5-bromomethyl-2,2':6',2''-terpyridine | 172909-19-2

• 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: 5-bromomethyl-2,2':6',2''-terpyridine
• 英文别名: 2-[5-(bromomethyl)pyridin-2-yl]-6-pyridin-2-ylpyridine
• CAS: 172909-19-2
• 化学式: C₁₆H₁₂BrN₃
• 分子量: 326.195
• InChiKey: YGGVXHZHZAKWDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.67
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5,5''-bis(hydroxymethyl)-2,2':6',2''-terpyridine 、 5-bromomethyl-2,2':6',2''-terpyridine 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以74%的产率得到2,6-Bis[5-[[6-(6-pyridin-2-ylpyridin-2-yl)pyridin-3-yl]methoxymethyl]pyridin-2-yl]pyridine
  参考文献：
  名称：

  分子中的信息：异金属双螺旋结构的动态系统中的配体/阳离子编码和自我识别。

  摘要：

  已知双螺旋结构具有自我识别特性，该特征是由所涉及的金属的配位几何形状以及配体的局部性决定的。在三位链中结合三齿（三联吡啶，T）或二齿（联吡啶，B）亚基，可以提供一组能够成对组装以形成双螺旋，同或异链，同或异位的配体，具体取决于涉及的金属。四个配体链BBB，TTT，BBT和TBT与金属离子Cu（I），Cu（II）和Zn（II）构成了双螺旋结构的动态组。这些螺旋分别对应于四，五和六配位的Cu（I），Cu（II）和Zn（II）阳离子的BB，BT和TT对正确编码。

  DOI：

  10.1002/chem.200600143
• 作为产物：
  描述：

  5-methyl-2,2':6',2''-terpyridine 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 1.0h， 以54%的产率得到5-bromomethyl-2,2':6',2''-terpyridine
  参考文献：
  名称：

  Synthesis of two covalently linked bis(2,2′:6′,2″-terpyridine) (terpy) chelating ligands with different length spacers, comparison of the crystal structures of their mononuclear nickel(II) complexes, and kinetic and mechanistic studies of the reaction of one ligand with [Fe(terpy)2]2+

  摘要：

  两种新型共价连接的双(2,2′-¶6′,2′′-吡啶)-螯合六齿配体，1,3-二(2,2′-¶6′,2′′-吡啶-5-基甲基硫醇)丙烷（L1）和1,4-二(2,2′-¶6′,2′′-吡啶-5-基甲基硫醇)丁烷（L2），以及它们的六配位单核金属复合物[ML][PF6]2（M = Fe 和 Ni; L = L1 和 L2）已被合成和表征。通过比较[NiL](PF6)2（L = L1 和 L2）的X射线结构，确认L2具有最佳的连接长度，从而形成应变最小的单核复合物。通过动力学研究证明了[ML]2+的显著稳定性，结果显示一当量的L1能够在一个两阶段的动力学过程中替代[Fe(terpy)2]2+中的两个2,2′-¶6′,2′′-吡啶（terpy）配体，生成[FeL1]2+。

  DOI：

  10.1039/a907543g

文献信息

• Helicate self-assembly from heterotopic ligand strands of specific binding site sequence
  作者：Virginia C. M. Smith、Jean-Marie Lehn

  DOI：10.1039/cc9960002733

  日期：——

  Linear ligands containing a sequence of three bipyridine B and terpyridine T units form homo- or hetero-nuclear duplex helicates with CuI, CuII and FeII ions; of particular interest is the case of a [(BTB)CuIICuIICuII(TBT)] combination which amounts to the translation of one strand into the other one by virtue of the B–T correspondence established by the five-coordinate CuII ions.

  含有三个联吡啶 B 单元和萜吡啶 T 单元序列的线性配体与 CuI、CuII 和 FeII 离子形成同核或异核双螺旋结构；特别有趣的是[(BTB)CuIICuIICuII(TBT)]组合，它相当于通过五配位 CuII 离子建立的 B-T 对应关系将一条链转化为另一条链。
• Catalysis of phosphodiester transesterification by Cu(II)-terpyridine complexes with peripheral pendent base groups: Implications for the mechanism
  作者：Shanghao Liu、Andrew D. Hamilton

