lithium N-benzyl-N-methylamide

• 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: lithium N-benzyl-N-methylamide
• 英文别名: lithium;benzyl(methyl)azanide
• 化学式: C₈H₁₀N*Li
• 分子量: 127.115
• InChiKey: JNAZXACBZPSDMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.81
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  lithium N-benzyl-N-methylamide 在 三氯化磷 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  调谐磷空洞对末端炔烃催化交叉二聚的评价

  摘要：

  描述了四个新的双磷空洞体的合成，包括它们在末端炔烃的交叉二聚反应中的催化用途的描述。将市售的P [N（CH 2 CH 3）2 ] 3，PhP [N（CH 2 CH 3）2 ] 2，P（OCH 3）3以及原位生成的P（NMeBn）3与四氟甲烷反应。 -ol cavitand平台可提供新的磷配体。这些配体容易形成双-Au络合物，经检查可生成反应性谱，用于末端炔烃的催化交叉二聚。我们发现，配体衍生自P [N（CH 3）2 ] 3具有最佳的产品选择性。

  DOI：

  10.1016/j.tetlet.2016.09.039
• 作为产物：
  描述：

  isopropenyllithium 、 3,4-二甲氧基-3-环丁烯-1,2-二酮 、 生成 lithium N-benzyl-N-methylamide 、 、 (3AS,4S,6AR)-6A-{[Benzyl(methyl)amino]methyl}-3A-hydroxy-2,3-dimethoxy-4-methyl-4,5,6,6A-tetrahydro-1(3AH)-pentalenone
  参考文献：
  名称：

  Evaluation of Amino Substituents as Nucleofugal Controllers of Regioselectivity and as Chelate Modulators of Stereoselectivity in Squarate Ester Cascades

  摘要：

  The tandem addition of an alkenyllithium reagent and a 2-lithioallylamine to squarate esters has been systematically examined. The effect of the sequencing of this twofold addition has been investigated. The extent to which the amino group is eliminated was found to be dependent on the structural features of the companion nucleophile. Also assessed was the comparative ease with which the amino and methoxy groups experience competitive beta-elimination from the highly reactive, medium-ring dianionic intermediates. Attempts were made to curtail the level of competing 1,4-addition, and success was achieved by increasing the effective size of the O-alkyl groups in the squarate ester. The highly stereocontrolled transformations described represent a notably direct means for producing highly fused polycyclic compounds, Mechanistic considerations sm rounding these reactions, which are characterized by an impressive enhancement of molecular scaffolding, are discussed.

  DOI：

  10.1021/jo9722919

文献信息

• Synthesis of α-Amino Acids via a Carbolithiation Reaction on Acyclic Ene-Carbamates and an Internal N→C Alkyloxycarbonyl Migration
  作者：Isabelle Gillaizeau、Gérard Coudert、Bertrand Cottineau、Julien Farard、Marie-Laure Auclair

  DOI：10.1055/s-2007-984874

  日期：2007.7

  A novel and efficient synthesis of precursors of α-amino acids is described. The key step involves a carbolithiation reaction on acyclic ene-carbamates generated from the corresponding vinylphosphates via a palladium cross-coupling reaction followed by a spontaneous internal N→C alkyloxycarbonyl migration.

  描述了一种新型有效的 α-氨基酸前体合成方法。关键步骤涉及通过钯交叉偶联反应由相应的乙烯基磷酸酯生成的无环烯氨基甲酸酯的碳锂化反应，然后是自发的内部 N→C 烷氧基羰基迁移。
• A General Synthesis of Amines and Hydrazines by Oxidation of Amidocuprates and Zinc-Amidocuprates
  作者：F. Canè、D. Brancaleoni、P. Dembech、A. Ricci、G. Seconi

  DOI：10.1055/s-1997-1218

  日期：1997.5

  A wide range of amines and hydrazines were synthesized according to an electrophilic amination protocol by oxidative decomposition of readily generated lithium- and zinc-amidocyanocuprates. Optimization of the yields was achieved by the appropriate combination of the organometallic cluster and the nature of the oxidizing agent.

