N,N',N''-tribenzyl-6,15,24-trimethyl-9,18,27-trihydroxy-2,11,20-triaza<3.3.3>metacyclophane | 145020-77-5

• 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: N,N',N''-tribenzyl-6,15,24-trimethyl-9,18,27-trihydroxy-2,11,20-triaza<3.3.3>metacyclophane
• 英文别名: N,N',N''-tribenzyl-6,15,24-trimethyl-9,18,27-trihydroxy-2,11,20-triaza[3.3.3]metacyclophane；3,11,19-Tribenzyl-7,15,23-trimethyl-3,11,19-triazatetracyclo[19.3.1.15,9.113,17]heptacosa-1(24),5,7,9(27),13(26),14,16,21(25),22-nonaene-25,26,27-triol
• CAS: 145020-77-5
• 化学式: C₄₈H₅₁N₃O₃
• 分子量: 717.951
• InChiKey: DUKLXQLQDKXPKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  54
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  70.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(氯甲基)-2-羟基-5-甲基苯甲醛 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 75.0h， 生成 N,N',N''-tribenzyl-6,15,24-trimethyl-9,18,27-trihydroxy-2,11,20-triaza<3.3.3>metacyclophane
  参考文献：
  名称：

  A Convergent Synthesis of Hexahomotriazacalix[3]arene Macrocycles

  摘要：

  A new, convergent synthesis of hexahomotriazacalix[3] arenes la-e is described. The key transformation in this synthesis involves the coupling of the triamines 4a-d with 2,6-bis(chloromethyl)-4-methylphenol 5 and results in the formation of the hexahomotriazacalix[3] arenes 1a-d in 90-95% yield. The triamines 4a-d were constructed by the one-pot reaction of monochloroaldehyde 3 and a primary amine followed by reduction to yield the triamines 4a-d in 50-55% yield. Deallylation of macrocycle Id was accomplished by palladium catalysis to obtain the N-unsubstituted macrocycle le, which has the potential to be a precursor to a variety of N-substituted hexahomotriazacalix[3] arenes.

  DOI：

  10.1021/jo001094y

文献信息

• Reversible coloring/decoloring reactions of thermochromic leuco dyes controlled by a macrocyclic compound developer
  作者：Sanguansak Sriphalang、Audchara Saenkham、Tawatchai Chaodongbung、Banchob Wanno、Chatthai Kaewtong、Datchanee Pattavarakorn

  DOI：10.1007/s11224-022-01922-2

  日期：2022.8

  were synthesized. Among these macrocyclic compounds, RC4 was determined to be the most appropriate candidate to replace BPA as the developer material used in thermochromic dyes. In tests of prepared thermochromic dyes, RC4 had results similar to those of BPA, achieving the best protonation/deprotonation equilibria and providing a dark contrast with the thermochromic dye. DFT calculations also showed

  在这项研究中，我们检查了大环化合物，以确定它们是否可以为热致变色染料中的 BPA 提供更安全的替代物和稳定的复合物。为实现这一目标，一系列大环化合物，甲基-N-苄基六溴代三氮杂杯[3]芳烃（MeAC3）、对氯-N-苄基六溴代三氮杂杯[3]芳烃（ClAC3）、α-环糊精（α-CD）、合成了β-环糊精（β-CD）、对叔丁基硫杯[4]芳烃（TC4）、杯[4]芳烃（C4）和间苯二酚[4]芳烃（RC4）。在这些大环化合物中，RC4被确定为替代 BPA 作为热致变色染料中使用的显影剂材料的最合适的候选者。在制备的热致变色染料的测试中，RC4的结果与 BPA 相似，达到了最佳的质子化/去质子化平衡，并提供了与热致变色染料的暗对比。DFT 计算还显示RC4和 CVL 之间通过氢键相互作用形成稳定的复合物。
• The first synthesis and properties of hexahomotriazacalix[3]arene
  作者：Hiroyuki Takemura、Kazuhisa Yoshimura、Islam Ullah Khan、Teruo Shinmyozu、Takahiko Inazu

  DOI：10.1016/0040-4039(92)89029-c

  日期：1992.9

  The reaction between 2,6-bis(hydroxylmethyl)-4-methylphenol and benzylamine afforded N,N',N''-tribenzyl-6,15,24-trimethyl-9,18,27-trihydroxy-2,11,20-triaza[3.3.3]metacyclophanes.
• A Convergent Synthesis of Hexahomotriazacalix[3]arene Macrocycles
  作者：Panadda Chirakul、Philip D. Hampton、Zsolt Bencze

  DOI：10.1021/jo001094y

  日期：2000.12.1

  A new, convergent synthesis of hexahomotriazacalix[3] arenes la-e is described. The key transformation in this synthesis involves the coupling of the triamines 4a-d with 2,6-bis(chloromethyl)-4-methylphenol 5 and results in the formation of the hexahomotriazacalix[3] arenes 1a-d in 90-95% yield. The triamines 4a-d were constructed by the one-pot reaction of monochloroaldehyde 3 and a primary amine followed by reduction to yield the triamines 4a-d in 50-55% yield. Deallylation of macrocycle Id was accomplished by palladium catalysis to obtain the N-unsubstituted macrocycle le, which has the potential to be a precursor to a variety of N-substituted hexahomotriazacalix[3] arenes.