  DOI：10.1016/s0040-4039(96)02519-1

  日期：1997.2

  In this paper we show that in phosphodiester transesterification catalyzed by copper(II)-terpyridine complexes both the metal-bound hydroxyl group and the peripheral pendent tertiary amino groups can provide general base catalysis. At neutral pH the pendent amino groups dominate the process because the metal-bound hydroxyl group is protonated. However, the metal-bound hydroxyl group is more effective at high pH, probably due to its higher basicity and/or closer location to the bound substrate. (C) 1997, Elsevier Science Ltd.
• Metal templated receptors for the effective complexation of dicarboxylates
  作者：M.Scott Goodman、Vrej Jubian、Andrew D. Hamilton

  DOI：10.1016/0040-4039(95)00337-c

  日期：1995.4

  In this paper we show that a thiourea-functionalized terpyridine unit can be induced to form, in the presence of ruthenium (II), a well-ordered recognition site for dicarboxylate ions. Strong binding to the self-assembled receptor can be followed by H-1 NMR in DMSO and association constants of >10(4) M(-1) were measured in certain cases.
• Synthesis of two covalently linked bis(2,2′:6′,2″-terpyridine) (terpy) chelating ligands with different length spacers, comparison of the crystal structures of their mononuclear nickel(II) complexes, and kinetic and mechanistic studies of the reaction of one ligand with [Fe(terpy)2]2+
  作者：Gleb U. Priimov、Peter Moore、Philip K. Maritim、Pamela K. Butalanyi、Nathaniel W. Alcock

  DOI：10.1039/a907543g

  日期：——

  Two new covalently linked bis(2,2′∶6′,2′′-terpyridine)-chelating hexadentate ligands, 1,3-bis(2,2′∶6′,2′′-terpyridyl-5-ylmethylsulfanyl)propane (L1), and 1,4-bis(2,2′∶6′,2′′-terpyridyl-5-ylmethylsulfanyl)butane (L2), and their six-coordinate mononuclear metal complexes [ML][PF6]2 (M = Fe and Ni; L = L1 and L2) have been prepared and characterised. The X-ray structures of [NiL](PF6)2 (L = L1 and L2) have been compared to establish that L2 has the optimum length of linker to give the least strained mononuclear complex. The marked stability of [ML]2+ is demonstrated by kinetic studies that show that one equivalent of L1 is capable of substituting both 2,2′∶6′,2′′-terpyridine (terpy) ligands of [Fe(terpy)2]2+ to give [FeL1]2+ in a two stage kinetic process.

  两种新型共价连接的双(2,2′-¶6′,2′′-吡啶)-螯合六齿配体，1,3-二(2,2′-¶6′,2′′-吡啶-5-基甲基硫醇)丙烷（L1）和1,4-二(2,2′-¶6′,2′′-吡啶-5-基甲基硫醇)丁烷（L2），以及它们的六配位单核金属复合物[ML][PF6]2（M = Fe 和 Ni; L = L1 和 L2）已被合成和表征。通过比较[NiL](PF6)2（L = L1 和 L2）的X射线结构，确认L2具有最佳的连接长度，从而形成应变最小的单核复合物。通过动力学研究证明了[ML]2+的显著稳定性，结果显示一当量的L1能够在一个两阶段的动力学过程中替代[Fe(terpy)2]2+中的两个2,2′-¶6′,2′′-吡啶（terpy）配体，生成[FeL1]2+。
• Messages in Molecules: Ligand/Cation Coding and Self-Recognition in a Constitutionally Dynamic System of Heterometallic Double Helicates
  作者：Annie Marquis、Virginia Smith、Jack Harrowfield、Jean-Marie Lehn、Haiko Herschbach、Rossella Sanvito、Emmanuelle Leize-Wagner、Alain Van Dorsselaer

  DOI：10.1002/chem.200600143

  日期：2006.7.17

  Double helicates are known to exhibit self-recognition characteristics determined by the coordination geometry of the metal involved as well as by the topicity of the ligands. Combining tridentate (terpyridine, T) or bidentate (bipyridine, B) subunits in a tritopic strand affords a set of ligands able to assemble by pairs to form double helicates, homo- or heterostranded, homo- or heterotopic, depending

  已知双螺旋结构具有自我识别特性，该特征是由所涉及的金属的配位几何形状以及配体的局部性决定的。在三位链中结合三齿（三联吡啶，T）或二齿（联吡啶，B）亚基，可以提供一组能够成对组装以形成双螺旋，同或异链，同或异位的配体，具体取决于涉及的金属。四个配体链BBB，TTT，BBT和TBT与金属离子Cu（I），Cu（II）和Zn（II）构成了双螺旋结构的动态组。这些螺旋分别对应于四，五和六配位的Cu（I），Cu（II）和Zn（II）阳离子的BB，BT和TT对正确编码。