  通过氧化分解容易生成的锂氨氰酸酯和锌氨氰酸酯，根据亲电氨基化协议合成了多种胺和肼。通过有机金属簇和氧化剂性质的适当组合，实现了产率的优化。
• Oxidative Intramolecular Coupling of Amidocuprates as a Novel Route to Amines and Hydrazines
  作者：Angelo Alberti、Francesco Canè、Pasquale Dembech、Dario Lazzari、Alfredo Ricci、Giancarlo Seconi

  DOI：10.1021/jo9512315

  日期：1996.1.1

  Amidocuprates, derived from organocopper reagents and lithium amides upon exposure to oxygen at low temperature, provide new amine derivatives in satisfactory yields. Details of this flexible and simple methodology are given. The reaction mechanism is analyzed in terms of an oxidative intramolecular coupling of aminyl radicals with the ligands on Cu in the intermediate amidocuprate. This reaction is

  在低温下暴露于氧气时，衍生自有机铜试剂和酰胺化锂的酰胺基铜酸盐可提供令人满意的产率的新胺衍生物。给出了这种灵活而简单的方法的详细信息。根据胺基自由基与中间酰胺基铜酸盐中Cu上的配体的氧化性分子内偶联来分析反应机理。该反应是用于N-烷基化，-乙烯基化和-芳基化的温和而有效的方法，通过该方法可以合成许多不易通过常规途径获得的胺。一旦应用于酰肼锂，它也为N-取代的肼提供了新的直接途径。
• Cyclic beta-amino acid derivatives as factor Xa inhibitors
  申请人：Corte R. James

  公开号：US20060074103A1

  公开（公告）日：2006-04-06

  The present application describes cyclic β-amino acid derivatives or pharmaceutically acceptable salt forms thereof, wherein the central core is a non-aromatic carbocycle or heterocycle. Compounds of the present invention are useful as inhibitors of trypsin-like serine proteases, specifically factor Xa.

  本申请描述了环状β-氨基酸衍生物或其药用可接受的盐形式，其中中心核心为非芳香族碳环或杂环。本发明的化合物可用作胰蛋白酶样丝氨酸蛋白酶抑制剂，特别是对凝血因子Xa。
• METHOD FOR PREPARING CHEMICAL COMPOUNDS OF INTEREST BY NUCLEOPHILIC AROMATIC SUBSTITUTION OF AROMATIC CARBOXYLIC ACID DERIVATIVES SUPPORTING AT LEAST ONE ELECTRO-ATTRACTIVE GROUP
  申请人：Mortier Jacques

  公开号：US20120316337A1

  公开（公告）日：2012-12-13

  Method for preparing carboxylic acid derivatives by aromatic nucleophilic substitution, in which a carboxylic acid derivative having a single carboxyl functional group, or one of the salts thereof, the carboxylic acid derivative having, in the ortho position of the carboxyl functional group, a leaving group, which is preferably an atom of fluorine or of chlorine or an alkoxy group, chiral or not, preferably a methoxy group, the carboxylic acid derivative not being substituted by an electro attractive group other than the leaving group if any; is reacted with a reactant MNu, where M is a metal and Nu is a nucleophile, chiral or not, the aromatic nucleophilic substitution reaction being carried out without a catalyst and without a step of protecting/deprotecting the acid functional group of the starting compound.

  用芳香族亲核取代法制备羧酸衍生物的方法，其中一种具有单个羧基官能团的羧酸衍生物或其盐之一，该羧酸衍生物在羧基官能团的邻位上具有一个离去基团，该离去基团优选为氟原子或氯原子或烷氧基，手性或非手性，优选为甲氧基，该羧酸衍生物如果有离去基团，则不被其他电子吸引基团所取代；与反应物MNu反应，其中M是金属，Nu是亲核试剂，手性或非手性，芳香族亲核取代反应在无催化剂和无保护/脱保护起始化合物的酸官能团步骤的情况下进行。