5,5'-bis(azidomethyl)-2,2'-bipyridine | 631898-94-7

• 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: 5,5'-bis(azidomethyl)-2,2'-bipyridine
• 英文别名: 2,2'-Bipyridine, 5,5'-bis(azidomethyl)-；5-(azidomethyl)-2-[5-(azidomethyl)pyridin-2-yl]pyridine
• CAS: 631898-94-7
• 化学式: C₁₂H₁₀N₈
• 分子量: 266.265
• InChiKey: VLGOUEZNQJJJIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,5'-bis(azidomethyl)-2,2'-bipyridine 在 palladium on activated charcoal 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以80%的产率得到5,5'-bis(aminomethyl)-2,2'-bipyridine
  参考文献：
  名称：

  通过金属络合物的多价抗生素：有效的二价万古霉素，可抵抗耐万古霉素的肠球菌。

  摘要：

  万古霉素（Van）的二聚体，由一种刚性金属络合物[Pt（en）（H（2）O）（2）]（2+）连接，表现出强大的活性（MIC约0.8杯/ mL，约720倍以上）对抗Vancomycin的肠球菌（VRE）比Van本身更有效。结果表明结合金属络合物和受体/配体相互作用提供了一种构建多价抑制剂的有用方法。

  DOI：

  10.1021/jm030417q
• 作为产物：
  描述：

  5,5'-二溴甲基-2,2'-联吡啶 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 以90%的产率得到5,5'-bis(azidomethyl)-2,2'-bipyridine
  参考文献：
  名称：

  通过金属络合物的多价抗生素：有效的二价万古霉素，可抵抗耐万古霉素的肠球菌。

  摘要：

  万古霉素（Van）的二聚体，由一种刚性金属络合物[Pt（en）（H（2）O）（2）]（2+）连接，表现出强大的活性（MIC约0.8杯/ mL，约720倍以上）对抗Vancomycin的肠球菌（VRE）比Van本身更有效。结果表明结合金属络合物和受体/配体相互作用提供了一种构建多价抑制剂的有用方法。

  DOI：

  10.1021/jm030417q

文献信息

• Double-strand DNA cleavage by copper complexes of 2,2′-dipyridyl with guanidinium/ammonium pendants
  作者：Juan He、Ping Hu、Yu-Jia Wang、Ming-Liang Tong、Hongzhe Sun、Zong-Wan Mao、Liang-Nian Ji

  DOI：10.1039/b801549j

  日期：——

  10−4 M for 2, respectively. The result shows that their cleavage efficiency is about 10-fold higher than the simple analogue [Cu(bipy)Cl2] (3) (0.50 h−1, 3.5 × 10−4 M). The pH dependence of DNA cleavage by 1 and its hydroxide species in solution indicates that mononuclear [Cu(L1)(OH)(H2O)]3+ ion is the active species. Highly effective DNA cleavage ability of 1 is attributed to the effective cooperation

  带有胍基的两个配体/铵盐 团体 被合成，他们的 铜络合物[Cu（L 1）Cl 2 ]（ClO 4）2 ·H 2 O（1）和[Cu（L 2）Cl 2 ]（ClO 4）2（2）（L 1 =5,5'-二[1-（胍基）甲基] -2,2'-联吡啶基阳离子和L 2 =5,5'-二[1-（氨基）甲基] -2,2'-联吡啶基 阳离子），准备充当 核酸酶 模仿。 X射线分析 透露 铜（II）1中的离子具有平面正方形CuN 2 Cl 2-构型。两者之间的最短距离氮 胍和 铜 原子为6.5408（5）Å，与相邻的磷酸二酯的重合 脱氧核糖核酸（大约6Å）。在没有还原剂的情况下，超螺旋质粒 脱氧核糖核酸 进行了复合物的裂解，并证明了它们的水解机制。 自由基清除剂 和T4 连接酶。伪米氏动力学参数（ķ猫，ķ中号）分别计算为4.42ħ -1，7.46×10 -5 M代表1，和4.21ħ -1，1.07×10 -4 M表
• Efficient synthesis of a labile copper(I)-rotaxane complex using click chemistry
  作者：Pierre Mobian、Jean-Paul Collin、Jean-Pierre Sauvage

  DOI：10.1016/j.tetlet.2006.05.024

  日期：2006.7

  Copper(I)-induced threading of 5,5′-diazidomethyl-2,2′-bipyridine through a coordinating ring followed by reaction of a propargyl ether attached to a stopper group leads to the desired rotaxane in 62% yield. The reaction is carried out under the ‘click chemistry’ conditions with 0.75 equiv of additional copper(I).

