o-diethylanilinelithium

• 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: o-diethylanilinelithium
• 英文别名: 2-diethylaminomethylphenyllithium；2-(dimethylaminoethyl)phenyllithium；[2-(Et2NCH2)C6H4]Li；[2-(Et2NCH2)CH2]Li
• 化学式: C₁₁H₁₆LiN
• 分子量: 169.196
• InChiKey: YUNSOOWQOHCNSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  o-diethylanilinelithium 在 selenium 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Group 12 metal aryl selenolates. Crystal and molecular structure of [2-(Et2NCH2)C6H4]2Se2 and [2-(Me2NCH2)C6H4Se]2M (M=Zn, Cd)

  摘要：

  Diorganodiselenide [2-(Et2NCH2)C6H4](2)Se-2 (1) was obtained by hydrolysis/oxidation of the corresponding [2-(Et2NCH2)C6H4]SeLi derivative. The treatment of [2-(Et2NCH2)C6H4](2)Se-2 with elemental sodium in THF resulted in [2-(Et2NCH2)C6H4]SeNa (2). Reactions between alkali metal selenolates [2(R2NCH2)C6H4]SeM' (R = Me, Et; M' = Li, Na) and MCl2 (M = Zn, Cd) in a 2:1 molar ratio resulted in the [2-(R2NCH2)C6H4Se](2)M species [R = Me, M = Zn (3), Cd (4); R = Et, M = Zn (5), Cd (6)]. The new compounds were characterized by multinuclear NMR (H-1, C-13, Se-77, Cd-113) and mass spectrometry. The crystal and molecular structures of 1, 3 and 4 revealed monomeric species stabilized by N -> Se (for 1) and N -> M (for 3 and 4) intramolecular interactions. (C) 2010 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.07.036
• 作为产物：
  描述：

  N‐(2‐bromobenzyl)‐N-ethylethanamine 在 正丁基锂 作用下， 以 正己烷 为溶剂， 以30.6%的产率得到o-diethylanilinelithium
  参考文献：
  名称：

  Group 12 metal aryl selenolates. Crystal and molecular structure of [2-(Et2NCH2)C6H4]2Se2 and [2-(Me2NCH2)C6H4Se]2M (M=Zn, Cd)

  摘要：

  Diorganodiselenide [2-(Et2NCH2)C6H4](2)Se-2 (1) was obtained by hydrolysis/oxidation of the corresponding [2-(Et2NCH2)C6H4]SeLi derivative. The treatment of [2-(Et2NCH2)C6H4](2)Se-2 with elemental sodium in THF resulted in [2-(Et2NCH2)C6H4]SeNa (2). Reactions between alkali metal selenolates [2(R2NCH2)C6H4]SeM' (R = Me, Et; M' = Li, Na) and MCl2 (M = Zn, Cd) in a 2:1 molar ratio resulted in the [2-(R2NCH2)C6H4Se](2)M species [R = Me, M = Zn (3), Cd (4); R = Et, M = Zn (5), Cd (6)]. The new compounds were characterized by multinuclear NMR (H-1, C-13, Se-77, Cd-113) and mass spectrometry. The crystal and molecular structures of 1, 3 and 4 revealed monomeric species stabilized by N -> Se (for 1) and N -> M (for 3 and 4) intramolecular interactions. (C) 2010 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.07.036

文献信息

• Intramolekular stickstoffstabilisierte Organoaluminiumverbindungen mit Naphthyl-, Benzyl- und Phenylliganden
  作者：Herbert Schumann、Sebastian Dechert、Markus Hummert、Katharina C. H. Lange、Stefan Schutte、Birgit C. Wassermann、Katrin Köhler、Jens Eichhorn

