1,3,5-tris(3-methylphenyl)-1,3,5-triazinane-2,4,6-trione | 62522-07-0

• 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: 1,3,5-tris(3-methylphenyl)-1,3,5-triazinane-2,4,6-trione
• 英文别名: 1,3,5-Tri-(m-Tolyl)isocyanurat；1,3,5-tris(3-methlyphenyl)-1,3,5-triazinane-2,4,6-trione；1,3,5-tris(m-tolyl)-1,3,5-triazinane-2,4,6-trione；1,3,5-tri-m-tolyl-1,3,5-triazinane-2,4,6-trione；1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-tris(3-methylphenyl)-
• CAS: 62522-07-0
• 化学式: C₂₄H₂₁N₃O₃
• 分子量: 399.449
• InChiKey: KMFOUIWYCCYNIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  异氰酸间甲苯酯 在 C₄₇H₇₉N₄Si₃Y 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以98%的产率得到1,3,5-tris(3-methylphenyl)-1,3,5-triazinane-2,4,6-trione
  参考文献：
  名称：

  硅酰胺基配体支撑的二烷基钇：异氰酸酯环三聚的合成，结构和催化† ‡

  摘要：

  合成了空间需求的硅sil（ArN = Si（L）NHAr）配体，并用于制备钇二烷基络合物，该催化剂催化了异氰酸酯的环三聚反应，具有很高的活性和出色的官能团耐受性。

  DOI：

  10.1039/c9cc06282c

文献信息

• Yttrium dialkyl supported by a silaamidinate ligand: synthesis, structure and catalysis on cyclotrimerization of isocyanates
  作者：Deshuai Liu、Dahai Zhou、Hao Yang、Jianfeng Li、Chunming Cui

  DOI：10.1039/c9cc06282c

  日期：——

  A sterically demanding silaamidine (ArN = Si(L)NHAr) ligand was synthesized and employed for the preparation of a yttrium dialkyl complex, which catalytically enabled the cyclotrimerization of isocyanate with high activity and excellent functional group tolerance.

  合成了空间需求的硅sil（ArN = Si（L）NHAr）配体，并用于制备钇二烷基络合物，该催化剂催化了异氰酸酯的环三聚反应，具有很高的活性和出色的官能团耐受性。
• Polymer-Supported, Carbon Dioxide-Protected N-Heterocyclic Carbenes: Synthesis and Application in Organo- and Organometallic Catalysis
  作者：Gajanan Manohar Pawar、Michael R. Buchmeiser

  DOI：10.1002/adsc.200900658

  日期：2010.3.22

  2‐ylmethyl)‐3‐(2‐Pr)‐3,4,5,6‐tetrahydropyrimidin‐2‐ylidine](COD) (Ir‐1) were used as homogeneous analogues and their reactivity in the above‐mentioned reactions was compared with that of the supported catalytic systems. In all reactions investigated, the TONs achieved with the supported systems were very similar to the ones obtained with the unsupported, homogeneous ones, the turn‐over frequencies

  描述了树脂支撑的，二氧化碳保护的N杂环卡宾（NHC）的合成及其在有机催化和有机金属催化中的用途。树脂结合的二氧化碳保护的NHC基催化剂是通过1,4,4a，5,8,8a-六氢-1,4,5,8- exo，endo - dimethanonaphthalene（DMNH6）的开环复分解共聚制备的）与3-（双环[2.2.1]庚-5-en-2-基甲基）-1-（2-丙基）-3,4,5,6-四氢嘧啶-1-基-2-羧酸盐（M1） ，使用定义明确的Schrock催化剂Mo [ N -2,6-（2-Pr）2 -C 6 H 3 ]（CHCMe 2 Ph）（OCMe 3）2并用于一系列有机催化反应，即，用于异氰酸酯的三聚反应，以及用于羰基化合物的氰基硅烷化。在后一反应中，周转数（TON）达到5000。此外，聚合物支撑的，二氧化碳保护的N杂环卡宾是各种聚合物支撑的金属配合物的优异祖先。它装有一系列铑（I），铱（I）
• CO₂and Sn^IIAdducts of N-Heterocyclic Carbenes as Delayed-Action Catalysts for Polyurethane Synthesis
  作者：Bhasker Bantu、Gajanan Manohar Pawar、Ulrich Decker、Klaus Wurst、Axel M. Schmidt、Michael R. Buchmeiser

  DOI：10.1002/chem.200802670

  日期：2009.3.16

  rivals: Both CO2‐protected tetrahydropyrimidin‐2‐ylidene‐based N‐heterocyclic carbenes (NHCs) and SnII‐1,3‐dimesitylimidazol‐2‐ylidene, as well as SnII‐1,3‐dimesitylimidazolin‐2‐ylidene complexes (example displayed), have been identified as truly latent catalysts for polyurethane (PUR) synthesis rivaling all existing systems both in activity and latency.

  催化竞争对手：既有CO 2保护的基于四氢嘧啶-2-亚甲基的N-杂环卡宾（NHC）和Sn II - 1,3-二苯甲酰亚胺-2-亚基，以及Sn II - 1,1,3-二甲酰亚胺二唑-2-亚烷基络合物（显示的例子）已被证实是聚氨酯（PUR）合成的真正潜在催化剂，在活性和潜伏期方面可与所有现有系统匹敌。
• Highly efficient cyclotrimerization of isocyanates using N-heterocyclic olefins under bulk conditions
  作者：Chengkai Li、Wuchao Zhao、Jianghua He、Yuetao Zhang

  DOI：10.1039/c9cc06402h

  日期：——

  of isocyanurates could be achieved from N-heterocyclic olefin mediated organocatalytic cyclotrimerization of a wide range of isocyanates under bulk conditions. Experimental details coupled with structural characterization of the key intermediates led to comprehensive mechanistic studies of cyclotrimerization.

  催化剂负载量低至0.005％时，在本体条件下，N-杂环烯烃介导的各种异氰酸酯的有机催化环三聚反应可实现高至优异的异氰脲酸酯收率。实验细节以及关键中间体的结构表征导致了对环三聚化反应的全面机理研究。
• 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。