1-{6-{[1-hydroxy-2-(hydroxymethyl)but-2-yl]amino}-4-{[(4S,5S)-4-(4-nitrophenyl)-1,3-dioxan-5-yl]amino}-s-triazin-2-yl}piperazine | 1414965-72-2

• 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: 1-{6-{[1-hydroxy-2-(hydroxymethyl)but-2-yl]amino}-4-{[(4S,5S)-4-(4-nitrophenyl)-1,3-dioxan-5-yl]amino}-s-triazin-2-yl}piperazine
• 英文别名: 1-{6-{[1-Hydroxy-2-(hydroxymethyl)but-2-yl]amino}-4-{[(4s,5s)-4-(4-nitrophenyl)-1,3-dioxan-5-yl]amino}-s-triazin-2-yl}-piperazine；2-ethyl-2-[[4-[[(4S,5S)-4-(4-nitrophenyl)-1,3-dioxan-5-yl]amino]-6-piperazin-1-yl-1,3,5-triazin-2-yl]amino]propane-1,3-diol
• CAS: 1414965-72-2
• 化学式: C₂₂H₃₂N₈O₆
• 分子量: 504.546
• InChiKey: ZUMQWISKLUKTRY-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  183
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  三聚氯氰 、 1-{6-{[1-hydroxy-2-(hydroxymethyl)but-2-yl]amino}-4-{[(4S,5S)-4-(4-nitrophenyl)-1,3-dioxan-5-yl]amino}-s-triazin-2-yl}piperazine 在 potassium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 42.0h， 以97%的产率得到2-chloro-4,6-bis{4-{{[1-hydroxy-2-(hydroxymethyl)but-2-yl]amino}-4-{[(4S,5S)-4-(4-nitrophenyl)-1,3-dioxan-5-yl]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：

  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 70.0h， 生成 1-{6-{[1-hydroxy-2-(hydroxymethyl)but-2-yl]amino}-4-{[(4S,5S)-4-(4-nitrophenyl)-1,3-dioxan-5-yl]amino}-s-triazin-2-yl}piperazine
  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

• New serinolic amino-s-triazines by chemoselective amination of cyanuric chloride and their (pro)diastereomerism in restricted rotational phenomena
  作者：Oana Moldovan、Pedro Lameiras、Eric Henon、Flavia Popa、Agathe Martinez、Dominique Harakat、Carmen Sacalis、Yvan Ramondenc、Mircea Darabantu

  DOI：10.2478/s11532-012-0015-4

  日期：2012.8.1

  3-dioxanes (“closed-chain” unit). Issued from the restricted rotation about C(s-triazine)-N(exocyclic) partial double bonds, seen as axes of (pro)diastereomerism, a global four-component rotational equilibrium involving the title compounds is discussed based on DFT computation and (VT) NMR data. Depending on π-deficiency of the s-triazine core, an (un)synchronised deblocking of the generated rotational diastereomers

  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。
• Design, iterative synthesis and structure of novel optically active trispiro-dendritic melamines incorporating ‘open-chain’ versus ‘closed-chain’ serinolic peripheral units
  作者：Oana Moldovan、Iulia Nagy、Pedro Lameiras、Cyril Antheaume、Carmen Sacalis、Mircea Darabantu

  DOI：10.1016/j.tetasy.2015.05.003

  日期：2015.7

  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.