  DOI：10.1002/zaac.200400033

  日期：2004.8

  N-Dimethylnaphthylamin (1) reagiert mit Butyllithium zu Li(Et2O)C10H6NMe2-8 (2). Die Umsetzung von 2 mit Et2AlCl und EtAlCl2 fuhrt zu Et2AlC10H6NMe2-8 (3) bzw. EtAl(C10H6NMe2-8)2 (5) und mit iBu2AlCl wird iBu2AlC10H6NMe2-8 (4) gebildet. 1 reagiert mit Me3Al zum entsprechenden Addukt Me3AlN(C10H7)Me2 (6). LiCH2C6H4NMe2-2 (7) und LiC6H4CH2NR2-2 (R = Me (10), Et (12)) reagieren mit Me2AlCl, Et2AlCl und iBu2AlCl unter Bildung

  N, N-二甲基萘胺 (1) 与丁基锂反应生成 Li (Et2O) C10H6NMe2-8 (2)。2 与 Et2AlCl 和 EtAlCl2 反应生成 Et2AlC10H6NMe2-8 (3) 或 EtAl (C10H6NMe2-8) 2 (5) 并与 iBu2AlCl iBu2AlC10H6NMe2-8 (4) 形成。1 与 Me3Al 反应生成相应的加合物 Me3AlN (C10H7) Me2 (6)。LiCH2C6H4NMe2-2 (7) 和 LiC6H4CH2NR2-2 (R = Me (10)、Et (12)) 与 Me2AlCl、Et2AlCl 和 iBu2AlCl 反应生成 R2AlCH2C6H4NMe2-2 (R = Me (8)、Et (9))、iBu2AlCl -2 (11) 和 Et2AlC6H4CH2NEt2-2 (13)。新化合物通过元素分析、1H、13C 和 27Al-NMR
• Dynamic NMR as a Nondestructive Method for the Determination of Rates of Dissociation. IX. Rates of Dissociative Reactions of the Coordinated Form of [<i>o</i>-(Diethylaminomethyl)phenyl]halodimethyl(or diphenyl)stannanes
  作者：Michinori Oki、Manabu Ohira

  DOI：10.1246/bcsj.57.3117

  日期：1984.11

  spectra. Examination of a series of halogen compounds by total line shape analysis of the diastereotopic methylene proton signals revealed that, at 10 °C, the rates of dissociation were 11.7, 22.9, 28.6, and 73.3 s−1 for fluoro, chloro, bromo, and iodo compounds, respectively: The results are in conformity with the expectation from the electronegativity of halogens. The relatively small differences in

  发现 [o-(二乙基氨基甲基) 苯基] 卤代二甲基 (或二苯基) 锡烷的配位形式在其 1 H NMR 光谱中表现出动态行为。通过非对映异构亚甲基质子信号的总线形分析检查一系列卤素化合物表明，在 10 °C 下，氟、氯、溴和溴的解离速率分别为 11.7、22.9、28.6 和 73.3 s-1。碘化合物，分别为：该结果与从卤素的电负性的期望相一致。整个系列中活化参数的相对较小差异可能包括溶剂化能的贡献。二苯基化合物相对于相应的二甲基化合物表现出快速的交换率。这归因于空间因子而不是 pπ-dπ 相互作用。
• The lithiation of arylamines and the preparation of cyclopentadienyltitanium(IV) arylaminate complexes
  作者：Anthony G Avent、Peter B Hitchcock、G.Jeffery Leigh、Maria Togrou

  DOI：10.1016/s0022-328x(02)02222-2

  日期：2003.3

  The 2-lithio-derivatives of a range of aryl-substituted amines were prepared, generally from the 2-bromo-compounds and butyllithium. These compounds cause dinitrogen uptake when mixed with [VCl2(Me2NCH2CH2NMe2)2] though no dinitrogen complexes were characterised. With [TiCpCl3] the lithio-derivatives form compounds [TiCpCl2(arylaminate)] the NMR spectra of which were studied in some detail. The X-ray

