2-[5-(溴甲基)吡啶-2-基]-5-甲基吡啶 | 117585-58-7

• 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
• 中文名称: 2-[5-(溴甲基)吡啶-2-基]-5-甲基吡啶
• 中文别名: 5-甲基-5'-溴甲基-2,2'-联吡啶
• 英文名称: 5-bromomethyl-5'-methyl-2,2'-bipyridine
• 英文别名: 5-(bromomethyl)-5′-methyl-2,2′-bipyridine；2,2'-Bipyridine, 5-(bromomethyl)-5'-methyl-；2-[5-(bromomethyl)pyridin-2-yl]-5-methylpyridine
• CAS: 117585-58-7
• 化学式: C₁₂H₁₁BrN₂
• 分子量: 263.137
• InChiKey: NZTFUSADNGXITD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：

  2-[5-(溴甲基)吡啶-2-基]-5-甲基吡啶 在 双(三甲基硫化硅) 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以40%的产率得到(5'-Methyl-[2,2']bipyridinyl-5-yl)-methanethiol
  参考文献：
  名称：

  Functionalized Gold Nanoparticles as Phosphorescent Nanomaterials and Sensors

  摘要：

  Ligand-capped gold nanoparticles were synthesized by capping monothiol derivatives of 2,2'dipyridyl onto the surface of Au nanoparticles (Au-BT). The average size of the metal core is around 4 nm, with a shell of similar to 340 bipyridine ligands around the Au nanoparticle. The high local concentration of the chelating ligands (similar to 5 M) around the Au nanoparticle makes these particles excellent ion sponges, and their complexation with Eu-lll/Tb-lll ions yields phosphorescent nanomaterials. Absorption spectral studies confirm a 1:3 complexation between Eul(lll)/Tb-lll ions and bipyridines, functionalized on the surface of Au nanoparticles. The red-emitting Au-BT:Eu-lll complex exhibits a long lifetime of 0.36 ms with six line-like emission peaks, whereas the green-emitting Au-BT:Tb-lll complex exhibits a lifetime of 0.7 ms with four line-like emission peaks. These phosphorescent nanomaterials, designed by linking BT:Eu-lll complexes to Au nanoparticles, were further utilized as sensors for metal cations. A dramatic decrease in the luminescence was observed upon addition of alkaline earth metal ions (Ca2+, Mg2+) and transition metal ions (Cu2+, Zn2+, Ni2+), resulting from an isomorphous substitution of Eu-lll ions, whereas the luminescence intensity was not influenced by the addition of Na+ and K+ ions. Direct interaction of bipyridine-capped Au nanoparticles with Cu2+ ions brings the nanohybrid systems closer, leading to the formation of three-dimensional superstructures. Strong interparticle plasmon interactions were observed in these closely spaced Au nanoparticles.

  DOI：

  10.1021/ja054347j
• 作为产物：
  描述：

  5 5'-二甲基-2,2'-二吡啶 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， 反应 3.0h， 生成 2-[5-(溴甲基)吡啶-2-基]-5-甲基吡啶
  参考文献：
  名称：

  A three-photon probe with dual emission colors for imaging of Zn(ii) ions in living cells

  摘要：

  本研究开发了一种新型三光子探针，用于对活细胞中的外源锌（II）离子进行成像，该探针在三光子激发下具有不同的发射颜色。在酸的存在下，探针的电荷转移状态和发射颜色的调整也得到了证实。

  DOI：

  10.1039/c4cc05999a

文献信息

• Remarkably Large Positive and Negative Allosteric Effects on Ion Recognition by the Formation of a Novel Helical Pseudocryptand
  作者：Tatsuya Nabeshima、Yuko Yoshihira、Toshiyuki Saiki、Shigehisa Akine、Ernst Horn

  DOI：10.1021/ja028750r

  日期：2003.1.1

  is the first example of an allosteric recognition system, in which the same effector, that is, Fe(II), exhibits both large positive and negative allosteric effects on equilibrium and dynamic recognition events. The X-ray analysis and 1H NMR examination indicate that the combination of the macrobicyclic effect and the intramolecular interchain interactions (CH-pi interaction and steric hindrance) finely

