N,N'-bis(2-benzoyl-1-methylethylidene)ethylenediamine | 24334-81-4

• 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,N'-bis(2-benzoyl-1-methylethylidene)ethylenediamine
• 英文别名: 3,8-dimethyl-1,10-diphenyl-4,7-diaza-2,8-decadiene-1,10-dione；N,N'-bis(2-benzoyl-1-methylethenyl)-1,2-ethanediamine；N,N'-ethylenebis(3-amino-1-phenylbut-2-en-1-one)；1,2-di(2-benzoyl-1-methylvinylamino)ethane；N,N'-ethylenebis(benzoylacetoimine)；N,N'-bis-(1-methyl-3-oxo-3-phenyl-propenyl)-ethylenediamine；N,N'-bis(2-benzoyl-1-methylethenyl)-1,2-ethane-diamine；3-[2-[(4-oxo-4-phenylbut-2-en-2-yl)amino]ethylamino]-1-phenylbut-2-en-1-one
• CAS: 24334-81-4
• 化学式: C₂₂H₂₄N₂O₂
• 分子量: 348.445
• InChiKey: LYGBXGSNXHEWQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-硝基偶氮苯 、 N,N'-bis(2-benzoyl-1-methylethylidene)ethylenediamine 在 sodium acetate 作用下， 以 乙醇 为溶剂， 以35%的产率得到(Z)-3-{2-[(Z)-1-Methyl-2-(4-nitro-phenylazo)-3-oxo-3-phenyl-propenylamino]-ethylamino}-2-(4-nitro-phenylazo)-1-phenyl-but-2-en-1-one
  参考文献：
  名称：

  Opozda, Ewa; Sledziewska, Ewa, Journal fur praktische Chemie (Leipzig 1954), 1991, vol. 333, # 4, p. 607 - 612

  摘要：

  DOI：
• 作为产物：
  描述：

  1-phenylbut-2-yn-1-ol 在 manganese(IV) oxide 作用下， 以 乙醇 为溶剂， 生成 N,N'-bis(2-benzoyl-1-methylethylidene)ethylenediamine
  参考文献：
  名称：

  Bol'shedvorskaya,R.L. et al., Journal of Organic Chemistry USSR (English Translation), 1972, vol. 8, p. 1927 - 1931

  摘要：

  DOI：

文献信息

• A Green Solventless Protocol for the Synthesis of<i>β</i>-Enaminones and<i>β</i>-Enamino Esters Using Silica Sulfuric Acid as a Highly Efficient, Heterogeneous and Reusable Catalyst
  作者：Alireza Hasaninejad、Abdolkarim Zare、Mohammad Rez Mohammadizadeh、Mohsen Shekouhy、Ahmad Reza Moosavi-Zare

  DOI：10.1155/2010/829547

  日期：——

  Silica sulfuric acid is utilized as a green, highly efficient, heterogeneous and recyclable catalyst for the preparation ofβ-enaminones andβ-enamino esters from amines andβ-dicarbonyl compounds under solvent-free conditions at 80 °C. Using this method, the title compounds are produced in high to excellent yields and in short reaction times.

  硅硫酸被用作绿色、高效、非均相且可回收的催化剂，用于在80°C的无溶剂条件下从胺和β-二羰基化合物制备β-烯酮和β-烯胺酯。利用这种方法，所述化合物以高产率至极好的产率和短反应时间制备。
• Cerium(III) Chloride Heptahydrate (CeCl3 · 7H2O) as an Efficient Enamination Catalyst in Aqueous Media
  作者：M. M. Khodaei、A. R. Khosropour、M. Kookhazadeh

  DOI：10.1007/s11178-005-0363-z

  日期：2005.10

  Cerium(III) chloride heptahydrate CeCl3 · H2O catalyzes enamination of β-dicarbonyl compounds with primary amines in aqueous medium at room temperature to afford the corresponding β-enamino ketones with high chemoselectivity.

  七水合氯化铈(III) CeCl3 · 7H2O 在室温下于水相中催化β-二羰基化合物与一级胺的烯胺化反应，以高化学选择性得到相应的β-烯胺酮。
• Nano-SiO2 catalyzed synthesis of β-enaminones under solvent free conditions
  作者：Heshmatollah Alinezhad、Mahmood Tajbakhsh、Malihe Norouzi Sarkati、Mahboobe Zare

  DOI：10.1007/s00706-016-1654-5

  日期：2016.9

  AbstractNano-SiO2 efficiently catalyzed the synthesis of β-enaminones using direct condensation of various (cyclic and acyclic) β-diketones with aromatic and aliphatic amines under solvent-free conditions. This eco-friendly catalyst can be recovered and reused without significant loss of activity. This methodology provides a simple synthetic route to enaminones in excellent yields at room temperature. Graphical

  摘要在无溶剂条件下，使用各种（环状和无环）β-二酮与芳族和脂族胺直接缩合，纳米SiO 2有效催化了β-烯酮的合成。这种环保型催化剂可以回收和再利用，而不会显着降低活性。该方法提供了一种简单的合成途径，可在室温下以优异的产率合成烯胺酮。 图形概要
• The role of a Lewis acid in the Nenitzescu indole synthesis
  作者：Valeriya S. Velezheva、Andrey I. Sokolov、Albert G. Kornienko、Konstantin A. Lyssenko、Yulia V. Nelyubina、Ivan A. Godovikov、Alexander S. Peregudov、Andrey F. Mironov

  DOI：10.1016/j.tetlet.2008.09.087

  日期：2008.12

  A highly efficient Lewis acid-catalyzed method for the Nenitzescu synthesis of 5-hydroxyindoles with a range of substituents at N-1 and C-3 and symmetric 5,5′-dihydroxydiindoles has been developed. The amount of the catalyst (10–100 mol %) required depended on the nature of the enaminone component. It has been shown that Lewis acid plays a role in enaminone component activation through an enamine-ZnC12

  已开发出一种高效的路易斯酸催化方法，用于Nenitzescu合成在N-1和C-3处具有一系列取代基和对称5,5'-二羟基二吲哚的5-羟基吲哚。所需的催化剂量（10–100 mol％）取决于烯胺酮组分的性质。已经显示路易斯酸通过烯胺-ZnCl 2络合物随后去质子化在烯胺酮组分活化中起作用。
• Enamination of β-Dicarbonyl Compounds Catalyzed by CeCl₃·7H₂O at ­Ambient Conditions: Ionic Liquid and Solvent-Free Media
  作者：Mohammad Khodaei、Ahmad Khosropour、Mehdi Kookhazadeh

  DOI：10.1055/s-2004-830879

  日期：——

  Enamination of a wide various primary amines was successfully carried out in the presence of catalytic amounts of cerium chloride heptahydrate in ionic liquid and solvent-free conditions as 'green' media under mild reaction conditions.

  在离子液体中催化量的七水氯化铈和无溶剂条件下，在温和的反应条件下，作为“绿色”介质，成功地进行了多种伯胺的烯化。