(Z)-4-(phenylamino)but-3-en-2-one | 60390-89-8

• 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: (Z)-4-(phenylamino)but-3-en-2-one
• 英文别名: (Z)-4-anilinobut-3-en-2-one
• CAS: 60390-89-8
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: PKPHRGDDGVWMSF-FPLPWBNLSA-N

物化性质

• 沸点：
  282.6±32.0 °C(Predicted)
• 密度：
  1.080±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4-(6-methoxy-1-oxo-tetralin-2-yl)but-2-enal 、 (Z)-4-(phenylamino)but-3-en-2-one 在 sodium sulfate 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到2-((3-acetyl-1-phenyl-1,4-dihydropyridin-4-yl)methyl)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  Access to Highly Enantioenriched Donepezil-like 1,4-Dihydropyridines as Promising Anti-Alzheimer Prodrug Candidates via Enantioselective Tsuji Allylation and Organocatalytic Aza-Ene-Type Domino Reactions

  摘要：

  This work aims at exploiting both the enantioselective Tsuji allylation of allyl carbonate 6 and an organocatalytic aza-ene-type domino reaction between enal 3a and beta-enaminone 4a to develop a straightforward access to all of the four possible stereoisomers of a donepezil-like 1,4-dihydropyridine 1a (er up to 99.5:0.5; overall yield up 64%), an anti-Alzheimer's prodrug candidate. This strategy was extended to the preparation of other enantioenriched 1,4-dihydropyridines 1b-i (eight examples), highlighting its potential in the development of these chiral AChE inhibitors.

  DOI：

  10.1021/acs.joc.8b01442
• 作为产物：
  描述：

  4-phenylamino-3-buten-2-one 以 重水 为溶剂， 反应 48.0h， 生成 (Z)-4-(phenylamino)but-3-en-2-one
  参考文献：
  名称：

  通过乙醇原位FTIR监测，将3-Buytn-2-one与乙醇苯胺共轭：烯烃的几何学见解

  摘要：

  据报道，在乙醇中向各种苯胺中方便，温和，有效地将3-butyn-2-one共轭加成。通过原位FTIR对反应进行监测和表征，并通过NMR，FTIR和X射线晶体学研究所得苯胺衍生的烯胺酮的简便E / Z烯烃几何结构相互转化的动力学。鉴定了采用直接Kugelrohr蒸馏的直接纯化方案，该方法进一步扩展到其他胺和炔酮，可快速获得这些有趣的化合物。

  DOI：

  10.1021/acs.joc.6b01110

文献信息

• Palladium-Catalyzed Intermolecular Oxidative Coupling Reactions of (<i>Z</i>)-Enamines with Isocyanides through Selective β-C(sp²)-H and/or C=C Bond Cleavage
  作者：Weigao Hu、Jia Zheng、Meng Li、Wanqing Wu、Haiyang Liu、Huanfeng Jiang

  DOI：10.1002/cjoc.201800127

  日期：2018.8

  two efficient palladium‐catalyzed intermolecular oxidative coupling reactions of (Z)‐enamines with isocyanides via selective β‐C(sp2)‐H and/or C=C bond cleavage have been developed, leading to controllable chemodivergent and stereoselective construction of a wide range of (E)‐β‐carbamoylenamine derivatives containing strong intramolecular hydrogen bonds. Furthermore, possible reaction pathways for these

  本文中，已开发出两种有效的钯催化（Z）-烯胺与异氰酸酯通过选择性β-C（sp 2）-H和/或C = C键裂解的分子间氧化偶联反应，从而导致可控的化学扩散和立体选择性结构多种包含强分子内氢键的（E）-β-氨基甲酰亚胺衍生物。此外，在初步机理研究的基础上，提出了这些转化的可能反应途径。
• A Method for the Preparation of β-Amino-α,β-unsaturated Carbonyl Compounds: Study of Solvent Effect and Mechanism
  作者：Reyno R. S.、Akash Sugunan、Ranganayakulu S.、Cherumuttathu H. Suresh、Goreti Rajendar

  DOI：10.1021/acs.orglett.9b04531

  日期：2020.2.7

  An efficient method for the preparation of β-amino-α,β-unsaturated carbonyl compounds is demonstrated. Bench-stable sodium 3-oxo-enolates were prepared from carbonyl compounds, and reacted with amines in the presence of an acid and a desiccant. DFT studies revealed contrasting mechanisms toward the reactivity of aliphatic amines in protic solvents and aromatic amines in aprotic solvents. While the

  证明了一种制备β-氨基-α，β-不饱和羰基化合物的有效方法。由羰基化合物制备稳定的3-氧代-烯醇钠盐，并在酸和干燥剂的存在下与胺反应。DFT研究揭示了质子溶剂中脂族胺与质子溶剂中芳族胺反应性的对比机制。前者通过形成亚胺进行，而后者通过迈克尔加成消除机理进行。
• “On water” reaction of deactivated anilines with 4-methoxy-3-buten-2-one, an effective butynone surrogate
  作者：Meriam Jebari、Karine Pasturaud、Baptiste Picard、Jacques Maddaluno、Farhat Rezgui、Isabelle Chataigner、Julien Legros

  DOI：10.1039/c6ob02402e

  日期：——

  (Z)-Enaminones are easily synthesized from poorly nucleophilic anilines and 4-methoxy-3-buten-2 one (an effective and inexpensive surrogate for 3-butyn-2-one) with impressive “on water” acceleration.

  （Z）-烯醇酮可以很容易地从难以亲核的苯胺和4-甲氧基-3-丁烯-2-酮（一种有效且廉价的3-丁炔-2-酮替代物）合成，并且在水上表现出令人印象深刻的加速效果。
• Ruthenium Complexes of Electronically Coupled Cyclopentadienone Ligands – Catalysts for Transformations of Propargyl Alcohols
  作者：Edgar Haak

  DOI：10.1002/ejoc.200700064

  日期：2007.6

  A series of donor- and acceptor-substituted ruthenium cyclopentadienone complexes were synthesized and their catalytic activities towards propargyl alcohols focused on amination reactions have been investigated. It is shown that the substituents of the cyclopentadienone ligand determine the mode of activation of propargyl alcohols by these complexes leading to different central intermediates in catalytic

  合成了一系列供体和受体取代的钌环戊二烯酮配合物，并研究了它们对专注于胺化反应的炔丙醇的催化活性。结果表明，环戊二烯酮配体的取代基决定了这些配合物对炔丙醇的活化模式，导致催化循环中的不同中心中间体。可以实现炔丙醇向α-或β-氨基酮、烯氨基酮、α,β-不饱和亚胺、酮、烯烃和共轭烯炔的催化转化。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Ruthenium-Catalyzed Enaminoketone Formation from Propargyl Alcohols
  作者：Edgar Haak

  DOI：10.1055/s-2006-947357

  日期：2006.8

  Monomeric ruthenium(O) complexes containing electronically coupled dienone ligands were found to catalyze the formation of enaminoketones from propargyl alcohols.

  发现含有电子偶联二烯酮配体的单体钌（O）配合物可催化炔丙醇形成烯氨基酮。