4-phenylamino-3-buten-2-one | 187606-81-1

• 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: 4-phenylamino-3-buten-2-one
• 英文别名: (E)-4-anilino-3-buten-2-one；(E)-4-(phenylamino)but-3-en-2-one；(3E)-4-(phenylamino)but-3-en-2-one；(E)-4-Phenylamino-but-3-en-2-one；(E)-4-anilinobut-3-en-2-one
• CAS: 187606-81-1
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: PKPHRGDDGVWMSF-BQYQJAHWSA-N

物化性质

• 熔点：
  91.5-92.5 °C
• 沸点：
  88 °C(Press: 2 Torr)
• 密度：
  0.9252 g/cm3

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：

  4-phenylamino-3-buten-2-one 在 五氯化磷 作用下， 以 苯 为溶剂， 以56%的产率得到
  参考文献：
  名称：

  Enamino ketones in the synthesis of phosphorus-cointaining heterocycles

  摘要：

  DOI：

  10.1007/s11176-005-0104-6
• 作为产物：
  描述：

  反式-4-甲氧基-3-丁烯-2-酮 、 苯胺 在 scandium(III) triflate 、 特戊醛 作用下， 以 二氯甲烷 为溶剂， 反应 336.0h， 以45%的产率得到4-phenylamino-3-buten-2-one
  参考文献：
  名称：

  A multicomponent formal [1+2+1+2]-cycloaddition for the synthesis of dihydropyridines

  摘要：

  在路易斯酸催化条件下，甲氧基乙烯基甲基酮与不同胺和醛的反应，产生了一种新颖的、正式的、逐步的[1+2+1+2]环加成，从而得到二氢吡啶产品。

  DOI：

  10.1039/c2cc31495a

文献信息

• 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。
• Relay Catalysis To Synthesize β-Substituted Enones: Organocatalytic Substitution of Vinylogous Esters and Amides with Organoboronates
  作者：Sasha Sundstrom、Thien S. Nguyen、Jeremy A. May

  DOI：10.1021/acs.orglett.9b04584

  日期：2020.2.21

  Organocatalysis was shown to facilitate conjugate additions to vinylogous esters and amides for the first time. Subsequent elimination of a β-alcohol or amine provided π-conjugated β-substituted enones. Remarkably, nucleophile addition to the electron-rich vinylogous substrates is more rapid than classical enones, forming monosubstituted products. A doubly organocatalytic (organic diol and methyl aniline)

  首次显示有机催化可促进共轭物添加到乙烯基酯和酰胺中。随后消除β-醇或胺提供了π-缀合的β-取代的烯酮。值得注意的是，亲核试剂向富电子乙烯基底物中的添加要比经典烯酮更快，形成单取代产物。双重有机催化（有机二醇和甲基苯胺）共轭加成反应直接从炔基酮合成了产物。这两种催化转化均与过渡金属催化正交，从而具有良好的收率，易于获得或可商购的试剂，高选择性，试剂回收和可循环利用性，简便的可扩展性以及出色的官能团耐受性。
• Ono, Machiko; Todoriki, Reiko; Tamura, Shinzo, Chemical and pharmaceutical bulletin, 1986, vol. 34, # 2, p. 463 - 470
  作者：Ono, Machiko、Todoriki, Reiko、Tamura, Shinzo

  DOI：——

  日期：——
• Remarkable catalytic effect of H+ in Michael-type additions of anilines to 3-butyn-2-one
  作者：Ik-Hwan Um、Eun-Ju Lee、Ji-Sook Min

  DOI：10.1016/s0040-4020(01)00981-4

  日期：2001.11

  Second-order rate constants (k(N)) for the Michael-type reaction of 3-butyn-2-one (1) with a series of anilines in H2O have been determined spectrophotometrically. The k(N) values are dependent on the free aniline fraction (F-N). The plot of log k(N) vs pK(a) of the conjugate acid of the anilines is linear for the reactions run at F-N=1.00. However, the Bronsted-type plot for the reactions performed at F-N=0.50 is nonlinear, suggesting a change in the reaction mechanism as the basicity of anilines changes. The analysis of the kinetic results has revealed that the reaction of anilines proceeds through the protonated form of the substrate 1 as well as the unprotonated. The protonated form of 1 is of the order of 10(9) times more reactive than the unprotonated form toward anilines. The contribution of the reaction with the protonated species to the k(N) is suggested to be responsible for the nonlinear Bronsted-type plot obtained for the reactions run at F-N=0.50. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Sobanow A. A., Tscherkasow R. A., Zh. obshh. khimii, 64 (1994) N 7, S 1219
  作者：Sobanow A. A., Tscherkasow R. A.

  DOI：——

  日期：——