1,3,5-三(1-萘基)-1,3,5-三嗪-2,4,6(1H,3H,5H)-三酮 | 4803-09-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1,3,5-三(1-萘基)-1,3,5-三嗪-2,4,6(1H,3H,5H)-三酮
• 英文名称: 1,3,5(2H,4H,6H)-tri(1-naphthyl)-2,4,6-trioxo-1,3,5-triazine
• 英文别名: 1,3,5-triphenyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione；1,3,5-tris(1-naphthyl)-1,3,5-triazinane-2,4,6-trione；tris(1-naphthyl)isocyanurate；tri-1-naphthyl isocyanurate；1,3,5-tri-naphthalen-1-yl-[1,3,5]triazinane-2,4,6-trione；Tri-[1]naphthyl-[1,3,5]triazintrion；s-Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-tri-1-naphthyl-；1,3,5-trinaphthalen-1-yl-1,3,5-triazinane-2,4,6-trione
• CAS: 4803-09-2
• 化学式: C₃₃H₂₁N₃O₃
• 分子量: 507.548
• InChiKey: FQKAVBQBCGHCDQ-UHFFFAOYSA-N

物化性质

• 熔点：
  340 °C
• 沸点：
  729.0±33.0 °C(Predicted)
• 密度：
  1.394±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  39
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-Alapha-萘异氰酸酯 在 三乙胺 作用下， 以 苯 为溶剂， 100.0 ℃ 、800.0 MPa 条件下， 反应 20.0h， 以85%的产率得到1,3,5-三(1-萘基)-1,3,5-三嗪-2,4,6(1H,3H,5H)-三酮
  参考文献：
  名称：

  高压下异氰酸酯三聚反应合成异氰脲酸酯

  摘要：

  异氰酸苯酯在三乙胺存在下的三聚反应在高压下加速，得到几乎定量的异氰脲酸三苯酯。苯中的反应通过压缩显着加速。考察了压力、温度、催化剂和溶剂对异氰酸苯酯三聚反应的影响。芳基和正烷基异氰酸酯在高压下三聚以良好的产率得到相应的异氰脲酸酯，而具有庞大烷基如叔丁基和环己基的异氰酸酯即使在800 MPa下也不会三聚。

  DOI：

  10.1246/bcsj.63.3486

文献信息

• An Electron-Rich Proazaphosphatrane for Isocyanate Trimerization to Isocyanurates
  作者：Steven M. Raders、John G. Verkade

  DOI：10.1021/jo9023396

  日期：2010.8.6

  synthesis of the new electron-rich, sterically hindered proazaphosphatrane shown above is described herein. This proazaphosphatrane catalyzes the cyclotrimerization of a wide variety of isocyanates to isocyanurates under mild conditions with unprecedentedly fast reaction times, giving moderate to high product yields. It is also shown that this proazaphosphatrane can be recycled up to 5 times.

  本文描述了上面显示的新的富含电子的，空间受阻的原氮杂磷杂环戊烷的简便合成。该原氮杂磷杂环戊烷在温和的条件下以前所未有的快速反应时间催化多种异氰酸酯向异氰脲酸酯的环三聚反应，产生中等至高的产物收率。还显示该原氮杂磷杂环戊烷最多可循环使用5次。
• Haloamidation of alkynes and related reactions using zirconacycles and isocyanates
  作者：Yanzhong Li、Hiroshi Matsumura、Masamichi Yamanaka、Tamotsu Takahashi

  DOI：10.1016/j.tet.2003.08.078

  日期：2004.2

  Zirconacyclopentenes reacted with isocyanates to give aza- or oxazirconacycles which were conveniently coverted into the corresponding haloamidation products of alkynes after halogenation. 1,4-Bistrimethylsilyl substituted zirconacyclopentadiene afforded a low yield of iodoamidation product, whereas zirconium–alkyne complexes stabilized with phosphine gave the iodoamidation products in moderate yields

  氧化锆环戊烯与异氰酸酯反应生成氮杂-或恶二唑烷环，在卤化后可方便地将其覆盖在炔烃的相应卤代酰胺化产物中。1,4-双甲基甲硅烷基取代的氧化锆环戊二烯的碘酰胺化产物收率低，而用膦稳定的锆-炔配合物则使碘酰胺化产物收率适中。另一方面，氧化锆环戊烷与异氰酸酯反应，得到异氰酸酯，异氰脲酸酯的三聚产物。
• Efficient and Selective Trimerization of Aryl and Alkyl Isocyanates Catalyzed by Sodium<i>p</i>-Toluenesulfinate in the Presence of TBAI in a Solvent-Free Condition
  作者：Firouz Matloubi Moghaddam、Mohammad G. Dekamin、Mohammad S. Khajavi、Seifollah Jalili

  DOI：10.1246/bcsj.75.851

  日期：2002.4

  Aryl and alkyl isocyanates have been efficiently converted into symmetrical trisubstituted aryl and alkyl isocyanurates, catalyzed by sodium p-toluenesulfinate on its own or in the presence of tetrabutylammonium iodide (TBAI), in a solvent-free condition. The latter has been shown to have a higher catalytic activity.

  在对甲苯磺酸钠本身或碘化四丁基铵（TBAI）的催化下，芳基和烷基异氰酸酯可在无溶剂条件下高效转化为对称的三取代芳基和烷基异氰酸酯。后者已被证明具有更高的催化活性。
• An expeditious method for the selective cyclotrimerization of isocyanates initiated by TDAE
  作者：Alain G. Giuglio-Tonolo、Cédric Spitz、Thierry Terme、Patrice Vanelle

  DOI：10.1016/j.tetlet.2014.03.045

  日期：2014.4

  We developed a rapid and green synthesis of various isocyanurates by cyclotrimerization of isocyanates using TDAE (tetrakis(dimethylamino)ethylene). TDAE displays excellent performance in catalytic quantities, affording the corresponding trimer of isocyanates very rapidly, under air and at room temperature in good to excellent yields.

  我们通过使用TDAE（四（二甲基氨基）乙烯）对异氰酸酯进行环三聚开发了各种异氰脲酸酯的快速绿色合成方法。TDAE在催化量上显示出优异的性能，在空气中和室温下以非常好的收率非常快地提供了相应的异氰酸酯三聚体。
• Fast cyclotrimerization of a wide range of isocyanates to isocyanurates over acid/base conjugates under bulk conditions
  作者：Li Wu、Wei Liu、Jinxing Ye、Ruihua Cheng

  DOI：10.1016/j.catcom.2020.106097

  日期：2020.10

  trimerization of various isocyanates. The performance depended greatly on the combination of the catalyst systems, and the [HTBD][OAc] (acetic acid) catalyst systems were considerably the most active in contrast to the corresponding DMAP and DBU counterparts. The [HTBD][OAc] catalyst system was capable of providing isocyanurates from the cyclotrimerization of various isocyanate substrates in excellent

  一系列有机碱DMAP（4-二甲基氨基吡啶），DBU（1，8-二氮杂双环[5.4.0] undec-7-ene），TBD（1，5，7-三氮杂双环[4.4.0] dec-5-ene ），并在各种异氰酸酯的三聚反应中评估了它们的碱/酸共轭有机催化剂体系。性能很大程度上取决于催化剂体系的组合，与相应的DMAP和DBU相比，[HTBD] [OAc]（乙酸）催化剂体系的活性最高。[HTBD] [OAc]催化剂体系即使在大量条件下，也能够在数秒内以优异的产率从各种异氰酸酯底物的环三聚反应中提供异氰脲酸酯。提出了在[HTBD] [OAc]上的双功能催化机理。