tert-butyl 2-(diallylcarbamoyl)-pyrrolidine-1-carboxylate | 1374037-37-2

• 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: tert-butyl 2-(diallylcarbamoyl)-pyrrolidine-1-carboxylate
• 英文别名: Tert-butyl 2-[bis(prop-2-enyl)carbamoyl]pyrrolidine-1-carboxylate
• CAS: 1374037-37-2
• 化学式: C₁₆H₂₆N₂O₃
• 分子量: 294.394
• InChiKey: BEQGCQXYBBPIGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(diallylcarbamoyl)-pyrrolidine-1-carboxylate 在 1,3-bis-(2,4,6-trimethylphenyl)-2-(imidazolidinylidene)dichloro(5-nitro-2-isopropoxyphenylmethylene)ruthenium 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成 2-(2,5-dihydropyrrole-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  An attempt to provide an environmentally friendly solvent selection guide for olefin metathesis

  摘要：

  一系列环境友好型溶剂被评估应用于烯烃复分解反应中。采用了不同市售且广泛应用的钌催化剂。所得数据可作为指南，促进以更绿色的反应介质替代对环境有害的氯化或芳香族溶剂，从而使烯烃复分解技术在工业和学术领域的应用更加环保、可持续。

  DOI：

  10.1039/c3gc41943f

文献信息

• Hoveyda–Grubbs-Type Precatalysts with Unsymmetrical<i>N</i>-Heterocyclic Carbenes as Effective Catalysts in Olefin Metathesis
  作者：Paweł Małecki、Katarzyna Gajda、Osman Ablialimov、Maura Malińska、Roman Gajda、Krzysztof Woźniak、Anna Kajetanowicz、Karol Grela

  DOI：10.1021/acs.organomet.7b00211

  日期：2017.6.12

  In our search for more-selective olefin metathesis catalysts, a series of Hoveyda–Grubbs-type second-generation complexes bearing unsymmetrical N-heterocyclic carbene (NHC) ligands were synthesized and tested in model reactions. It was found that the N-benzyl substituent in NHC has a positive influence on the selectivity of the newly obtained catalysts in the self-metathesis reaction of α-olefins.

  在我们寻找更具选择性的烯烃复分解催化剂的过程中，合成了一系列带有不对称N-杂环卡宾（NHC）配体的Hoveyda-Grubbs型第二代配合物，并在模型反应中进行了测试。发现NHC中的N-苄基取代基对新获得的催化剂在α-烯烃的自我复分解反应中的选择性具有积极影响。如所预期的，观察到活性和选择性之间相对于所使用的N-芳基取代基的典型关系。含Dipp的复合物在高温下表现出更高的稳定性，而含Mes的复合物通常比其Dipp类似物具有更高的收率。
• Ruthenium Amide Complexes – Synthesis and Catalytic Activity in Olefin Metathesis and in Ring‐Opening Polymerisation
  作者：Anna Gawin、Eva Pump、Christian Slugovc、Anna Kajetanowicz、Karol Grela

  DOI：10.1002/ejic.201800251

  日期：2018.4.30

  set of olefin metathesis catalysts bearing a ruthenium amide moiety was synthesised. In the ruthenium amide form these complexes exhibit very low activity in standard metathesis reactions. However, a dramatic increase of activity was observed upon in situ activation with trimethylsilyl chloride or HCl, allowing successful application of such catalysts in a number of model ring‐closing metathesis, cross‐metathesis

  合成了一组带有钌酰胺部分的烯烃复分解催化剂。这些钌配合物在标准复分解反应中表现出非常低的活性。但是，在用三甲基甲硅烷基氯或HCl原位活化后观察到活性急剧增加，从而使这种催化剂成功应用于许多模型的闭环复分解，交叉复分解和烯炔转化。而且，这种活化的络合物被证明是用于二环戊二烯（DCPD）的本体聚合的非常有效的催化剂。研究了温度和添加剂性质等因素对聚-DCPD性能的影响。
• Efficient, durable and reusable olefin metathesis catalysts with high affinity to silica gel
  作者：Krzysztof Skowerski、Piotr Kasprzycki、Michał Bieniek、Tomasz K. Olszewski

  DOI：10.1016/j.tet.2013.06.056

  日期：2013.9

  The new Scorpio type olefin metathesis catalysts with very high affinity to silica gel are reported. After completion of the reaction, those complexes can be efficiently separated from reaction product by direct filtration of reaction mixture through a short pad of silica gel. Products obtained by this methodology are contaminated with low amounts of residual ruthenium. Especially, catalyst (H2IPr)(Cl)(2)Ru=C(H)(C6H4OR) (5b, R=CH(Me)(C(O)N(Me)OMe) exhibited very high activity and could be easily recovered and reused. Additionally, this catalyst was found to be effective already at 0.1-0.5 mol % and showed good compatibility with environmentally benign solvents. (C) 2013 Elsevier Ltd. All rights reserved.