1,3-dimesityl-3,4,5,6-tetrahydropyrimidin-1-ium-2-carboxylate | 1159203-60-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,3-dimesityl-3,4,5,6-tetrahydropyrimidin-1-ium-2-carboxylate
• 英文别名: 1,3-bis(2,4,6-trimethylphenyl)-5,6-dihydro-4H-pyrimidin-1-ium-2-carboxylate
• CAS: 1159203-60-7
• 化学式: C₂₃H₂₈N₂O₂
• 分子量: 364.488
• InChiKey: PDLWXADHILMNDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  46.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-dimesityl-3,4,5,6-tetrahydropyrimidin-1-ium-2-carboxylate 、 copper(l) chloride 以 甲苯 为溶剂， 以95%的产率得到CuCl(1,3-dimesityl-3,4,5,6-tetrahydropyrimidin-2-ylidene)
  参考文献：
  名称：

  用于胶束条件下的点击化学和氢化硅烷化反应的开环易位聚合反应衍生的，聚合物结合的铜催化剂。

  摘要：

  开环易位聚合已用于由亲水单体5- {2- [2-（2-甲氧基-乙氧基）合成两亲嵌段共聚物聚（M1-co-M3）-b-聚（M2） ）-乙氧基]-乙氧基甲基} -7-氧杂双环[2.2.1]庚-2-烯（M2）和疏水性单体endo，exo-5-癸氧基甲基-双环[2.2.1]庚-2-烯（M1） ）和1,3-二（1-间甲苯基）-4-{[（（双环[2.2.1]庚-5-烯-2-基羰基）氧基]甲基} -4,5-二氢ro-1H-咪唑-羧酸3-铵（M3）。聚（M1-co-M3）-b-聚（M2）负载有Cu，所得的负载有Cu（I）的聚合物poly（M1-co-M3）-b-poly（M2）-Cu用于制备胶束条件下的一系列铜催化反应，即叠氮化物[3 + 2]环加成至炔烃和羰基氢化硅烷化反应。在这种胶束状态下 发现与聚合物结合的铜催化剂是所有研究反应的有效催化剂。环加成反应中的周转数（TONs）在200-375的范围内，

  DOI：

  10.1039/b909180g
• 作为产物：
  描述：

  N,N'-dimesitylformamidine 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 生成 1,3-dimesityl-3,4,5,6-tetrahydropyrimidin-1-ium-2-carboxylate
  参考文献：
  名称：

  Anionic Ring-Opening Homo- and Copolymerization of Lactams by Latent, Protected N-Heterocyclic Carbenes for the Preparation of PA 12 and PA 6/12

  摘要：

  Laurolactam (LL) is polymerized in the bulk using strongly basic N-heterocyclic carbenes (NHCs) as initiators at temperatures of 180-200 degrees C to prepare the corresponding polyamide (PA 12). In-situ rheology of the polymerization progress reveals that an anionic mechanism is active, which is supported by the strong dependence of initiator activity on the basicity of the NHCs. GPC data and kinetic investigations show the process to be moderately controlled and fast, allowing high or quantitative yields in short polymerization times. Fifteen different NHC-CO2-adducts and NHC-metal complexes were used as thermally labile but room temperature stable NHC-precursors. Depending on the ring size and N-substituent, some of these protected NHCs allow forming a mixture of monomer and NHC-precursor that is suitable for long-term storage and readily polymerizable by simple heating. All polymerizations are executed without activator or other additives and thus represent a true one-component system for the production of PA 12. Finally, LL is copolymerized with epsilon-caprolactam (epsilon-CLA). It is found that a copolymer with a considerable gradient is formed, with epsilon-CLA being incorporated preferentially at the onset of the polymerization.

  DOI：

  10.1021/ma4018586

文献信息

• 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。
• CO ₂ , Magnesium, Aluminum, and Zinc Adducts of N‐Heterocyclic Carbenes as (Latent) Catalysts for Polyurethane Synthesis
  作者：Bhasker Bantu、Gajanan Manohar Pawar、Klaus Wurst、Ulrich Decker、Axel M. Schmidt、Michael R. Buchmeiser

  DOI：10.1002/ejic.200801161

  日期：2009.5

  (poly)urethane (PUR) synthesis. Out of nine different compounds, the dimeric complex [Zn(CH3COO)2(1,3-dimesitylimidazol-2-ylidene)]2 (7) proved to be the most active one, rivaling the industrially most relevant catalyst dibutyltin dilaurate in terms of catalytic activity. Even more important, the Mg- and Zn-derived NHC complexes as well as the CO2-protected imidazol-2-ylidenes displayed pronounced latent behavior

  制备了一系列咪唑-2-亚基-、咪唑啉-2-亚基-和四氢嘧啶-2-亚基-衍生的N-杂环卡宾(NHC)的镁、铝和锌配合物。此外，还制备了对称和非对称 CO2 保护的 imidazol-2-ylidenes 和 imidazolin-2-ylidenes。报告了选定的单晶 X 射线结构。研究了所有化合物在（聚）氨基甲酸酯（PUR）合成中的催化行为。在九种不同的化合物中，二聚复合物 [Zn(CH3COO)2(1,3-dimesitylimidazol-2-ylidene)]2 (7) 被证明是最活跃的一种，与工业上最相关的催化剂二月桂酸二丁基锡相媲美催化活性。更重要的是，Mg 和 Zn 衍生的 NHC 配合物以及 CO2 保护的咪唑-2-亚基在选定的情况下显示出明显的潜在行为和高催化活性，可与工业相关的潜在催化剂新癸酸苯汞相媲美并超过其。这允许创建具有显着适用期的单组分 PUR 系统。对于所有基于镁和锌的
• [DE] KATALYSATOREN ZUR SYNTHESE VON POLYURETHANEN<br/>[EN] CATALYSTS FOR THE SYNTHESIS OF POLYURETHANES<br/>[FR] CATALYSEURS POUR LA SYNTHÈSE DE POLYURÉTHANES
  申请人：BAYER MATERIALSCIENCE AG

