6-{[1,3-dihydroxy-2-(methyl)prop-2-yl]amino}-2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-4-(piperazin-1-yl)-s-triazine | 1337877-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 6-{[1,3-dihydroxy-2-(methyl)prop-2-yl]amino}-2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-4-(piperazin-1-yl)-s-triazine
• 英文别名: 2-[[4-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)-6-piperazin-1-yl-1,3,5-triazin-2-yl]amino]-2-methylpropane-1,3-diol；2-[[4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-6-piperazin-1-yl-1,3,5-triazin-2-yl]amino]-2-methylpropane-1,3-diol
• CAS: 1337877-27-6
• 化学式: C₁₈H₃₁N₇O₄
• 分子量: 409.489
• InChiKey: PHXZZZUTHZNKBP-UHFFFAOYSA-N

物化性质

• 熔点：
  120.0-126.4 °C
• 沸点：
  695.6±65.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  128
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  三聚氯氰 、 6-{[1,3-dihydroxy-2-(methyl)prop-2-yl]amino}-2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-4-(piperazin-1-yl)-s-triazine 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 23.0h， 以75%的产率得到2-chloro-4,6-bis{4-{6-{[1,3-dihydroxy-2-(methyl)prop-2-yl]amino}-4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-s-triazin-2-yl}-piperazin-1-yl}-s-triazine
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tet.2012.07.096
• 作为产物：
  描述：

  2,4-dichloro-6-(1,3-dihydroxy-2-methylprop-2-yl)-amino-s-triazine 在 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 52.5h， 生成 6-{[1,3-dihydroxy-2-(methyl)prop-2-yl]amino}-2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-4-(piperazin-1-yl)-s-triazine 、 1,4-bis{{6-[1,3-dihydroxy-2-(methyl)prop-2-yl]amino}-4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-s-triazin-2-yl}-piperazine
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tet.2012.07.096

文献信息

• 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.