(Z)-1-phenyl-3-(phenylamino)prop-2-en-1-one | 25039-25-2

• 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)-1-phenyl-3-(phenylamino)prop-2-en-1-one
• 英文别名: (Z)-3-anilino-1-phenylprop-2-en-1-one
• CAS: 25039-25-2
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: KTJZOKJJOYMVPV-QXMHVHEDSA-N

物化性质

• 熔点：
  141-142 °C(Solv: methanol (67-56-1))
• 沸点：
  358.0±38.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  (Z)-1-phenyl-3-(phenylamino)prop-2-en-1-one 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 S-methyl N-(3-oxo-3-phenyl-propen-1-yl)-N,N'-diphenyl isothiourea
  参考文献：
  名称：

  REACTION OF ENAMINONES WITH THIACUMULENES

  摘要：

  Enaminones 2, easily prepared from the corresponding sodium salts of beta -ketoaldehydes 1 and hydrochlorides of primary amines, react with carbon disulfide/sodium hydride to give dithiocarbamates 3 after alkylation. In a similar way thiocarbamoylation yields isothioureas 4. The C-13 NMR parameters of 2, 3 and 4 show significant low- and high-field shifts of the C-1 and C-2 signals, respectively.

  DOI：

  10.1080/10426509808032471
• 作为产物：
  描述：

  苯乙酮 在 potassium hydrogensulfate 作用下， 以 水 为溶剂， 反应 1.5h， 生成 (Z)-1-phenyl-3-(phenylamino)prop-2-en-1-one
  参考文献：
  名称：

  Devi; Dutta; Nongkhlaw, Journal of the Indian Chemical Society, 2010, vol. 87, # 6, p. 739 - 742

  摘要：

  DOI：

文献信息

• Lewis Acid-Catalyzed Cyclization of Enaminones with Propargylic Alcohols: Regioselective Synthesis of Multisubstituted 1,2-Dihydropyridines
  作者：Yushang Shao、Kai Zhu、Zhengchen Qin、Ende Li、Yanzhong Li

  DOI：10.1021/jo4005553

  日期：2013.6.7

  A highly efficient BF3·Et2O-catalyzed cascade reaction of enaminones with propargylic alcohols under mild reaction conditions has been developed. This methodology offers regioselective access to multisubstituted 1,2-dihydropyridines in good to excellent yields.

  在温和的反应条件下，开发了高效的BF 3 ·Et 2 O催化烯胺酮与炔丙醇的级联反应。该方法提供了对多取代的1,2-二氢吡啶的区域选择性访问，收率好至极佳。
• 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。
• Conjugate Addition of 3-Buytn-2-one to Anilines in Ethanol: Alkene Geometric Insights through In Situ FTIR Monitoring
  作者：David R. Chisholm、Roy Valentine、Ehmke Pohl、Andrew Whiting

  DOI：10.1021/acs.joc.6b01110

  日期：2016.9.2

  A convenient, mild and effective conjugate addition of 3-butyn-2-one to a variety of anilines in ethanol is reported. The reaction was monitored and characterized through in situ FTIR, and the dynamics of the facile E/Z alkene geometry interconversion of the resultant aniline-derived enaminones was explored through NMR, FTIR and X-ray crystallography. A straightforward purification protocol that employs

  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。
• Novel Regioselectivity: Three-Component Cascade Synthesis of Unsymmetrical 1,4- and 1,2-Dihydropyridines
  作者：Jie-Ping Wan、Shi-Feng Gan、Gong-Lei Sun、Yuan-Jiang Pan

  DOI：10.1021/jo900068z

  日期：2009.4.3

  of α,β-unsaturated aldehydes, amines, and enaminones proceeded smoothly to give 1,3,4-trisubstituted 1,4-dihydropyridines in aqueous DMF. Moreover, the unexpected regioselective formation of 1,2-dihydropyridines has been observed for the first time in such an approach. On the basis of a systematic study, the novel regioselectivity could be assigned both to steric and electronic effects originating from

  α，β-不饱和醛，胺和烯胺酮的三组分顺序反应平稳进行，得到在DMF水溶液中的1,3,4-三取代的1,4-二氢吡啶。此外，在这种方法中首次观察到了1，2-二氢吡啶的意外的区域选择性形成。在系统研究的基础上，可以将新的区域选择性分配给源自胺配偶体的空间和电子效应。
• Silver-mediated aminophosphinoylation of propargyl alcohols with aromatic amines and H-phosphine oxides leading to α-aminophosphine oxides
  作者：Qiang Huang、Lei Zhu、Dong Yi、Xiaohui Zhao、Wei Wei

  DOI：10.1016/j.cclet.2019.07.049

  日期：2020.2

  H-phosphine oxides for the construction of α-aminophosphine oxides has been developed. The C N and C P bond could be efficiently formed in one pot operation via sequential C C and C O bond cleavage of propargylic alcohols. This present methodology, which not only provides a simple and alternative strategy for the synthesis of α-aminophosphine oxides, but also opens a new window for the cleavage reactions of

  摘要研究了一种新的银介导的炔丙醇的氨基膦酰基与芳族胺和H-膦氧化物的合成，用于α-氨基膦氧化物的构建。通过连续进行炔丙醇的CC和CO键裂解，可以在一锅操作中有效地形成CN和CP键。本方法学不仅为合成α-氨基膦氧化物提供了一种简单且可替代的策略，而且为通过脱醛基化偶联进行炔丙醇的裂解反应开辟了新的窗口。