N-(2,6-Diisopropyl-phenyl)-N'-(2,4,6-trimethyl-phenyl)-ethane-1,2-diamine | 920337-56-0

• 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-(2,6-Diisopropyl-phenyl)-N'-(2,4,6-trimethyl-phenyl)-ethane-1,2-diamine
• 英文别名: N'-[2,6-di(propan-2-yl)phenyl]-N-(2,4,6-trimethylphenyl)ethane-1,2-diamine
• CAS: 920337-56-0
• 化学式: C₂₃H₃₄N₂
• 分子量: 338.536
• InChiKey: CHIDLOLGNOLXFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.38
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  24.06
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(2,6-Diisopropyl-phenyl)-N'-(2,4,6-trimethyl-phenyl)-ethane-1,2-diamine 、 原甲酸三乙酯 在 盐酸 作用下， 反应 2.0h， 以1.26 g的产率得到1-(2,6-二-异丙基苯基)-3-(2,4,6-三甲基苯基)-4,5-二氢咪唑氯化物
  参考文献：
  名称：

  Room-Temperature Negishi Cross-Coupling of Unactivated Alkyl Bromides with Alkyl Organozinc Reagents Utilizing a Pd/N-Heterocyclic Carbene Catalyst

  摘要：

  A high-yielding cross-coupling reaction of unactivated alkyl bromides possessing beta-hydrogens with alkylzinc halides utilizing a Pd/N-heterocyclic carbene (NHC) catalyst at room temperature is described. A variety of Pd sources, Pd-2(dba)(3), Pd(OAc)(2), or PdBr2, with the commercially available ligand precursor 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPr center dot HCl) successfully coupled 1-bromo-3-phenylpropane with n-butylzinc bromide in THF/NMP. An investigation of different NHC precursors showed that the bulky 2,6-diisopropylphenyl moiety was necessary to achieve high coupling yields (75-85%). The corresponding ethyl analogue was moderately active (11%). A range of unsymmetrical NHC precursors were prepared and evaluated. The ligand precursor containing one 2,6-diisopropylphenyl and one 2,6-diethylphenyl afforded the coupling product in 47% yield, clearly suggesting a direct relationship between the steric topography created by the flanking N-substituents and catalyst activity. Under optimal conditions, a number of alkyl bromides and alkylzinc halides possessing common functional groups (amide, nitrile, ester, acetal, and alkyne) were effectively coupled (61-92%). It is noteworthy that beta-substituted alkyl bromides and alkylzinc halides successfully underwent cross-coupling. Also, under these conditions alkyl chlorides were unaffected.

  DOI：

  10.1021/jo051304c
• 作为产物：
  描述：

  2-((2,6-diisopropylphenyl)amino)-2-oxoacetic acid 在 硼烷四氢呋喃络合物 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 40.0h， 生成 N-(2,6-Diisopropyl-phenyl)-N'-(2,4,6-trimethyl-phenyl)-ethane-1,2-diamine
  参考文献：
  名称：

  Room-Temperature Negishi Cross-Coupling of Unactivated Alkyl Bromides with Alkyl Organozinc Reagents Utilizing a Pd/N-Heterocyclic Carbene Catalyst

  摘要：

  A high-yielding cross-coupling reaction of unactivated alkyl bromides possessing beta-hydrogens with alkylzinc halides utilizing a Pd/N-heterocyclic carbene (NHC) catalyst at room temperature is described. A variety of Pd sources, Pd-2(dba)(3), Pd(OAc)(2), or PdBr2, with the commercially available ligand precursor 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPr center dot HCl) successfully coupled 1-bromo-3-phenylpropane with n-butylzinc bromide in THF/NMP. An investigation of different NHC precursors showed that the bulky 2,6-diisopropylphenyl moiety was necessary to achieve high coupling yields (75-85%). The corresponding ethyl analogue was moderately active (11%). A range of unsymmetrical NHC precursors were prepared and evaluated. The ligand precursor containing one 2,6-diisopropylphenyl and one 2,6-diethylphenyl afforded the coupling product in 47% yield, clearly suggesting a direct relationship between the steric topography created by the flanking N-substituents and catalyst activity. Under optimal conditions, a number of alkyl bromides and alkylzinc halides possessing common functional groups (amide, nitrile, ester, acetal, and alkyne) were effectively coupled (61-92%). It is noteworthy that beta-substituted alkyl bromides and alkylzinc halides successfully underwent cross-coupling. Also, under these conditions alkyl chlorides were unaffected.

  DOI：

  10.1021/jo051304c

文献信息

• Ruthenium Metallacycles Derived from 14-Electron Complexes. New Insights into Olefin Metathesis Intermediates
  作者：Anna G. Wenzel、Robert H. Grubbs

  DOI：10.1021/ja0666598

  日期：2006.12.1

  Ruthenium(IV) metallacycles derived from both ethylene and propene are reported. The propene-derived metallacycles represent the first observed examples of substituted ruthenacyclobutanes and offer new insight into the preferred stereochemical orientation about metathesis intermediates. In addition, a metallacycle possessing an unsymmetrical N-heterocyclic carbene (NHC) ligand was prepared and investigated

  报道了衍生自乙烯和丙烯的钌 (IV) 金属环。丙烯衍生的金属环代表了第一个观察到的取代钌环丁烷的例子，并提供了关于复分解中间体的首选立体化学取向的新见解。此外，制备并研究了具有不对称 N-杂环卡宾 (NHC) 配体的金属环，以确定 NHC 相对于金属环的动力学。发现所研究的金属环在 2D NMR 中的 alpha 和 beta 位置之间具有交换交叉峰，表明具有动态结构。讨论了这些结果对钌催化烯烃复分解机理的影响。