2-(3,5-dimethylphenylimino)pyrroline | 380635-17-6

• 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: 2-(3,5-dimethylphenylimino)pyrroline
• 英文别名: (4,5-dihydro-3H-pyrrol-2-yl)-(3,5-dimethyl-phenyl)-amine；N-(3,5-dimethylphenyl)-3,4-dihydro-2H-pyrrol-5-amine
• CAS: 380635-17-6
• 化学式: C₁₂H₁₆N₂
• mdl: MFCD02942349
• 分子量: 188.272
• InChiKey: DBJBCHMVPLIZPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 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：

  pentamethylcyclopentadienylzirconium(IV) trichloride 、 2-(3,5-dimethylphenylimino)pyrroline 在 甲基锂 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 5.0h， 以89%的产率得到[Cp*Zr(2-(N-xylylamino)pyrrolinate)Cl2]
  参考文献：
  名称：

  锆和Ha肼二三明治半三明治复合物：合成和反应性。

  摘要：

  合成了肼二胺配合物[Cp * M（N xyl N）（NNPh 2）（dmap）]（M = Zr，3a ; M = Hf，3b ; N xyl N = 2-（N -xylylamino）pyrrolinate），并且已经研究了它们的反应性。两种络合物分别由[Cp * M（N xyl N）Cl 2 ]（1a，b）和[Cp * M（N xyl N）（NHNPh 2）Cl]（2a，b）制备，作为前体。尽管在dmap存在下使用LiHMDS通过2a的脱卤化氢获得3a，但2b的反应首先用LiHMDS制备[Cp * Hf（N xyl N）（NHNPh 2）2 ]（6）和[Cp * Hf（N xyl N）（NNPh 2）LiHMDS]（4）的混合物，然后在dmap的存在会产生3b。的[Cp * Zr的（N XYL N）（NNPh 2）吡啶（DMAP）（图3a）与二异丙基反应，得到重排的[2 + 2]环加成产物的[Cp

  DOI：

  10.1021/om500087s

文献信息

• Titanium hydroamination catalysts bearing a 2-aminopyrrolinato spectator ligand: monitoring the individual reaction steps
  作者：Katharina Weitershaus、Benjamin D. Ward、Raphael Kubiak、Carsten Müller、Hubert Wadepohl、Sven Doye、Lutz H. Gade

  DOI：10.1039/b902038a

  日期：——

  ligand N(Xyl)N}(-) as the ancillary ligand, have been prepared and are shown to be pre-catalysts for the hydroamination of alkynes. The coordination of N(Xyl)N}(-) to titanium was achieved by reaction of [Cp*TiMe(3)] with the protioligand N(Xyl)NH giving [Cp*Ti(N(Xyl)N)(Me)(2)] (). Upon reaction of complex with an excess of tert-butylamine, the imido complex [Cp*Ti(N(Xyl)N)(N(t)Bu)(NH(2)(t)Bu)] () was

  制备了一系列新的钛半三明治复合物，其中含有2-氨基吡咯啉基配体N（Xyl）N}（-）作为辅助配体，并被证明是炔烃加氢胺化的预催化剂。N（Xyl）N}（-）与钛的配位反应是通过[Cp * TiMe（3）]与部分配体N（Xyl）NH反应得到[Cp * Ti（N（Xyl）N）（Me） ）（2）]（）。在配合物与过量的叔丁胺反应后，形成亚氨基配合物[Cp * Ti（N（Xyl）N）（N（t）Bu）（NH（2）（t）Bu）]（）。后者为合成一系列N-芳基取代的亚氨基络合物提供了准备。亚胺基配体与2,6-二甲基苯胺，2,4,6-三甲基苯胺以及2,6-二异丙基苯胺的交换在干净的反应中得到了相应的芳基酰亚胺络合物。钛亚氨基络合物[Cp * Ti（N（Xyl）N）（N（t）Bu）（NH（2）（t）Bu）]与末端芳基乙炔，例如苯乙炔和甲苯基乙炔的反应导致CH活化和炔基/酰胺基络合物的形成，而芳基酰亚胺基络合物又干净地进行了2
• 2-Aminopyrrolines:  New Chiral Amidinate Ligands with a Rigid Well-Defined Molecular Structure and Their Coordination to Ti^IV
  作者：Benjamin D. Ward、Hélène Risler、Katharina Weitershaus、Stéphane Bellemin-Laponnaz、Hubert Wadepohl、Lutz H. Gade