  公开号：WO2009135600A1

  公开（公告）日：2009-11-12

  Es werden neue Katalysatoren zur Synthese von Polyurethanen beschrieben, die den allgemeinen Formeln (I) oder (II) entsprechen oder Verbindungen, die durch die Reaktion eines Metallsalzes der Metalle Magnesium Kalzium, Yttrium, Lanthan, Titan, Zirkonium, Mangan, Eisen, Kobalt, Zink, Aluminium, Zinn, mit einem Anion der Reihe Fluorid, Chlorid, Bromid, Sulfonat, Trifluormethansulfonat, Methansulfonat, Benzolsulfonat, para-Toluolsulfonat, Carboxy-C1-C10-alkyl, Carboxy-C3-C10-cycloalkyl, Carboxy- C2-C10-alkenyl, C1-C10-alkoxy, Acetylacetonat, Trifluoracetlyacetonat oder Hexafluor- acetylacetonat, mit N-heterocyclischen Verbindungen der allgemeinen Struktur I; oder mit N-heterocyclischen Verbindungen der allgemeinen Struktur II; oder mit N-heterocyclischen Verbindungen der allgemeinen Struktur III, erhalten werden.
• Anionic Ring-Opening Homo- and Copolymerization of Lactams by Latent, Protected N-Heterocyclic Carbenes for the Preparation of PA 12 and PA 6/12
  作者：Stefan Naumann、Friedrich Georg Schmidt、Maria Speiser、Margit Böhl、Stefan Epple、Christian Bonten、Michael R. Buchmeiser

  DOI：10.1021/ma4018586

  日期：2013.11.12

  Laurolactam (LL) is polymerized in the bulk using strongly basic N-heterocyclic carbenes (NHCs) as initiators at temperatures of 180-200 degrees C to prepare the corresponding polyamide (PA 12). In-situ rheology of the polymerization progress reveals that an anionic mechanism is active, which is supported by the strong dependence of initiator activity on the basicity of the NHCs. GPC data and kinetic investigations show the process to be moderately controlled and fast, allowing high or quantitative yields in short polymerization times. Fifteen different NHC-CO2-adducts and NHC-metal complexes were used as thermally labile but room temperature stable NHC-precursors. Depending on the ring size and N-substituent, some of these protected NHCs allow forming a mixture of monomer and NHC-precursor that is suitable for long-term storage and readily polymerizable by simple heating. All polymerizations are executed without activator or other additives and thus represent a true one-component system for the production of PA 12. Finally, LL is copolymerized with epsilon-caprolactam (epsilon-CLA). It is found that a copolymer with a considerable gradient is formed, with epsilon-CLA being incorporated preferentially at the onset of the polymerization.
• Ring-opening metathesis polymerization-derived, polymer-bound Cu-catalysts for click-chemistry and hydrosilylation reactions under micellar conditions
  作者：Gajanan M. Pawar、Bhasker Bantu、Jochen Weckesser、Siegfried Blechert、Klaus Wurst、Michael R. Buchmeiser

  DOI：10.1039/b909180g

  日期：——

  Ring-opening metathesis polymerization has been used for the synthesis of the amphiphilic block-copolymer poly(M1-co-M3)-b-poly(M2) from the hydrophilic monomer 5-2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxymethyl}-7-oxabicyclo[2.2.1]hept-2-ene (M2), and the hydrophobic monomers endo,exo-5-decyloxymethyl-bicyclo[2.2.1]hept-2-ene (M1) and 1,3-di(1-mesityl)-4-[(bicyclo[2.2.1]hept-5-en-2-ylcarbonyl)oxy]methyl}-4

  开环易位聚合已用于由亲水单体5- 2- [2-（2-甲氧基-乙氧基）合成两亲嵌段共聚物聚（M1-co-M3）-b-聚（M2） ）-乙氧基]-乙氧基甲基} -7-氧杂双环[2.2.1]庚-2-烯（M2）和疏水性单体endo，exo-5-癸氧基甲基-双环[2.2.1]庚-2-烯（M1） ）和1,3-二（1-间甲苯基）-4-[（（双环[2.2.1]庚-5-烯-2-基羰基）氧基]甲基} -4,5-二氢ro-1H-咪唑-羧酸3-铵（M3）。聚（M1-co-M3）-b-聚（M2）负载有Cu，所得的负载有Cu（I）的聚合物poly（M1-co-M3）-b-poly（M2）-Cu用于制备胶束条件下的一系列铜催化反应，即叠氮化物[3 + 2]环加成至炔烃和羰基氢化硅烷化反应。在这种胶束状态下 发现与聚合物结合的铜催化剂是所有研究反应的有效催化剂。环加成反应中的周转数（TONs）在200-375的范围内，