  铜（I）引起的5,5'-二氮杂甲基-2,2'-联吡啶通过配位环的穿环，接着是与终止基连接的炔丙基醚的反应，以62％的收率得到所需的轮烷。该反应在“点击化学”条件下用0.75当量的额外铜（I）进行。
• Formation and Transmetalation Mechanisms of Homo- and Heterometallic (Fe/Zn) Trinuclear Triple-Stranded Side-by-Side Helicates
  作者：Bidyut Akhuli、Luca Cera、Barun Jana、Subrata Saha、Christoph A. Schalley、Pradyut Ghosh

  DOI：10.1021/ic502855g

  日期：2015.5.4

  A novel linear hybrid tris-bidentate neutral ligand having 2,2'-bipyridine and two terminal triazolylpyridine coordination sites (L) was efficiently synthesized and explored in the synthesis of trinuclear triple-stranded homometallic side-by-side helicates L3Fe3(OTf)(6) (1) and L3Zn3(OTf)(6) (2), in which the three metal centers display alternating Lambda and Delta configurations. Selective formation of the analogous heterometallic side-by-side helicate L3Fe2Zn(OTO)(6) (3) was achieved from a mixture of L, Fe(CH3CN)(2)(OTf)(2), and Zn(OTf)(2) (1:1:1) in acetonitrile at room temperature. Various analytical techniques, i.e., single-crystal X-ray diffraction and NMR and UV/vis spectroscopy, were used to elucidate the sequence of the metal atoms within the heterometallic helicate, with the Zn2+ at the central position. The formation of 3 was also achieved starting from either L3Zn3(OTf)(2) or L3Fe3(OTf)(2) by adding Fe(CH3CN)(2)(OTf2) or Zn(OTf2, respectively. ESI-MS and 11-1 NMR studies elucidated different transmetalation mechanisms for the two cases: While a Zn2+-to-Fe2+ transmetalation occurs by the step-wise exchange of single ions on the helicate L3Zn3(OTf)(6) at room temperature, this mechanism is almost inoperative for the Fe2+ -to Zn2+ transmetalation in L3Fe3(OTf)(2), which is kinetically trapped at room temperature. In contrast, dissociation of L3Fe3(OTf)(2) at higher temperature is required, followed by reassembly to give L3Fe2Zn(OTf)(6). The reassembly follows an interesting mechanistic pathway when an excess of Zn(OTf)(2) is present in solution: First, L3Zn3(OT)(6) forms as the high-temperature thermodynamic product, which is then slowly converted into the thermodynamic heterometallic L3Fe2Zn(OTf)(6) product at room temperature. The temperature-dependent equilibrium shift is traced back to significant entropy differences resulting from an enhancement of the thermal motion of the ligands at high temperature, which destabilize the octahedral iron terminal complex and select zinc in a more stable tetrahedral geometry.
• Synthesis of new copper(I)-complexed rotaxanes via click chemistry
  作者：Stéphanie Durot、Pierre Mobian、Jean-Paul Collin、Jean-Pierre Sauvage

  DOI：10.1016/j.tet.2008.05.078

  日期：2008.9

  The Cu(I)-catalyzed dipolar cycloaddition of azides and terminal alkynes ('click' chemistry) has been used as a mild and efficient stoppering reaction for the preparation of new copper(I)-complexed rotaxanes. (C) 2008 Elsevier Ltd. All rights reserved.
• Multivalent Antibiotics via Metal Complexes:  Potent Divalent Vancomycins against Vancomycin-Resistant Enterococci
  作者：Bengang Xing、Chun-Wing Yu、Pak-Leung Ho、Kin-Hung Chow、Terence Cheung、Hongwei Gu、Zongwei Cai、Bing Xu

  DOI：10.1021/jm030417q

  日期：2003.11.1

  Dimers of vancomycin (Van), linked by a rigid metal complex, [Pt(en)(H(2)O)(2)](2+), exhibit potent activities (MIC approximately 0.8 mug/mL, approximately 720 times more potent than that of Van itself) against vancomycin-resistant enterococci (VRE). The result suggests that combining metal complexation and receptor/ligand interaction offers a useful method to construct multivalent inhibitors.

  万古霉素（Van）的二聚体，由一种刚性金属络合物[Pt（en）（H（2）O）（2）]（2+）连接，表现出强大的活性（MIC约0.8杯/ mL，约720倍以上）对抗Vancomycin的肠球菌（VRE）比Van本身更有效。结果表明结合金属络合物和受体/配体相互作用提供了一种构建多价抑制剂的有用方法。