  DOI：10.1021/ic060809y

  日期：2006.9.1

  The use of an amino-oxazolinate (NNox = kappa(2)-2,6-dimethylphenylamido-4(S)-isopropyloxazoline) as a chiral analogue to amidinate ligands in the chemistry of titanium was found to lead to undesired side reactions. The reaction of 2,6-dimethylphenylamido-4(S)-isopropyloxazoline with [Ti(NMe2)(4)] afforded the bis(amidinato) complex [ Ti( NNox) 2( NMe2) 2] ( 2) which was thermally converted to the ring-opened decomposition products [Ti(NNox) kappa(3)-N( 2,6-C6H3Me2) C(NMe2)NC(Pr-i)CH2O}(NMe2)] (3) and [Ti kappa(3)-N(2,6-C6H3Me2)C(NMe2)-NC(Pr-i) CH2O}(2)] (4). The NMR spectra of 4 recorded at low temperature displayed two sets of resonances corresponding to two symmetric isomers in a 2: 5 ratio, the probable geometries of which were established by ONIOM (QM/MM) simulations. To suppress ring opening of the oxazolines, their oxygen atom was formally replaced by a CH2 group in the synthesis of a series of amino-pyrroline protioligands 2-RN(H)(5-C4H5NR') (HNRNR'). Their reaction with [ Ti( NMe2) 4] gave the thermally stable complexes [Ti((NNR')-N-R)(2)(NMe2)(2)], of which three derivatives were characterized by X-ray diffraction. They are stereochemically dynamic and undergo reversible ligand rearrangements in solution, for which the activation parameters were determined by variable-temperature H-1 NMR spectroscopy.
• Zirconium and Hafnium Hydrazinediido Half-Sandwich Complexes: Synthesis and Reactivity
  作者：Peter D. Schweizer、Hubert Wadepohl、Lutz H. Gade

  DOI：10.1021/om500087s

  日期：2014.4.14

  The hydrazinediido complexes [Cp*M(NxylN)(NNPh2)(dmap)] (M = Zr, 3a; M = Hf, 3b; NxylN = 2-(N-xylylamino)pyrrolinate) have been synthesized, and their reactivity has been investigated. Both complexes were prepared from [Cp*M(NxylN)Cl2] (1a,b) and [Cp*M(NxylN)(NHNPh2)Cl] (2a,b), respectively, as precursors. While 3a was obtained by dehydrohalogenation of 2a using LiHMDS in the presence of dmap, reaction

  合成了肼二胺配合物[Cp * M（N xyl N）（NNPh 2）（dmap）]（M = Zr，3a ; M = Hf，3b ; N xyl N = 2-（N -xylylamino）pyrrolinate），并且已经研究了它们的反应性。两种络合物分别由[Cp * M（N xyl N）Cl 2 ]（1a，b）和[Cp * M（N xyl N）（NHNPh 2）Cl]（2a，b）制备，作为前体。尽管在dmap存在下使用LiHMDS通过2a的脱卤化氢获得3a，但2b的反应首先用LiHMDS制备[Cp * Hf（N xyl N）（NHNPh 2）2 ]（6）和[Cp * Hf（N xyl N）（NNPh 2）LiHMDS]（4）的混合物，然后在dmap的存在会产生3b。的[Cp * Zr的（N XYL N）（NNPh 2）吡啶（DMAP）（图3a）与二异丙基反应，得到重排的[2 + 2]环加成产物的[Cp