2-chloro-4,6-bis(4-oxopiperidin-1-yl)-s-triazine | 1055876-19-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-chloro-4,6-bis(4-oxopiperidin-1-yl)-s-triazine
• 英文别名: 2-chloro-4,6-bis(piperidin-4-on-1-yl)-1,3,5-triazine；1-[4-Chloro-6-(4-oxopiperidin-1-yl)-1,3,5-triazin-2-yl]piperidin-4-one
• CAS: 1055876-19-1
• 化学式: C₁₃H₁₆ClN₅O₂
• 分子量: 309.755
• InChiKey: UFCSFZCVECKKSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-chloro-4,6-bis(4-oxopiperidin-1-yl)-s-triazine 在 sodium tetrahydroborate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Potential antibacterial activity of triazine dendrimer: Synthesis and controllable drug release properties

  摘要：

  A novel sustained release delivery system of ciprofloxacin was developed. The system consists of a viscosity enhancer plus a penetration enhancer to overcome penetration barriers and loss due to washout and thus achieve the desired ciprofloxacin ocular absorption. A macromolecule of piperazine core 1,3,5-triazine dendrimer with eight molecules of ciprofloxacin drug as a surface moiety has been synthesized in five steps. Antibacterial activities of this compound have been investigated for Gram-positive and Gram-negative bacteria like Staphylococcus aureus (mtcc 737), Bacillus subtilis (mtcc 2063), Escherichia coli (mtcc-443), Pseudomonas aeruginosa (mtcc 741) and Proteus mirabilis (mtcc425). It was observed that the influence of hydrophobic and hydrophilic balance per repeat unit of these dendrimer has profound effects for antibacterial activities. The MIC value of the compound very lower at 100 mu g/mL(-1) when compared with standard ciprofloxacin at 500 mu g/mL(-1). The compound (10) exhibits five times higher activity against tested organisms when compared with ciprofloxacin as standard. The structures of the dendrimers were determined by means of MALDI-TOF MS, NMR and IR studies. The in vitro release of ciprofloxacin from obtained dendrimer was investigated. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.06.009
• 作为产物：
  描述：

  C₁₃H₂₀ClN₅O₂ 在 叔丁基过氧化氢 作用下， 以 neat (no solvent) 为溶剂， 反应 1.0h， 以92%的产率得到2-chloro-4,6-bis(4-oxopiperidin-1-yl)-s-triazine
  参考文献：
  名称：

  一种协同磁性可回收无机-有机杂化金属氧化物催化剂，用于醇类选择性氧化成醛类和酮类

  摘要：

  协同无机-有机杂化物：在本文中，我们报告了一种协同二氧化硅涂覆的磁性 Fe 3 O 4催化剂，该催化剂用富氮有机部分功能化并固定有钴金属离子 (FNP-5)，用于使用叔选择性氧化醇为醛和酮-丁基氢过氧化物 (TBHP) 作为氧化剂。当前协议的显着特点包括整洁的反应条件、高 TOF 值、产品的可扩展性和低 E 因子值 (1.92)。

  DOI：

  10.1002/cctc.202101262

文献信息

• Serinolic amino-s-triazines: iterative synthesis and rotational stereochemistry phenomena as N-substituted derivatives of 2-aminopropane-1,3-diols
  作者：Monica Pintea、Marijana Fazekas、Pedro Lameiras、Ionut Cadis、Camelia Berghian、Ioan Silaghi-Dumitrescu、Flavia Popa、Constantin Bele、Nelly Plé、Mircea Darabantu

  DOI：10.1016/j.tet.2008.06.071

  日期：2008.9

  The iterative synthesis of 2,4,6-triamino-s-triazines (melamines), precursors and dendritic structures, by amination of cyanuric chloride with C-1 versus C-2-substituted 2-aminopropane-1,3-diols (serinols), is comparatively examined. The stereochemistry of the resulting serinolic amino-s-triazines, issued from the restricted rotation about the newly created C(s-triazine)–N bonds, is for the first time

  用C -1和C -2-取代的2-氨基丙烷-1,3-二醇（丝氨酸）与C -1取代的氰尿酰氯的胺化反应合成2,4,6- triamino - s -triazines（三聚氰胺），前体和树状结构），经过比较检查。由于基于DNMR和DFT计算的（原）非对映异构性，首次讨论了新产生的C（s-三嗪）-N键的受限旋转所产生的丝氨酸氨基s-三嗪的立体化学。数据。
• Amino-<i>s</i>-triazines — Synthesis and stereochemistry of restricted rotational phenomena — First use of a C-2-substituted serinol in tandem with masked 4-piperidone for selective amination of cyanuric chloride
  作者：Flavia Popa、Pedro Lameiras、Eric Henon、Oana Moldovan、Agathe Martinez、Carmen Bâtiu、Yvan Ramondenc、Mircea Darabantu

  DOI：10.1139/v11-075

  日期：2011.10

  Starting from 4-piperidone monohydrate hydrochloride (or the hydrochloride of its ethylene ketal) alone, otherwise in tandem with a C-2-substituted 2-aminopropane-1,3-diol (“serinol”) as amino-nucleophiles in reaction with cyanuric chloride, the synthesis of novel N-substituted amino-s-triazines is reported. The stereochemistry of rotational phenomena occurring about the newly created C(s-triazine)–N< (exocyclic) partial double bonds in the title compounds, seen as new dendritic building blocks, is discussed.

  从4-哌啶酮单水合盐盐酸盐（或其乙烯缩醛的盐酸盐）开始，否则与C-2-取代的2-氨基丙烷-1,3-二醇（“丝氨醇”）一起，在与异氰酸氯反应中作为氨基亲核试剂，报道了新型N-取代氨基-s-三嗪的合成。讨论了在标题化合物中新建立的C（s-三嗪）-N<（外环）部分双键周围发生的旋转现象的立体化学，这被视为新的树突状构建模块。
• Design, synthesis and structure of new dendritic melamines. First use of a tandem C-2-substituted serinol—O,O-masked 4-piperidone as a peripheral unit in iterative synthesis
  作者：Flavia Popa、Pedro Lameiras、Oana Moldovan、Maria Tomoaia-Cotisel、Eric Henon、Agathe Martinez、Carmen Sacalis、Aurora Mocanu、Yvan Ramondenc、Mircea Darabantu

  DOI：10.1016/j.tet.2012.07.096

  日期：2012.10

  The iterative chemoselective amination of cyanuric chloride to dimers of new G-2 dendritic N-substituted-2,4,6-triamino-s-triazines (melamines) having C-2-substituted 2-aminopropane-1,3-diols ('serinols') in tandem with the ethylene ketal of 4-piperidone as peripheral units is reported. The structure as a function of increasing molecular size was studied by NMR spectroscopy, DFT calculation and AFM imaging. A concise nomenclature defining the restricted rotational phenomena about the newly created C(s-triazine)-N(exocyclic) partial double bonds, seen as axes of (pro)diastereomerism, is used. We propose a new form of frontier rotamerism for the dendrimer surface, which operates over a long range. (C) 2012 Elsevier Ltd. All rights reserved.