1,3,5-tris(2-chlorophenyl)-1,3,5-triazine | 83734-36-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,3,5-tris(2-chlorophenyl)-1,3,5-triazine
• 英文别名: 1,3,5-tris-(2-chloro-phenyl)-hexahydro-[1,3,5]triazine；1,3,5-Tris-(2-chlor-phenyl)-hexahydro-[1,3,5]triazin；1,3,5-Tris(2-chlorophenyl)-1,3,5-triazinane
• CAS: 83734-36-5
• 化学式: C₂₁H₁₈Cl₃N₃
• 分子量: 418.753
• InChiKey: HYEGHLWDSBDKLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  9.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3,5-tris(2-chlorophenyl)-1,3,5-triazine 、 氯羰基亚磺酰氯 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  A Convenient Synthesis of 3-Chloromethyl-2(3H)-benzothiazolones

  摘要：

  以 1,3,5-三苯基-1,3,5-三嗪 2 和氯羰基磺酰氯为原料，采用一锅法合成了 3-氯甲基-2(3H)-苯并噻唑酮 4。4 中的氯原子被醋酸钾、对甲苯硫酚离子和叠氮化钠三种亲核剂所取代，收率良好。

  DOI：

  10.1055/s-1988-27616
• 作为产物：
  描述：

  (2-Chloroanilino)methanol 生成 1,3,5-tris(2-chlorophenyl)-1,3,5-triazine
  参考文献：
  名称：

  PERNYESZI, JOZSEF;BAGI, LASZLO, NEHEZVEGYIP. KUT. INTEZ. KOZL., 17,(1986) 155-170

  摘要：

  DOI：

文献信息

• Preparation of spiro[imidazolidine-4,3′-indolin]-2′-imines <i>via</i> copper(<scp>i</scp>)-catalyzed formal [2 + 2 + 1] cycloaddition of 3-diazoindolin-2-imines and triazines
  作者：Yuxuan Zhou、Fanghui Ma、Ping Lu、Yanguang Wang

  DOI：10.1039/c9ob01767d

  日期：——

  We report a facile and efficient synthesis of spiro[imidazolidine-4,3′-indolin]-2′-imines via a copper(i)-catalyzed cascade reaction of 3-diazoindolin-2-imines with 1,3,5-triazines.

  我们报告了一种简便高效的合成方法，通过铜（i）催化的3-重氮吲哚啉-2-亚胺与1,3,5-三嗪的级联反应合成螺[咪唑啉-4,3'-吲哚]-2'-亚胺。
• Synthesis of Diversely Substituted Imidazolidines <i>via</i> [3+2] Cycloaddition of 1,3,5‐Triazinanes with Donor‐Acceptor Aziridines and Their Anti‐Tumor Activity
  作者：Zhichao Shi、Tingting Fan、Xun Zhang、Feng Zhan、Zhe Wang、Lei Zhao、Jin‐Shun Lin、Yuyang Jiang

  DOI：10.1002/adsc.202001569

  日期：2021.5.18

  cycloaddition of 1,3,5-triazinanes with donor-acceptor aziridines has been developed, accessing diversely substituted imidazolidines high efficiency. Mechanistic investigations support the formation of imidazolidines through an SN1-like pathway. Furthermore, these imidazolidines exhibit promising anti-tumor activity against a series of human cancer cell lines.

  已经开发了AY（OTf）3催化的供体-受体氮丙啶与1,3,5-三嗪并[3 + 2]环加成反应，可高效获得各种取代的咪唑烷。机理研究支持通过S N 1样途径形成咪唑烷。此外，这些咪唑烷类化合物显示出对一系列人类癌细胞系的有希望的抗肿瘤活性。
• <i>N</i>-Nitroso-<i>N</i>-(<i>n</i>-butoxymethyl)arylamines
  作者：Giancarlo Verardo、Angelo G. Giumanini、Fausto Gorassini、Paolo Strazzolini

  DOI：10.1246/bcsj.68.1361

  日期：1995.5

  The title compounds were promptly obtained in fair to good yields as distillable liquids by admixing 1,3,5-triarylhexahydro-1,3,5-triazines (1) with n-butyl nitrite (2) in anhydrous CH2Cl2 and were fully characterized by 1H and 13C NMR, IR, and MS. The pure products were invariably made up of geometric isomers which did not interconvert rapidly at room temperature. o-Substituents could cause difficulties in the free rotations of the aryl substituent about the C–N bond as well of the α-butoxymethyl group. The reaction is believed to occur on the monomeric imines derived from the thermal equilibration of their trimeric and dimeric precursors. Aliphatic hexahydrotriazines were found to be unreactive under the present conditions.

