2,4-dichloro-6-(1-hydroxy-2-(hydroxymethyl)but-2-ylamino)-s-triazine | 60819-40-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 2,4-dichloro-6-(1-hydroxy-2-(hydroxymethyl)but-2-ylamino)-s-triazine
• 英文别名: 2-(4,6-dichloro-[1,3,5]triazin-2-ylamino)-2-ethyl-propane-1,3-diol；2-[(4,6-Dichloro-1,3,5-triazin-2-yl)amino]-2-ethylpropane-1,3-diol
• CAS: 60819-40-1
• 化学式: C₈H₁₂Cl₂N₄O₂
• 分子量: 267.115
• InChiKey: UUHXBHGZHZXDSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  91.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4-dichloro-6-(1-hydroxy-2-(hydroxymethyl)but-2-ylamino)-s-triazine 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 111.0h， 生成 2-chloro-4,6-bis{4-{{[1-hydroxy-2-(hydroxymethyl)but-2-yl]amino}-4-{[(2R,4S,5S)-5-(dimethylamino)-4-(4-nitrophenyl)-1,3-dioxan-2-yl-methyl]amino}-s-triazin-2-yl}-piperazin-1-yl}-s-triazine
  参考文献：
  名称：

  Design, iterative synthesis and structure of novel optically active trispiro-dendritic melamines incorporating ‘open-chain’ versus ‘closed-chain’ serinolic peripheral units

  摘要：

  Starting from commercial C-2-substituted 2-aminopropane-1,3-diols (serinols, 'open-chain' peripheral units) and optically active amino-1,3-dioxanes ('closed-chain' peripheral units) as cycloacetals of (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol (p-nitrophenylserinol) or its 2-dimethylamino analogue, we herein report a new series of di- and trimeric G-1 trispiro-dendritic melamines, they were synthesised convergently by iterative chemoselective amination of cyanuric chloride. Depending on the number of hydroxymethyl groups in the 'open-chain' peripheral unit and the type of the rigid amino-anchorage (axial or equatorial) of the 'closed-chain' counterpart, the classic restricted rotation about the C(s-triazine)-N(exocyclic) partial double bonds induced, progressively, specific spatial arrangements in angularly connected G-0 and G-1 dendrons, including axial chirality in G-1 dimeric or G-1 trimeric melamines. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.05.003
• 作为产物：
  描述：

  三聚氯氰 、 2-氨基-2-乙基-1,3-丙二醇 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 2,4-dichloro-6-(1-hydroxy-2-(hydroxymethyl)but-2-ylamino)-s-triazine
  参考文献：
  名称：

  氰尿酰氯化学选择性胺化的新型丝氨酰氨基-s-三嗪及其在受限旋转现象中的（前）非对映异构

  摘要：

  摘要报道了高度化学选择性制备新的 N-不对称取代的氯二氨基-s-三嗪和三聚氰胺，被视为迭代合成的基础。它由氰尿酰氯与商用 C-2-取代的 2-氨基丙烷-1,3-二醇（“丝氨醇”）胺化组成，起到“开链”单元和对映纯（1S,2S）-2-氨基的作用-1-（4-硝基苯基）丙烷-1,3-二醇（“对硝基苯基丝氨醇”）基于氨基-1,3-二恶烷（“闭链”单元）。从关于 C(s-三嗪)-N(环外)部分双键的受限旋转发出，被视为（原）非对映异构的轴，基于 DFT 计算和（VT）讨论了涉及标题化合物的全局四组分旋转平衡)核磁共振数据。取决于 s-三嗪核的 π 缺陷，观察到生成的旋转非对映异构体的（非）同步解封闭。它们被讨论为内部与内部的影响。分子间NH ... OH（动态）相互作用发生在“开链”单元和“闭链”单元的anancomeric、轴向与赤道、氨基锚定。

  DOI：

  10.2478/s11532-012-0015-4

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.
• KRAJZ B. O.; REMIZOV A. L., ZH. ORGAN. XIMII, 1979, 15, HO 6, 1282-1289
  作者：KRAJZ B. O.、 REMIZOV A. L.

  DOI：——

  日期：——