(Z)-1-(4-chlorophenyl)-3-(phenylamino)prop-2-en-1-one

• 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-(4-chlorophenyl)-3-(phenylamino)prop-2-en-1-one
• 英文别名: (2Z)-1-(4-chlorophenyl)-3-(phenylamino)prop-2-en-1-one；(Z)-3-anilino-1-(4-chlorophenyl)prop-2-en-1-one
• 化学式: C₁₅H₁₂ClNO
• 分子量: 257.719
• InChiKey: VZCSLOHTERTVCE-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 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：

  2,4-二苯基-3-丁炔-2-醇 、 (Z)-1-(4-chlorophenyl)-3-(phenylamino)prop-2-en-1-one 在 三氟化硼乙醚 作用下， 以 硝基甲烷 为溶剂， 反应 1.0h， 以94%的产率得到(4-chlorophenyl)(6-methyl-1,4,6-triphenyl-1,6-dihydropyridin-3-yl)methanone
  参考文献：
  名称：

  路易斯酸与炔丙醇催化烯胺酮的环化反应：多取代1,2-二氢吡啶的区域选择性合成

  摘要：

  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。

  DOI：

  10.1021/jo4005553
• 作为产物：
  描述：

  3-dimethylamino-1(4-chloro-phenyl)-2-propen-1-one 、 苯胺 在 iron(III) chloride 、 水 作用下， 反应 2.0h， 以91%的产率得到(Z)-1-(4-chlorophenyl)-3-(phenylamino)prop-2-en-1-one
  参考文献：
  名称：

  Water-Promoted Synthesis of Enaminones: Mechanism Investigation and Application in Multicomponent Reactions

  摘要：

  Highly stereoselective synthesis of Z-enaminones bearing reactive secondary amino group has been successfully performed in water using tertiary amino group functionalized enaminones under ambient conditions. An interesting promotion effect of water on the reaction via hydrolysis-dehydration condensation has been observed through a designed isotope labeling experiment. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.715712

文献信息

• A facile one-pot synthesis of tetrahydropyrimidines part 3 Synthesis of [alkanediylbis(3-alkyl/aralkyl/aryl-3,6-dihydropyrimidine-1,5(2<i>H</i>)-diyl)bis(arylmethanones) and [1,4-phenylenebis(3-phenyl-3,6-dihydropyrimidine-1,5(2<i>H</i>)-diyl)]bis(phenylmethanone)
  作者：Milan CH. Dutta、Kaushik Chanda、Jai N. Vishwakarma

  DOI：10.1002/jhet.5570420118

  日期：2005.1

  A facile one-pot synthetic strategy has been developed for novel [alkanediylbis(3-alkyl/aralkyl/ aryl-3,6-dihydropyrimidine-1,5(2H)-diyl)]bis(arylmethanones) 2a-c, 2e-m and [1,4-phenylenebis(3-phenyl-3,6-dihydropyrimidine-1,5(2H)-diyl)]bis(phenylmethanone) 2d by refluxing enaminones 1a-f in methanol with diamines and formaldehyde.

  已经开发了一种简便的一锅合成策略，用于新型[烷二基双（3-烷基/芳烷基/芳基-3,6-二氢嘧啶-1,5（2 H）-二基）]双（芳基甲酮）2a-c，2e- m和[1,4-亚苯基双（3-苯基-3,6-二氢嘧啶-1,5（2 H）-二基）]双（苯基甲酮）2d通过在甲醇中将烯胺酮1a-f与二胺和甲醛回流而制得。
• Features of reactions of (E)-1-(β-aroylvinyl)pyridinium bromides with binucleophiles
  作者：R. Dzh. Khachikyan、Z. G. Ovakimyan、G. A. Panosyan、R. A. Tamazyan、A. G. Ayvazyan

  DOI：10.1134/s1070363216070070

  日期：2016.7

  Regardless of pH and a solvent nature the reactions of (E)-1-(beta-aroylvinyl)pyridinium bromides with hydrazine led to the formation of pyrazole derivatives. The salts reacted with thiourea via intermediate formation of 4-arylpyrimidine-2-thiol to give (Z)-2-[(beta-aroylvinyl)sulfanyl]-4-arylpyrimidines. In the case of N,N'-diphenylthiourea the reaction provided 6-aryl-3-aroyl-1-phenylpyridinium bromides. Pyridine hydrobromide liberated in the reaction course has a major influence on the process chemoselectivity.
• 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。
• Water-Promoted Synthesis of Enaminones: Mechanism Investigation and Application in Multicomponent Reactions
  作者：Yunyun Liu、Rihui Zhou、Jie-Ping Wan

  DOI：10.1080/00397911.2012.715712

  日期：2013.9.17

  Highly stereoselective synthesis of Z-enaminones bearing reactive secondary amino group has been successfully performed in water using tertiary amino group functionalized enaminones under ambient conditions. An interesting promotion effect of water on the reaction via hydrolysis-dehydration condensation has been observed through a designed isotope labeling experiment. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.