2-([3-tert-butoxycarbonylaminophenyl]amino)-4,6-dichloro[1,3,5]triazine | 537049-05-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-([3-tert-butoxycarbonylaminophenyl]amino)-4,6-dichloro[1,3,5]triazine
• 英文别名: 2,4-dichloro-6-(3-N-1-tert-butoxycarbonylaminophenyl)amino-1,3,5-triazine；2,4-dichloro-6-(3-N-tert-butoxycarbonylamino)phenylamino-1,3,5-triazine；tert-butyl N-[3-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]phenyl]carbamate
• CAS: 537049-05-1
• 化学式: C₁₄H₁₅Cl₂N₅O₂
• 分子量: 356.211
• InChiKey: TZGFQWFQSUPXOS-UHFFFAOYSA-N

物化性质

• 熔点：
  172-173 °C
• 密度：
  1.435±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  89
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-([3-tert-butoxycarbonylaminophenyl]amino)-4,6-dichloro[1,3,5]triazine 在 碳酸氢钠 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 生成 benzyl N-[3-[[4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]anilino]-6-(pentylamino)-1,3,5-triazin-2-yl]amino]phenyl]carbamate
  参考文献：
  名称：

  Synthesis of novel rigid triazine-based calix[6]arenes

  摘要：

  In this report, the stepwise synthesis of a novel rigid and functionalised macrocycle 2 based on triazine and phenylenediamine linkers, is presented. Poor recognition of the macrocycle 2 for its substrates is observed, which shows experimentally that for the meltriazine based-calix[6]arene system, the binding ability of the melamine moiety gets more benefit from the ring flexibility derived from a xylenediamine linker 1 than from a phenylenediamine linker 2. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02884-8
• 作为产物：
  描述：

  三聚氯氰 、 N-Boc-间苯二胺 在 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 3.5h， 以99.6%的产率得到2-([3-tert-butoxycarbonylaminophenyl]amino)-4,6-dichloro[1,3,5]triazine
  参考文献：
  名称：

  N，N'-双（4,6-二取代的1,3,5-三嗪-2-基）-4-氨基苯乙胺的有效千克级合成

  摘要：

  开发了一种实用的大规模合成方法，用于制备以化合物2为例的N，N′-双（4,6-二取代的1,3,5-三嗪-2-基）-4-氨基苯乙胺衍生物。基于三嗪环上三个氯原子的反应性差异，该途径是六步过程，从市售的氰尿酰氯和3-（叔丁氧基羰基氨基）苯胺开始。按比例扩大优化程序，以最终产品2的总收率达到61％和99.9％的纯度。这些低分子量化合物模拟蛋白质A与IgG抗体结合的能力。

  DOI：

  10.1021/op900202b

文献信息

• [EN] 2,4,6-TRIAMINO-S-TRIAZINE-BASED COMPOUNDS WHICH BIND TO THE TAIL (Fc) PORTION OF IMMUNOGLOBULINS AND THEIR USE<br/>[FR] COMPOSÉS À BASE DE 2,4,6-TRIAMINO-S-TRIAZINE RELIÉS À LA PARTIE DE QUEUE (Fc) DES IMMUNOGLOBULINES ET LEUR UTILISATION
  申请人：PROMETIC BIOSCIENCES INC

  公开号：WO2006024175A1

  公开（公告）日：2006-03-09

  The present invention comprises new compounds described by the following general formula:(I) NH2 where R is a straight chain or cyclic alkyl group, X is oxygen or sufur or an imino group or is absent, R' is an amino or metoxy group, or fluorine or chlorine atom and n is 0, 1 or 2. These compounds are useful for binding to tail or Fc portion of immunoglobulins and so have utility in those applications which require the non-covalent binding interaction of a molecule with the Fc portion of immunoglobulins. Such applications include the detection and purification of immunoglobulins as well as the treatment of certain autoimmune diseases.

  本发明包括以下一般式描述的新化合物：（I）NH2，其中R是直链或环烷基，X是氧或硫或亚硝基或不存在，R'是氨基或甲氧基基团，或氟或氯原子，n为0、1或2。这些化合物可用于与免疫球蛋白的尾部或Fc部分结合，因此在需要分子与免疫球蛋白的Fc部分非共价结合相互作用的应用中具有实用性。这些应用包括检测和纯化免疫球蛋白以及治疗某些自身免疫疾病。
• An Efficient Kilogram-Scale Synthesis of <i>N</i>,<i>N</i>′-Bis(4,6-disubstituted 1,3,5-triazin-2-yl)-4-aminophenetylamine
  作者：Jean-Simon Duceppe、Valérie Perron、Josée Cloutier、Christopher Penney、Boulos Zacharie

  DOI：10.1021/op900202b

  日期：2009.11.20

  A practical large-scale synthesis was developed for the preparation of N,N′-bis(4,6-disubstituted 1,3,5-triazin-2-yl)-4-aminophenethylamine derivatives exemplified by compound 2. This route is a six-step procedure starting from commercially available cyanuric chloride and 3-(tert-butoxycarbonylamino) aniline based on the reactivity differences of the three chlorine atoms on the triazine ring. The optimized

  开发了一种实用的大规模合成方法，用于制备以化合物2为例的N，N′-双（4,6-二取代的1,3,5-三嗪-2-基）-4-氨基苯乙胺衍生物。基于三嗪环上三个氯原子的反应性差异，该途径是六步过程，从市售的氰尿酰氯和3-（叔丁氧基羰基氨基）苯胺开始。按比例扩大优化程序，以最终产品2的总收率达到61％和99.9％的纯度。这些低分子量化合物模拟蛋白质A与IgG抗体结合的能力。
• [EN] METHODS TO INCREASE THE DURATION OF ACTION OF THERAPEUTIC MONOCLONAL ANTIBODY PRODUCTS<br/>[FR] UTILISATION DE LIANTS DE PRODUITS D'ANTICORPS MONOCLONAUX À AFFINITÉ ÉLEVÉE POUR AUGMENTER LA DURÉE D'ACTION DE PRODUITS D'ANTICORPS MONOCLONAUX THÉRAPEUTIQUES DANS UN TISSU BIOLOGIQUE
  申请人：UNIV LELAND STANFORD JUNIOR

  公开号：WO2018048941A3

  公开（公告）日：2019-04-25
• 2,4,6-triamino-s-triazine-based compounds which bind to the tail (fc) portion of immunoglobulins and their use
  申请人：Penney Christopher

  公开号：US20090068169A1

  公开（公告）日：2009-03-12

  The present invention describes new compounds which are useful for binding to the tail or Fc portion of immunoglobulins and so have utility in those applications which require the non-covalent binding interaction of a molecule with the Fc portion of immunoglobulins. Such applications include the detection and purification of immunoglobulins as well as the treatment of certain autoimmune diseases.
• Synthesis of novel rigid triazine-based calix[6]arenes
  作者：Xiaoping Yang、Christopher R. Lowe

  DOI：10.1016/s0040-4039(02)02884-8

  日期：2003.2

  In this report, the stepwise synthesis of a novel rigid and functionalised macrocycle 2 based on triazine and phenylenediamine linkers, is presented. Poor recognition of the macrocycle 2 for its substrates is observed, which shows experimentally that for the meltriazine based-calix[6]arene system, the binding ability of the melamine moiety gets more benefit from the ring flexibility derived from a xylenediamine linker 1 than from a phenylenediamine linker 2. (C) 2003 Elsevier Science Ltd. All rights reserved.