6-chloromethyl-6'-methyl-2,2'-bipyrazine | 162149-12-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-chloromethyl-6'-methyl-2,2'-bipyrazine
• 英文别名: 2-(Chloromethyl)-6-(6-methylpyrazin-2-yl)pyrazine
• CAS: 162149-12-4
• 化学式: C₁₀H₉ClN₄
• 分子量: 220.661
• InChiKey: SGZLKYLHKRPSMB-UHFFFAOYSA-N

物化性质

• 沸点：
  340.8±37.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-chloromethyl-6'-methyl-2,2'-bipyrazine 在 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 48.0h， 生成 6'-methyl-6-[[(6'-methyl-2,2'-bipazin-6-yl)methoxy]methyl]-2,2'-bipyridine
  参考文献：
  名称：

  选择性自组装连续双吡啶-双吡嗪配体链成双链 CuI 螺旋

  摘要：

  在本文中，描述了导致双链螺旋的双齿配位配体的自组装过程的新方面。据报道，CuI 离子自我识别的方向性可能受与精心设计的异位配体中杂环电子构型相关的因素驱动。如果连续的联吡嗪-联​​吡啶配体链 4 与 1 当量反应。CuI 的双金属配合物 [Cu2(L4)2][PF6]2 是在协同过程中形成的。在这种配位化合物中，两条链以相反的方向 (HT) 取向，如 [Cu2(L4)2][PF6]2 的 X 射线结构所示。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

  DOI：

  10.1002/1099-0682(200209)2002:9<2433::aid-ejic2433>3.0.co;2-p
• 作为产物：
  描述：

  2-甲基-6-(6-甲基吡嗪-2-基)吡嗪 在 偶氮二异丁腈 、 1,3,4,6-四氯-3α,6α-二苯基甘脲 作用下， 以 四氯化碳 为溶剂， 以26%的产率得到6-chloromethyl-6'-methyl-2,2'-bipyrazine
  参考文献：
  名称：

  Tris-ACE-α-cyclodextrin tripods: chemistry and metal coordination behaviour

  摘要：

  本研究介绍了通过 "一锅 "施陶丁格-阿扎-维蒂希（SAW）反应合成 C3-对称三-ACE-(6,6â²-双杂环酰)-δ-环糊精的过程。分析了其金属配位化合物的光谱特性。金属超分子螺旋体的自发形成产生了强激子耦合特征，这为了解配合物的性质、几何形状及其绝对构型提供了许多信息。

  DOI：

  10.1039/c3dt51811f

文献信息

• Improved Halogenation of Methyl Aromatics and Methyl Heteroaromatics: Unexpected Reactivity of Tetrahalogeno-diphenylglycolurils
  作者：Florian Moretti、Guillaume Poisson、Alain Marsura

  DOI：10.1002/hc.21314

  日期：2016.5

  exploited in a new direction as reagents for free radical substitution toward some N-halosuccinimide nonreactive bis-heterocycles. An unexpected selectivity and reactivity were observed with methyl benzenes, methyl heterocycles, and methyl-bis-heterocycles of interest. A chemometric study has been performed to optimize five independent factors of the chlorination reaction with TCDGU. The predictive model

  1,3,4,6-四氯 (TCDGU) 和 1,3,4,6-四溴-3α,6α-二苯基甘脲平滑卤素氧化剂已被开发用作自由基取代某些 N-卤代琥珀酰亚胺非反应性试剂的新方向双杂环。对于感兴趣的甲基苯、甲基杂环和甲基双杂环，观察到了意想不到的选择性和反应性。已进行化学计量学研究以优化与 TCDGU 氯化反应的五个独立因素。建立了卤化转化率和一氯化比的预测模型。
• Synthesis and Experimental Electron Density of Bis(heterocyclic) Azines: The Case of 6,6′-Bis(chloromethyl)-2,2′-bipyrazine
  作者：Florence Bodar-Houillon、Youssef Elissami、Alain Marsura、Nour Eddine Ghermani、Enrique Espinosa、Nouzha Bouhmaida、Abdelmalek Thalal

  DOI：10.1002/(sici)1099-0690(199906)1999:6<1427::aid-ejoc1427>3.0.co;2-p

  日期：1999.6

  The synthesis and reactivity of mono- and bis(chloromethyl)-2,2'-bipyrazines toward nucleophiles are reported. The reactivity of the bipyrazine ring is explained in terms of allylic substitution and rearrangement mechanisms. A new family of monofunctionalized bipyrazine derivatives as molecular building blocks for supermolecules has been obtained, opening access to unsymmetrical ligands. The low-temperature crystallographic structure and the experimental electron density distribution of 6,6'-bis(chloromethyl)-2,2'-bipyrazine have been determined on the basis of high-resolution X-ray diffraction data. The electron density of the molecule has been accurately analyzed using the topological properties of its gradient and Laplacian features. The reactivity of these bidentate molecules in metal complexation is related to the shape of the atomic basins and may be explained in terms of a key/lock-type interaction. The results are compared with corresponding data for 2,2'-dimethyl-6,6'-diphenyl-4,4'-bipyrimidine.
• Synthesis and luminescence properties of a new tripode containing 2,2′-bipyrazine subunits: The tris-[(6-methyl-2,2′-bipyrazine-2-yl)methyl]amine
  作者：Florence Bodar-Houillon、Alain Marsura

  DOI：10.1016/0040-4039(94)02381-k

  日期：1995.2

  New 6-methyl-2,2'-bipyrazinyl tripodal ligand 5 and pentadendate ligand 6 have been obtained in a one step alkali metal ion assisted reaction or in two steps from a 6-bipyrazine derivative. Eu(lII) and Tb(III) complexes have been synthesized, UV-Vis spectra show strong absorbance of both complexes at 295nm. Excitation of the Eu(III) complex in acetonitrile causes an emission of Eu3+ ion at 614 nm occuring of the A-ET-E($) process efficiency, preferentially along the transition D-5(0) --> F-7(2).