2,5-bis(2-chloro-acetylamino)-pyridine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,5-bis(2-chloro-acetylamino)-pyridine
• 英文别名: N,N'-bis(2-chloroacetamide)-1,3-diaminobenzene；N,N'-bis(2-chloroacetamido)-2,6-diaminopyridine；N,N'-(pyridine-2,6-diyl)bis(2-chloroacetamide)；BCDP；2,6-bis(chloroethylamido)pyridine；2-chloro-N-{6-[(chloroacetyl)amino]-2-pyridinyl}acetamide；2-chloro-N-[6-[(2-chloroacetyl)amino]pyridin-2-yl]acetamide
• 化学式: C₉H₉Cl₂N₃O₂
• mdl: MFCD00226524
• 分子量: 262.095
• InChiKey: KSAZDTMSYSZRSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  71.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-bis(2-chloro-acetylamino)-pyridine 在 Pd/C 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 2-amino-N-[6-[(2-aminoacetyl)amino]pyridin-2-yl]acetamide
  参考文献：
  名称：

  焦磷酸盐选择性荧光化学传感器：模仿DAPI的核染色的级联识别†

  摘要：

  合成了一种新的锌（II）配合物，其中有稠合的羟基萘吡啶（SPHN）作为配位体，用于选择性识别焦磷酸盐（PPi）相对于其他阴离子，包括混合水溶液中的磷酸盐。在细胞内焦磷酸盐的存在下，与Zn 2+离子缔合的SPHN的荧光增强作用被淬灭。在逻辑门的构造中利用了这种现象。SPHN与Zn 2+的结合及其被PPi取代已通过光物理研究建立，并得到DFT研究水平的支持。锌与SPHN结合后{ SPNH–Zn }复合物中蓝色荧光的发展 显示出与在市场上可买到的染色化合物DAPI（二氨基-2-苯基吲哚）相似的细胞核素可用作细胞中的核标记。

  DOI：

  10.1039/c4dt01262c
• 作为产物：
  描述：

  2,6-二氨基吡啶 、 氯乙酰氯 在 三乙胺 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以96%的产率得到2,5-bis(2-chloro-acetylamino)-pyridine
  参考文献：
  名称：

  一种简单且生态兼容的新型对称二硫代氨基甲酸酯 Podands 的一锅合成及其动态核磁共振研究

  摘要：

  摘要 在水中不存在催化剂的情况下，使用胺 (3a-c )、CS2 和二氯二胺 (DCDs) (2a, c ) 进行了一种简单且生态相容的 podands 合成 4a-i。在芳族二胺 (1a, c ) 与氯乙酰氯的反应中获得了三个反应的 DCD (2a-c )。讨论了三个系列 podands（4a-c、4d-f 和 4g-i）的动态核磁共振光谱数据，并计算了它们在聚结温度下的激活自由能（ΔG ≠ cs）。由于硫代酰胺 C-N 键的旋转和共振效应，这些 podands 的 ΔG ≠ c 归因于 14.7-17 kcal/mol 范围内的构象异构化。[本文提供补充材料。转至出版商的在线版 Phosphorus, Sulfer，

  DOI：

  10.1080/10426507.2012.717133

文献信息

• Ditopic bis(<i>N</i>,<i>N</i>′,<i>N</i>′-substituted 1,2-ethanediamine) ligands: synthesis and coordination chemistry
  作者：Andreas Rösch、Christoph M. Herzog、Simon H. F. Schreiner、Helmar Görls、Robert Kretschmer

  DOI：10.1039/d0dt03124k

  日期：——

  The synthesis of two different types of bis(N,N′,N′-substituted 1,2-ethanediamine)s, bridged either through the secondary (type 1) or tertiary (type 2) amine groups is reported. Selected protio-ligands have been applied in subsequent metallation reactions using aluminium, magnesium, tin, and zinc sources allowing to isolate five mononuclear and eight dinuclear complexes. All complexes have been fully

  报道了通过仲胺（1型）或叔胺（2型）桥联的两种不同类型的双（N，N '，N'-取代的1,2-乙二胺）的合成。使用铝，镁，锡和锌源，已选择的蛋白质配体已用于后续的金属化反应中，从而可以分离出五个单核和八个双核配合物。所有配合物均已得到充分表征，并已通过单晶X射线衍射分析研究了其固态结构。13种络合物中的9种带有反应性烷基，酰胺或氢化物基团，这表明它们作为（过渡）金属的催化剂或载体的潜力。
• Synthesis and Template Studies of New Aza Macrocycles and one Cryptand Based on 2,6-diaminopyridine and its Computational NMR Studies Using Density Functional Theory
  作者：Abbas Shockravi、Mahmood Kamali、Hadi Behzadi、Somayeh Pahlavan Moghanlo、Mahdieh Nategholeslam

