6-(Bromomethyl)-2,2':6':2''-terpyridine | 130897-06-2

• 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)-2,2':6':2''-terpyridine
• 英文别名: 6-(bromomethyl)-2,2’:6’,2’’-terpyridine；2-(Bromomethyl)-6-(6-pyridin-2-ylpyridin-2-yl)pyridine
• CAS: 130897-06-2
• 化学式: C₁₆H₁₂BrN₃
• 分子量: 326.195
• InChiKey: DORGBUZFNXRIDP-UHFFFAOYSA-N

物化性质

• 沸点：
  447.2±40.0 °C(Predicted)
• 密度：
  1.423±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(Bromomethyl)-2,2':6':2''-terpyridine 、 二氮杂18-冠醚-6 在 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 以74%的产率得到N,N'-Bis((2,2':6',2''-terpyridin-6-yl)methyl)diaza-18-crown-6
  参考文献：
  名称：

  Side arm effects on cation binding, extraction, and transport functions of oligopyridine-functionalized aza-crown ethers

  摘要：

  A new series of lariat ethers and double-armed crown ethers was prepared in which oligopyridine-functionalized side arms were attached as secondary donor sites. A novel preparative method of oligopyridine derivatives was successfully applied to the synthesis of these crown ethers. Introduction of an oligopyridine-functionalized side arm into the crown ether system, if of the proper chain length and geometrical arrangement, significantly offered three-dimensional complexation with various metal cations suitable for extraction and transport. Liquid-liquid extraction, C-13-NMR binding, and liquid membrane transport experiments revealed that the present type of double-armed crown ethers exhibited cation-binding abilities superior to corresponding lariat ethers.

  DOI：

  10.1021/jo00068a038
• 作为产物：
  描述：

  6-溴-2,2':6',2''-三联吡啶 在 sodium tetrahydroborate 、 正丁基锂 、 四溴化碳 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 6-(Bromomethyl)-2,2':6':2''-terpyridine
  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

• Ipso substitution of 2-alkylsulfinylpyridine by 2-pyridyllithium; a new preparation of oligopyridine and their bromomethyl derivatives
  作者：Junichi Uenishi、Takakazu Tanaka、Shoji Wakabayashi、Shigeru Oae、Hiroshi Tsukube

  DOI：10.1016/s0040-4039(00)97692-5

  日期：1990.1

  Unsymmetrical and symmetrical 2,2′-bipyridines 5 and 6 have been prepared. The methods applied are new and offer efficient syntheses of higher oligopyridines and their bromomethyl derivatives.

  已经制备了不对称和对称的2,2'-联吡啶5和6。所应用的方法是新方法，可提供高级寡吡啶及其溴代甲基衍生物的有效合成方法。
• Bispidine Chelators for Radiopharmaceutical Applications with Lanthanide, Actinide, and Main Group Metal Ions
  作者：Ina Kopp、Patrick Cieslik、Karl Anger、Thomas Josephy、Lucca Neupert、Gunasekaran Velmurugan、Michael Gast、Hubert Wadepohl、Santiago Andrés Brühlmann、Martin Walther、Klaus Kopka、Michael Bachmann、Holger Stephan、Manja Kubeil、Peter Comba

  DOI：10.1021/acs.inorgchem.3c02340

  日期：2023.12.18

  of further optimized bispidine chelators. Second, the coordination chemistry of L2 has been extended to Bi3+, La3+, and Pb2+, including solid state and solution structural work, complex stabilities, radiolabeling, and radiostability studies. All complexes of this ligand (La3+, Ac3+, Lu3+, Bi3+, In3+, and Pb2+), including nuclides for targeted α therapy (TAT), single-photon emission computed tomography

  已知具有双吡啶支架（3,7-二氮杂双环[3.3.1]壬烷）的八齿配体和特别是九齿配体可以有效地与放射性药物化学中感兴趣的一系列金属离子配位，并产生极其稳定和惰性的复合物。九齿双吡啶L 2 （N3 附加三齿联吡啶醋酸盐，N7 附加吡啶甲酸盐）之前已被证明是111 In 3+ 、 177 Lu 3+和225 Ac 3+诊断感兴趣核素的理想螯合剂和治疗，一项针对 SSTR2 特异性奥曲酯的原理验证研究显示了治疗诊断应用的潜力。我们现在已将这些研究扩展到两个方向。首先，我们提出了配体衍生物L 3 ，其中乙酸联吡啶被三联吡啶取代，三联吡啶是金属离子的较软供体，具有更多共价性。 L 3没有实现希望，因为络合作用的效率要低得多。虽然对于 Bi 3+和 Pb 2+来说，配体是一种优异的螯合剂，其性质与L 2相似，但与L 2和225 Ac 3相比，Lu 3+和 La 3+与L 3 的络合作用非常缓慢且效率低下。即使在升高的温度下，
• Potts, Kevin T., Bulletin des Societes Chimiques Belges, 1990, vol. 99, # 9, p. 741 - 768
  作者：Potts, Kevin T.

  DOI：——

  日期：——
• UENISHI, JUNICHI;TANAKA, TAKAKAZU;WAKABAYASHI, SHOJI, TETRAHEDRON LETT., 31,(1990) N2, C. 4625-4628
  作者：UENISHI, JUNICHI、TANAKA, TAKAKAZU、WAKABAYASHI, SHOJI

  DOI：——

  日期：——
• Synthesis of ι-(bromomethyl)bipyridines and related ι-(bromomethyl)pyridinoheteroaromatics: useful functional tools for ligands in host molecules
  作者：Junichi Uenishi、Takakazu Tanaka、Kenji Nishiwaki、Shoji Wakabayashi、Shigeru Oae、Hiroshi Tsukube

  DOI：10.1021/jo00068a037

  日期：1993.7

  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.