2,4-dichloro-6-(isopentylthio)-1,3,5-triazine | 92475-37-1

• 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-(isopentylthio)-1,3,5-triazine
• 英文别名: 2,4-Dichloro-6-(3-methylbutylsulfanyl)-1,3,5-triazine；2,4-dichloro-6-(3-methylbutylsulfanyl)-1,3,5-triazine
• CAS: 92475-37-1
• 化学式: C₈H₁₁Cl₂N₃S
• 分子量: 252.167
• InChiKey: PJEHKGHCYSAFPW-UHFFFAOYSA-N

物化性质

• 沸点：
  92-94 °C(Press: 5 x 10)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  64
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-dichloro-6-(isopentylthio)-1,3,5-triazine 在 sodium azide 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.5h， 生成 2-azido-4,6-bis(isopentylthio)-1,3,5-triazine
  参考文献：
  名称：

  研究三正交化学选择性。叠氮化物对三嗪核心的影响

  摘要：

  此处首次报道了三正交化学选择性的一个例子。在这方面，使用三齿s-三嗪作为模型进行了一系列的43个反应。在所有可能的情况下，使用不同的亲核试剂在与生物系统相容的温度下进行三个取代。

  DOI：

  10.1021/acs.orglett.9b02878
• 作为产物：
  描述：

  三聚氯氰 、 异戊硫醇 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以98.1%的产率得到2,4-dichloro-6-(isopentylthio)-1,3,5-triazine
  参考文献：
  名称：

  研究三正交化学选择性。叠氮化物对三嗪核心的影响

  摘要：

  此处首次报道了三正交化学选择性的一个例子。在这方面，使用三齿s-三嗪作为模型进行了一系列的43个反应。在所有可能的情况下，使用不同的亲核试剂在与生物系统相容的温度下进行三个取代。

  DOI：

  10.1021/acs.orglett.9b02878

文献信息

• Phenol as a Modulator in the Chemical Reactivity of 2,4,6-Trichloro-1,3,5-triazine: Rules of the Game II
  作者：Rotimi Sheyi、Anamika Sharma、Ayman El-Faham、Beatriz G. de la Torre、Fernando Albericio

  DOI：10.1071/ch19524

  日期：——

  thiol and amine, were studied and the preferential order of incorporation on TCT was found to be first phenol, second thiol and third amine. The introduction of phenol was achieved at −20°C. The incorporation of this nucleophile in TCT helped to replace the third ‘Cl’ at 35°C, which is compatible with a biological context. The atomic charges on ‘Cl’ calculated by theoretical approaches were consistent

  2,4,6-三氯-1,3,5-三嗪（TCT）是特权核心，具有能够进行连续亲核取代反应的能力。研究了三种亲核试剂，即苯酚，硫醇和胺，发现在TCT上引入的优先顺序为第一酚，第二硫醇和第三胺。在-20℃下引入苯酚。该亲核试剂在TCT中的掺入有助于在35°C取代第三个“ C1”，这与生物学环境相适应。通过理论方法计算得出的“ Cl”上的原子电荷与实验结果一致。
• 1,3,5-Triazine as core for the preparation of dendrons
  作者：Rotimi Sheyi、Anamika Sharma、Ashish Kumar、Ayman El-Faham、Beatriz G. de la Torre、Fernando Albericio

  DOI：10.24820/ark.5550190.p011.245

  日期：——

  A unique property of 2,4,6-trichloro-1,3,5-triazine (TCT) is its ability to undergoes a nucleophilic aromatic substitution reaction (SNAr) under temperature-controlled conditions. Using a convenient and biologically friendly protocol, mono-substituted s-triazines were treated with excess nucleophiles to obtain tri-substituted triazines in 1 + 2 mode (one nucleophile as the first substitution followed by another nucleophile for the other two positions). The nucleophiles used for this study were phenol, thiol and amine, and the best order of incorporation was phenol or thiol for the first position followed by amine for the last two positions.[GRAPHICS].
• Exploiting azido-dichloro-triazine as a linker for regioselective incorporation of peptides through their N, O, S functional groups
  作者：Anamika Sharma、Ashish Kumar、Ayman El-Faham、Beatriz G. de la Torre、Fernando Albericio

  DOI：10.1016/j.bioorg.2020.104334

  日期：2020.11

  In the field of bioconjugation, linker development has witnessed massive growth in recent years. 2,4,6-Trichloro1,3,5-triazine (TCT) is a tridentate linker that can accommodate three distinct nucleophiles. Herein, the reaction of azido triazine derivatives with nucleophiles (amine, thiol and phenol) is studied. The replacement of first chlorine was performed at 0 degrees C while that of the last chlorine was achieved successfully at rt. As a proof of concept of this strategy with potential application in biological studies, pentapeptides (Ac-XGGFL-NH2 where X = Lys or Tyr or Cys) were reacted with 2-azido-4,6-dichlorotriazine to replace the first and second chlorine at 0 degrees C and at rt, respectively. The reactivity of 2-azido-4,6-dichlorotriazine was found to be similar for the alpha and epsilon amine group present in same peptide. These findings demonstrate the applicability of 2-azido-4,6-dichlorotriazine as a linker with potential further application in bioconjugation.
• Investigating Triorthogonal Chemoselectivity. Effect of Azide Substitution on the Triazine Core
  作者：Anamika Sharma、Rotimi Sheyi、Ashish Kumar、Ayman El-Faham、Beatriz G. de la Torre、Fernando Albericio

  DOI：10.1021/acs.orglett.9b02878

  日期：2019.10.4

  triorthogonal chemoselectivity is reported here for the first time. In this regard, a series of 43 reactions were performed using tridentate s-triazine as a model. In all of the possible cases, the three substitutions were carried out using different nucleophiles at a temperature compatible with biological systems.

  此处首次报道了三正交化学选择性的一个例子。在这方面，使用三齿s-三嗪作为模型进行了一系列的43个反应。在所有可能的情况下，使用不同的亲核试剂在与生物系统相容的温度下进行三个取代。