N,N'-bis(2-tert-butylphenyl)formamidine | 1025068-41-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N'-bis(2-tert-butylphenyl)formamidine
• 英文别名: N'-(2-tert-butylphenyl)-N-(2-tert-butylphenyl)formamidine；N,N'-bis(2-tert-butylphenyl)formamidine；N,N'-bis(2-tert-butylphenyl)methanimidamide
• CAS: 1025068-41-0
• 化学式: C₂₁H₂₈N₂
• 分子量: 308.467
• InChiKey: ZQZFWBGENJWJBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N'-bis(2-tert-butylphenyl)formamidine 、 1,2-二氯乙烷 在 N,N-二异丙基乙胺 作用下， 反应 168.0h， 以91%的产率得到1,3-bis(2-tert-butylphenyl)-imidazolinium chloride
  参考文献：
  名称：

  [EN] PREPARATION OF SATURATED IMIDAZOLINIUM SALTS AND RELATED COMPOUNDS
  [FR] PRÉPARATION DE SELS D'IMIDAZOLINIUM SATURÉS ET COMPOSÉS ASSOCIÉS

  摘要：

  公开了用于制备饱和咪唑啉盐和相关化合物的方法，包括将甲酰胺与二硫乙烷等化合物发生反应以及可选的碱。另外，咪唑盐和相关化合物也可以在一步过程中制备，无需纯化甲酰胺反应物。这些方法使得在无溶剂反应条件下且产率极高的情况下获得大量咪唑啉盐和相关化合物成为可能。

  公开号：

  WO2009062171A1
• 作为产物：
  描述：

  2-叔丁基苯胺 、 原甲酸三乙酯 以38%的产率得到N,N'-bis(2-tert-butylphenyl)formamidine
  参考文献：
  名称：

  N，Nʹ-二芳基甲am：溶液中的固态结构分析和立体诱导的立体化学交换

  摘要：

  四个取代的N，N′-二芳基甲am的X射线晶体结构表明，环状的二聚体是由两个甲am以固态形式形成的，是由两个氢键促进的s-反式构型的互变异构对。在各种氘代溶剂中进行的NMR研究以及随后的酸加成表明，在邻位引入空间要求的取代基似乎使溶液中的甲am二聚体形成不稳定，导致质子信号出现，表明稀有的S-顺式异构体。当分子在取代基上具有明显的空间位阻时，s-反式异构体与s-cis共存CDCl 3，C 6 D 6和DMSO-d 6中的异构体。溶液中异构体的分布取决于溶剂的选择，浓度以及烷基取代基的体积。酸或配位溶剂的添加稳定了s-反式异构体。

  DOI：

  10.1016/j.tet.2021.131995

文献信息

• Multicomponent Synthesis of 1-Aryl 1,2,4-Triazoles
  作者：Annie Tam、Ian S. Armstrong、Thomas E. La Cruz

  DOI：10.1021/ol401428x

  日期：2013.7.19

  A multicomponent (single reactor) process for the synthesis of 1-aryl 1,2,4-triazoles was explored and developed. This transformation prepared the 1,2,4-triazole directly from anilines, amino pyridines, and pyrimidines. The reaction scope was explored with 21 different substrates, and the position of the nitrogen atoms in the newly formed ring was established by 15N labeling and NMR spectroscopy.

  探索和开发了一种用于合成1-芳基1,2,4-三唑的多组分（单反应器）工艺。该转化直接从苯胺，氨基吡啶和嘧啶制备1,2,4-三唑。用21种不同的底物探索了反应范围，并通过15 N标记和NMR光谱确定了新形成的环中氮原子的位置。
• A Modular Synthesis of Highly Substituted Imidazolium Salts
  作者：Keiichi Hirano、Slawomir Urban、Congyang Wang、Frank Glorius

  DOI：10.1021/ol8029609

  日期：2009.2.19

  A versatile and modular one-pot method for the preparation of differently substituted symmetrical and unsymmetrical imidazolium salts is reported, and 19 examples are given. In the key step, readily available formamidines and α-halo ketones are coupled to give imidazolinium salts 3, followed by imidazolium salt formation by acylation-induced elimination. For many substitution patterns of the imidazolium

  报道了一种通用且模块化的一锅法，用于制备不同取代的对称和不对称咪唑鎓盐，并给出了19个实例。在关键步骤中，将容易获得的甲am和α-卤代酮偶联，得到咪唑啉鎓盐3，然后通过酰化诱导的消除作用形成咪唑鎓盐。对于咪唑鎓盐产品的许多取代方式，在收率，合成简便性和耐用性方面，这种有效策略与众所周知的方法相比是有利的。
• An Efficient Synthesis of Imidazolinium Salts Using Vinyl Sulfonium Salts
  作者：Eoghan M. McGarrigle、Sven P. Fritz、Ludovic Favereau、Muhammad Yar、Varinder K. Aggarwal

  DOI：10.1021/ol2009472

  日期：2011.6.17

  The synthesis of imidazolinium salts from the reaction of formamidines and (2-bromoethyl)diphenylsulfonium triflate is described. A variety of symmetrical and unsymmetrical imidazolinium Inflate salts were synthesized in high yield in short reaction times under mild conditions. Aromatic and aliphatic N-substituents work well. The reaction is proposed to proceed via generation of a vinyl sulfonium salt Intermediate frorr the bromoethylsulfonium triflate.
• A Facile Preparation of Imidazolinium Chlorides
  作者：Kevin M. Kuhn、Robert H. Grubbs

  DOI：10.1021/ol800628a

  日期：2008.5.1

  A process for the preparation of symmetric and unsymmetric imidazolinium chlorides that involves reaction of a formamidine with dichloroethane and a base (a) is described. This method makes it possible to obtain numerous imidazolinium chlorides under solvent-free reaction conditions and in excellent yields with purification by simple filtration. Alternatively, symmetric imidazolinium chlorides can be prepared directly in moderate yields from substituted anilines by utilizing half of the formamidine intermediate as sacrificial base (b).
• Synthesis and structural analysis of formamidinate-supported Mg complexes
  作者：Yi-Ju Tsai、Michael B. Pastor、Wenfeng Lo、Qinliang Zhao

  DOI：10.1016/j.ica.2015.05.005

  日期：2015.8

  Reactions of 2-mesitylmagnesium bromide with N,N'-diarylformamidines afforded five Mg compounds [(DPhF)Mg(THF)(2)](2)(mu-Br)(2) (1), [D(3,5-Xyl)F](2)Mg(THF)(2) (2), [D(2,6-Xyl)F](2)Mg(THF) (3), [D(2-(PrPh)-Pr-i)F]MgBr(THF)(3) (4), and [D(2-(BuPh)-Bu-t)F](2)Mg(THF) (5). Complexes 1, 2 and 4 displayed monomeric octahedral metal centers supported by formamidinates, bromide counter anions, and coordinating THF solvent molecules, while the metal cores in 3 and 5 were five-coordinated and in distorted square-pyramidal geometries. Detailed structural analysis indicated that only dimagnesium or mononuclear complexes were obtained through the use of formamidinate ligands. Ligands of increased steric demands resulted in the formation of monomeric complexes. Solvent molecules and counter anions that can coordinate to the metal cores further regulated the product conformation. Monoanionic formamidinates in the complexes, mostly featuring two nearly identical N-C bonds on the N-C-N backbone upon complexation, exhibited a symmetric bidentate chelating (eta(2)) coordination mode. (C) 2015 Elsevier B.V. All rights reserved.