  DOI：10.2174/1570178611310040006

  日期：2013.5.1

  KI in good to high yields. Also the template effects of cations such as Na+, K+, K+/KI and Cs+ on the reaction yields for macrocycles (4a-c and I, k) were investigated. In this study it is found that size matching and template effect of K+ with KI as catalyst are most suitable for macrocyclization process. The structures of macrocycles and cryptand were confirmed by IR, 1H NMR, 13C NMR and Mass spectroscopies

  新大环化合物10 5 A-CAND EK和一个穴状配体5 d是由二胺的反应合成的化合物4一-K与N，N'-双（2-氯乙酰氨基）-2,6-二氨基吡啶（BCDP）3在K的存在2 CO 3和KI的产率高到高。还研究了诸如Na +，K +，K + / KI和Cs +之类的阳离子对大环化合物（4 a-c和I，k）反应产率的模板作用。在这项研究中，发现K +的大小匹配和模板效应以KI为催化剂最适合大环化工艺。通过IR，1 H NMR，13 C NMR和质谱确认大环和隐链的结构。另外，使用密度泛函理论（DFT）在B3LYP / 6-31G *水平上获得了5d的计算的1 H和13 C NMR参数。发现计算出的化学位移与实验数据一致。
• Synthesis of α-chloroamides in water
  作者：Andrew J. Harte、Thorfinnur Gunnlaugsson

  DOI：10.1016/j.tetlet.2006.06.090

  日期：2006.8

  The reaction between chloroacetyl chloride and mono- or bis-aliphatic or aromatic amines in water under basic or neutral conditions gives rise to the formation of a variety of functionalized alpha-chloroamides. The resulting products were obtained as solids in moderate to good yields, upon precipitation and isolation by filtration. (c) 2006 Elsevier Ltd. All rights reserved.
• Zinc selective chemosensor based on pyridyl-amide fluorescence
  作者：Hong Gyu Lee、Ju Hoon Lee、Seung Pyo Jang、Hyun Min Park、Sung-Jin Kim、Youngmee Kim、Cheal Kim、Roger G. Harrison

  DOI：10.1016/j.tet.2011.08.049

  日期：2011.10

  Chemosensors are developed to image zinc ions. Fluorescence enhancement due to Zn2+ binding is an excellent way to detect its presence. A chemosensor for Zn2+ based on dipicolylamine (DPA) groups connected by a pyridyl amide backbone has been synthesized. Addition of 2-chloroacetyl chloride to 2,6-diaminopyridine affords 2,6-bis(chloroethylamido)pyridine, which is converted to the sensor BADPA-P by 2,2'-dipicolylamine displacement of chlorine. This compound along with two others, the mono-DPA, ADPA-P and the benzyl in place of pyridyl, BADPA-B, present three potential Zn2+ sensors. It was found that BADPA-P in the presence of Zn2+ shows a large increase in fluorescence, whether in polar organic or aqueous environments. Its fluorescence in the presence of Cd2+, unlike with Zn2+, is not enhanced when excited at longer wavelengths. Proton NMR measurements, indicate two Zn2+ ions bind to BADPA-P. Also, Zn2+ enhances fluorescence even when other metal ions are present. (C) 2011 Elsevier Ltd. All rights reserved.
• Complexation of two macrocycles for amide, saccharide, and halide derivatives: the capacity of 1,2,3-triazole as hydrogen and halogen bonding acceptors
  作者：Dong-Yun Wang、Li-Yan You、Ji-Liang Wang、Hui Wang、Dan-Wei Zhang、Zhan-Ting Li

  DOI：10.1016/j.tetlet.2013.10.064

  日期：2013.12

  Two 1,2,3-triazole- and amide-incorporated macrocycles have been prepared by 1,3-dipolar cycloaddition of the corresponding dialkyne and diazide precursors. Intramolecular C-H center dot center dot center dot O hydrogen bonding is introduced to lock the C-5-H atoms of the 1,2,3-triazole rings. The binding of the two macrocycles to amide, monosaccharide, and halide derivatives in chloroform or dichloromethane has been investigated. It is revealed that the amide units dominate their binding toward the amide and monosaccharide guests through forming intermolecular hydrogen bonding and 1,2,3-triazole is as weak as an intermolecular hydrogen bonding acceptor, but it forms intermolecular halogen bonding when cooperative effect exists. (C) 2013 Elsevier Ltd. All rights reserved.