络合物，在稀释条件下，它们几乎可以瞬间与炔烃反应。在低浓度和仅含一当量铜的复杂介质中即可进行有效的连接，从而提高了CuAAC反应的生物相容性。此外，这种点击反应通过荧光测量允许生物活性化合物在活细胞内定位。
• Self-assembling, patterning and SPR imaging of a 1,3 alternate bis(dipyridyl)calix[4]arene derivative–Cu²⁺complex immobilized on to Au(111) surfaces
  作者：Giuseppe Arena、Annalinda Contino、Elisa Longo、Carmelo Sgarlata、Giuseppe Spoto、Valeria Zito

  DOI：10.1039/b408326c

  日期：——

  The electrochemically switchable Cu(2+) complex of a 1,3 alternate bis(dipyridyl)calix[4]arene derivative forms self-assembled monolayers on Au(111) surfaces. The receptor is patterned on the surface by using microcontact printing procedures and the resulting surface is imaged via SPR.

  1,3交替双（二吡啶基）杯[4]芳烃衍生物的电化学可切换的Cu（2+）络合物在Au（111）表面上形成自组装单层。通过使用微接触印刷程序在表面上对受体进行构图，然后通过SPR对所得表面进行成像。