  标题化合物以适中的至良好的产率迅速获得，作为可蒸馏液体，通过在无水CH2Cl2中将1,3,5-三芳基六氢-1,3,5-三嗪（1）与正丁基亚硝酸酯（2）混合，并通过1H和13C NMR、IR和质谱进行了全面表征。纯产品始终由几何异构体组成，这些异构体在室温下不会快速相互转化。邻位取代基可能会导致芳基取代基绕C–N键的自由旋转和α-丁氧基甲基团的自由旋转出现困难。反应被认为发生在从其三聚体和二聚体前体的热平衡中衍生的单体亚胺上。在现有条件下，脂肪族六氢三嗪被发现不活泼。
• Synthesis of α‐Amino Tertiary Alkylperoxides by Lewis Acid‐Catalyzed Peroxidation of 1,3,5‐Triazines
  作者：Lijuan Liu、Zhichao Shi、Xun Zhang、Feng Zhan、Jin‐Shun Lin、Yuyang Jiang

  DOI：10.1002/asia.202100833

  日期：2021.11.2

  Zn(OTf)2-catalyzed peroxidation of 1,3,5-triazines has been developed, accessing diversely substituted α-amino tertiary alkylperoxides with high efficiency under mild conditions. Moreover, the three-component reaction of amine, hydroperoxide, and paraformaldehyde was also proved to give the desired product. Mechanistic investigations and useful synthetic application of the products have also been presented

  已开发出Zn(OTf) 2催化的 1,3,5-三嗪过氧化反应，可在温和条件下高效获得多种取代的 α-氨基叔烷基过氧化物。此外，胺、氢过氧化物和多聚甲醛的三组分反应也被证明可以得到所需的产物。还介绍了产品的机理研究和有用的合成应用。
• Shifting Access from Pyrimidine‐Spirofused to Fused Benzoheterocycles by Modifying the Activated Group Position
  作者：Dezhi Yang、Yan Wang、Chun Zhang、Yun Luo、Xuecheng Zhu、Si Zhao、Wenting Fu、Bin Cheng、Hongbin Zhai、Taimin Wang

  DOI：10.1002/adsc.202301386

  日期：2024.3.8

  The synthesis of pyrimidine‐spirofused indolines from 1,3,5‐triazinanes with 2‐sulfonyliminoindolines has been achieved under catalyst‐ and additive‐free conditions, in which five atoms of 1,3,5‐triazinanes were introduced to the spiro‐annulation products via a (5+1) pathway. Subsequently, this strategy was extended to 3‐aminoindoles and 3‐aminobenzothiophenes, but a different reaction pathway (3+3) was observed. In these cases, three‐atoms of 1,3,5‐triazinanes were incorporated into pyrimidine‐fused indoles/benzothiophenes. These two transformations demonstrate the potential and versatility of 1,3,5‐triazinanes to construct nitrogen‐heterocycles.

  摘要 在无催化剂和添加剂的条件下，实现了由 1,3,5-三嗪酮与 2-磺酰亚胺吲哚合成嘧啶螺烷基吲哚啉，其中 1,3,5-三嗪酮的五个原子通过 (5+1) 途径引入螺烷基化产物。随后，这一策略扩展到 3-氨基吲哚和 3-氨基苯并噻吩，但观察到了不同的反应途径（3+3）。在这些情况下，1,3,5-三嗪酮的三个原子被并入嘧啶融合的吲哚/苯并噻吩中。这两种转化证明了 1,3,5-三嗪酮在构建氮杂环方面的潜力和多功能性。