  在超分子化学中，大量注意力集中在通过外部刺激调节客体结合上。然而，为了将相同的效应器用于高度客体选择性的正和负变构效应，需要对主体结构进行更严格和更精确的调节。一种新型变构宿主 1 与 Fe(II) 结合以提供假密码体 1.Fe(II)，它带有一个空腔，该空腔被三个聚醚链以螺旋方式包围。1 (Na+ > K+ > Rb+ > Cs+) 的结合选择性与 1.Fe(II) 相反（Cs+ > Rb+ > K+ > Na+）。通过液膜的单离子传输显示出与平衡常数相似的离子选择性。据我们所知，这是变构识别系统的第一个例子，其中相同的效应物，即 Fe(II)，对平衡和动态识别事件表现出巨大的正负变构效应。X 射线分析和 1H NMR 检查表明，大双环效应和分子内链间相互作用（CH-pi 相互作用和位阻）的结合可以很好地控制正负变构效应，这取决于客体的大小。螺旋框架开辟了一种新的通用方法，用于构建更复杂、可控的螺旋生物分子受体，例如
• Ion Pair-Directed Regiocontrol in Transition-Metal Catalysis: A Meta-Selective C–H Borylation of Aromatic Quaternary Ammonium Salts
  作者：Holly J. Davis、Madalina T. Mihai、Robert J. Phipps

  DOI：10.1021/jacs.6b08164

  日期：2016.10.5

  interactions to direct transition-metal catalysis is a potentially powerful yet relatively underexplored strategy, with most investigations thus far focusing on using hydrogen bonds as the controlling element. We have developed an ion pair-directed approach to controlling regioselectivity in the iridium-catalyzed borylation of two classes of aromatic quaternary ammonium salts, leading to versatile meta-borylated

  使用非共价相互作用直接过渡金属催化是一种潜在的强大但相对未开发的策略，迄今为止大多数研究都集中在使用氢键作为控制元素。我们开发了一种离子对导向的方法来控制铱催化的两类芳族季铵盐的硼化反应中的区域选择性，从而产生多功能的偏硼化产物。通过检查一系列取代的底物，这提供了适合快速多样化的复杂的官能化芳香支架，并更广泛地证明了离子对在过渡金属催化中控制区域化学的可行性。
• A widely applicable concept for predictable induction of preferred configuration in C3-symmetric systems
  作者：Gebhard Haberhauer、Thomas Oeser、Frank Rominger

  DOI：10.1039/b502158h

  日期：——

  Starting from a single chiral platform a widely applicable concept to introduce the preferred configuration of octahedral and tetrahedral centres in C3-symmetric systems is described.

  从单一手性平台出发，描述了一种广泛适用的概念，用于引入 C3 对称系统中八面体和四面体中心的优选构型。
• <i>meta</i> -Selective C−H Borylation of Benzylamine-, Phenethylamine-, and Phenylpropylamine-Derived Amides Enabled by a Single Anionic Ligand
  作者：Holly J. Davis、Georgi R. Genov、Robert J. Phipps

  DOI：10.1002/anie.201708967

  日期：2017.10.16

  Clever positioning: A bipyridine ligand incorporating a remote anionic sulfonate group directs iridium-catalyzed borylation to the meta-position on a range of amide-containing arenes. It is proposed that this selectivity is a result of a hydrogen bonding interaction to correctly position the iridium metal centre in the crucial C−H activation.

  巧妙的定位：结合有远端阴离子磺酸盐基团的联吡啶配体可将铱催化的硼化反应引导至一系列含酰胺芳烃的间位。提出该选择性是氢键相互作用的结果，该氢键相互作用将铱金属中心正确定位在关键的CH活化中。
• Oxidation of α-hydroxy acids by an oxidation-active flavin mimic bearing a bipyridin-6-ylmethyl moiety in the presence of Zn²⁺and a base in tert-butyl alcohol
  作者：Yumihiko Yano、Keita Mitsui、Youichi Ohsawa、Toshitada Kobayashi、Tatsuya Nabeshima

  DOI：10.1039/c39930001719

  日期：——

  A benzo-dipteridine (BDP) having a bipyridin-6-ylmethyl moiety oxidizes α-hydroxy acids to give α-keto acids in the presence of Zn2+ and Et3N in ButOH, whereas a BDP bearing a bipyridin-5-ylmethyl moiety is unable to oxidize them under the same conditions; this is the first example of a D-lactate dehydrogenase model.

  一种具有双吡啶-6-基甲基部分结构的苯并二氢吡啶（BDP）在Zn2+和三乙胺（Et3N）存在下，能够将α-羟基酸氧化为α-酮酸，而具有双吡啶-5-基甲基部分结构的BDP在相同条件下则无法进行氧化；这是D-乳酸脱氢酶模型的第一个例子。