  通常由2-溴化合物和丁基锂制备一系列芳基取代的胺的2-硫代衍生物。这些化合物与[VCl 2（Me 2 NCH 2 CH 2 NMe 2）2 ]混合时会引起二氮吸收，尽管未鉴定出二氮配合物。用[TiCpCl 3 ]的硫代衍生物形成的化合物[TiCpCl 2（芳基化物）]进行了详细的NMR光谱研究。[LIC的X射线结构6 ħ 4 -2-CH 2 N（CH 2 CHCH 2）2 } 4]和[合成TiCp（C 6 H ^ 4 CH 2 R）氯2 ]（R = NME 2，N（CH 2 CHCH 2）2或NC 4 H ^ 8 O）中描述。
• Novel rhodate and iridate complexes containing C,N chelating arylamine ligand systems
  作者：Ingrid C.M. Wehman-Ooyevaar、Joseph A. Vedral、Johann T.B.H. Jastrzebski、David M. Grove、Gerard van Koten

  DOI：10.1016/0022-328x(93)83026-r

  日期：1993.6

  effect of the bulky organic group on the N-donor atom. All the -ate complexes are formed diastereoselectively (and in the case of C6H4CH(Me)NMe2-(R)-2, enantioselectively). 1H and 13C NMR spectroscopies show the -ate complexes to be monomeric, heterobimetallic species. The 13C NMR data show clearly that Cipso is bridging between the late transition metal and the lithium centre. Consequently, this Cipso

  该合成了一系列新的iridate和rhodate络合物李（L-的描述Ç，Ñ）2（; COD =环辛-1,5-二烯M =铑，铱）含有M（COD）邻-chelating，单-anionic，芳基胺配位体L = C 6 H ^ 4 CH 2 NR 2 -2（R =甲基，乙基），C 6 H ^ 3 CH 2 NME 2 - 2-ME-5，C 6 H ^ 4 CH（Me）的NME 2 -（R）-2或C 6 H 4 CH 2 NMe（tBu）-2。[MCl（cod）] 2的-ate配合物的合成方法取决于起始芳基锂化合物在苯中的溶解度，这是庞大的有机基团对N-给体原子的间接影响。所有的-ate络合物都是非对映选择性地形成的（在C 6 H 4 CH（Me）NMe 2-（R）-2的情况下，是对映选择性的）。1 H和13 C NMR光谱表明-ate配合物是单体的异双金属物种。的13个C NMR数据清楚地表明，
• Homoleptic Organometallic Compounds of Zinc, Cadmium, and Mercury, Intramolecularly Stabilized by Amine Ligands
  作者：Herbert Schumann、Silke Freitag、Frank Girgsdies、Holger Hemling、Gabriele Kociok-Köhn

  DOI：10.1002/(sici)1099-0682(199802)1998:2<245::aid-ejic245>3.0.co;2-t

  日期：1998.2

  Homoleptic intramolecularly stabilized organozinc, -cadmium, and -mercury compounds MR2, with R bearing an amino function, have been synthesized from the corresponding metal dichlorides MCl2 and the lithium salts LiC6H4CH2NEt2-2 (1), LiC6H3(CH2NMe2)2-2,6 (2), LiC6H3(CH2NEt2)2-2,6 (3), (LiCH2CH2CH2)2NMe (4), and LiCH2CH2CH2NC5H10 (5). The crystal structures of Hg(C6H4CH2NEt2-2)2 (1c), [M(CH2CH2CH2)2NMe]2

  由相应的金属二氯化物 MCl2 和锂盐 LiC6H4CH2NEt2-2 (1)、LiC6H3(CH2NMe2)2-2,6 合成了均质分子内稳定的有机锌、镉和汞化合物 MR2，其中 R 带有氨基功能(2)、LiC6H3(CH2NEt2)2-2,6 (3)、(LiCH2CH2CH2)2NMe (4) 和 LiCH2CH2CH2NC5H10 (5)。Hg(C6H4CH2NEt2-2)2 (1c), [M(CH2CH2CH2)2NMe]2 [M = Zn (4a), Hg (4c)] 和 M(CH2CH2CH2NC5H10)2 [M = Zn (5a) 的晶体结构), Cd (5b)] 已通过 X 射线衍射测定。图 4a 和 4c 形成具有不寻常配位数（三）的中心金属的二聚体。