lithium N-<2-(dimethylamino)ethyl>amide | 132608-39-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: lithium N-<2-(dimethylamino)ethyl>amide
• 英文别名: lithium (2-(dimethylamino)ethyl)amide；lithium [2-(dimethylamino)ethyl]amide；N-lithio-2-(dimethylamino)ethylamide；lithium 2-(dimethylamino)ethylamide；lithium;2-(dimethylamino)ethylazanide
• CAS: 132608-39-0
• 化学式: C₄H₁₁LiN₂
• 分子量: 94.0857
• InChiKey: ZDSIFYTXXXLRGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  4.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  lithium N-<2-(dimethylamino)ethyl>amide 、 (E)-N-<(1R)-bornan-2-ylidene>-2-(trifluoromethyl)aniline 以59%的产率得到(4R)-N-<2-(dimethylamino)ethyl>-4-methyl-1,2,3,4-tetrahydro-1,4-(dimethylmethano)acridin-9-amine
  参考文献：
  名称：

  Further studies on the cyclization of aromatic azomethines ortho-substituted with a trifluoromethyl group: synthesis of 2,4-di- or 2,3,4-trisubstituted quinolines

  摘要：

  The scope and limitations of the novel synthetic route to quinolines (Strekowski et al. J. Org. Chem. 1990, 55, 4777) have been studied. A direct condensation of 2-(trifluoromethyl)aniline (1) with methyl aryl ketones, methyl heteroaryl ketones, ethyl aryl ketones, methyl vinyl ketones, 1-indanone, 1-tetralone, camphor, and cyclohexanone provides an easy access to the corresponding ketimines. An indirect one-pot preparation of dialkyl ketimines and C-alkyl-substituted amidines derived from 1, but inaccessible by the direct condensation method, is also presented. All these ketimines and amidines are cyclized in the presence of alkylamide, dialkylamide, or alkoxide bases to give a quinoline containing the base function at C-4. Analysis of byproducts of the base-mediated reactions provides strong support for the originally proposed mechanism of the quinoline formation.

  DOI：

  10.1021/jo00027a037

文献信息

• Amination by lithium alkylamide reagents of ketimines derived from 2-(trifluoromethyl)anilines and methyl halophenyl ketones and their cyclization products 2-(halophenyl)quinolin-4-amines
  作者：Lucjan Strekowski、Lubomir Janda、Steven E Patterson、Johnny Nguyen

  DOI：10.1016/0040-4020(95)01110-2

  日期：1996.2

  title ketimines containing a fluorine atom at position 2 of the phenyl group are efficiently cyclized under mild conditions to N-[2-(dimethylamino)ethyl]-2-(2-fluorophenyl)quinolin-4-amines by the reaction with a lithium reagent derived from N,N-dimethylethylenediamine. The facile regioselective displacement of C2-F in the presence of another fluorine atom at the phenyl group by the same reagent or

  通过与锂的反应，在温和的条件下将在苯基的第2位上含有氟原子的标题酮亚胺有效地环化为N- [2-（二甲基氨基）乙基] -2-（2-氟苯基）喹啉-4-胺。由N，N-二甲基乙二胺衍生的试剂。通过相同的试剂或N-硫代-N在苯基上存在另一个氟原子的情况下C2-F的区域选择性迁移用复杂诱导邻近效应（CIPE）过程解释了较高温度下的'-甲基哌嗪。CIPE工艺可在环化为喹啉之前通过反应性更高的哌嗪试剂对2-氟苯基酮亚胺进行胺化。2-氯苯基衍生物在CIPE辅助胺化反应中的反应性要低得多。
• New triple-helix DNA stabilizing agents
  作者：Lucjan Strekowski、Maryam Hojjat、Ewa Wolinska、Alesia N. Parker、Ekaterina Paliakov、Tadeusz Gorecki、Farial A. Tanious、W.David Wilson

  DOI：10.1016/j.bmcl.2004.12.019

  日期：2005.2

  Several substituted quinolin-4-amines and heteroaromatic analogs were synthesized and evaluated for interaction with triplex polydA.2polydT and duplex polydA.polydT by using UV-thermal melting experiments. Excellent triple-helix DNA ligands with high affinity toward T.A.T triplets and triple/duplex selectivity were designed through a rational approach.

  合成了几种取代的喹啉-4-胺和杂芳族类似物，并通过紫外-热熔融实验评估了其与三链体polydA.2polydT和双链体polydA.polydT的相互作用。通过合理的方法设计了对TAT三联体具有高亲和力和三重/双重选择性的优秀三重螺旋DNA配体。
• Synthesis of 2-phenylquinolin-4-amines substituted with diverse amino and aminoalkyl groups
  作者：Martial Say、Ekaterina Paliakov、Maged Henary、Lucjan Strekowski

  DOI：10.1002/jhet.5570430628

  日期：2006.11

  Facile synthetic approaches to 2-phenylquinolin-4-amines containing an aminoalkyl group at N4 of the quinolin-4-amine and amino or aminoalkyl groups at the phenyl moiety are presented.

  提出了一种容易的合成方法，用于合成在喹啉-4-胺的N 4处具有氨基烷基和在苯基部分具有氨基或氨基烷基的2-苯基喹啉-4-胺。
• A Novel Synthetic Route to 1,3-Disubstituted Naphthalenes
  作者：Lucjan Strekowski、Roman L. Wydra、Alexander S. Kiselyov、John H. Baird、Andrew Burritt、James M. Coxon

  DOI：10.1080/00397919408013825

  日期：1994.1

  Abstract 1-(2-Substituted 1-propenyl)-2-(trifluoromethyl)benzenes are cyclized to 3-substituted 1-(4-methylpiperazino)naphthalenes in a lithium 4-methylpiperazide-mediated reaction that involves the trifluoromethyl group.

  摘要 1-(2-取代的1-丙烯基)-2-(三氟甲基)苯在涉及三氟甲基的4-甲基哌嗪锂介导的反应中环化为3-取代的1-(4-甲基哌嗪基)萘。
• Synthesis and Characterization of Titanium Complexes Containing Potentially Tridentate Amido‐cyclopentadienyl Ligands
  作者：Jun Okuda、Karen E. Du Plooy、Werner Massa、Hak‐chul Kang、Ulrich Rose

  DOI：10.1002/cber.19961290305

  日期：1996.3

  Two new titanium complexes of the general type Ti(η5:η1-C5H4SiMe2NCH2CH2X)Cl2 (X = NMe2 OMe), containing a tridentate ligand, were prepared by reaction of Ti(η5-C5H4SiMe2Cl)Cl3 with the lithium amide Li(NHCH2CH2X) (X = NMe2, OMe). The 1HNMR chemical shifts for the protons of the ethylene link were found to vary considerably as a function of the temperature, indicating the presence of an equilibrium

  的一般类型的两个新的钛络合物的Ti（η 5：η 1 -C 5 ħ 4森达2 NCH 2 CH 2 X）氯2（X = NME 2 OME），含有三齿配体，是由钛的反应而制备（ η 5 -C 5 H ^ 4森达2 Cl）的氯3与氨基化锂的Li（NHCH 2 CH 2 X）（X = NME 2，OME）。在1发现乙烯键的质子的HNMR化学位移随温度的变化而显着变化，表明配体的三键和二齿键合模式之间存在平衡。Ti的单晶X-射线结构分析（η 5：η 1 Ç 5 ħ 4森达2 NCH 2 CH 2 OME）氯2显示，该甲氧基函数不是分子内的固态协调。