propan-2-yl 3-anilino-3-phenylprop-2-enoate | 148180-94-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: propan-2-yl 3-anilino-3-phenylprop-2-enoate
• CAS: 148180-94-3
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: ZMIPFAAWSZCXPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  423.5±45.0 °C(Predicted)
• 密度：
  1.120±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3,3,3-三氟丙酮酸乙酯 、 propan-2-yl 3-anilino-3-phenylprop-2-enoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以95%的产率得到iso-propyl 4-hydroxy-5-oxo-1,2-diphenyl-4-(trifluoromethyl)-4,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  A facile synthesis of 3-hydroxy-3-(trifluoromethyl)-1H-pyrrol-2(3H)-ones with Brønsted acid-catalyzed condensation–cyclization reactions of β-enamino esters and ethyl trifluoropyruvate

  摘要：

  A facile synthesis of 3-hydroxy-3-(trifluoromethyl)-1H-pyrrol-2(3H)-ones based on trifluoroacetic acid-catalyzed condensation-cyclization reactions of beta-enamino esters and ethyl trifluoropyruvate is described. These reactions afford a series of alpha-trifluoromethylated gamma-lactam compounds in good to excellent yields under mild conditions. A preliminary trial of an asymmetric catalytic version with chiral BINOL-derived phosphoric acid as enantioselective catalyst was conducted and showed promising enantioselectivity of the desired product. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.052
• 作为产物：
  描述：

  isopropyl 3-oxo-3-(phenyl)propanoate 、 苯胺 在 溶剂黄146 作用下， 生成 propan-2-yl 3-anilino-3-phenylprop-2-enoate
  参考文献：
  名称：

  N-芳基烯胺在可见光辐射下可持续合成2-芳基-3-羧酸二氢吲哚

  摘要：

  在室温下用可见光照射催化量的Ir（ppy）3，可以将许多N-芳基烯胺以良好至极佳的收率转化成其相应的吲哚啉产物，而无需任何额外的添加剂。这是在可见光照射下通过烯胺的分子内环化合成二氢吲哚的第一个实例。

  DOI：

  10.1039/c7cc04358a

文献信息

• A sustainable synthesis of 2-aryl-3-carboxylate indolines from N-aryl enamines under visible light irradiation
  作者：Cheng-Juan Wu、Wen-Xiao Cao、Tao Lei、Zhi-Hua Li、Qing-Yuan Meng、Xiu-Long Yang、Bin Chen、Vaidhyanathan Ramamurthy、Chen-Ho Tung、Li-Zhu Wu

  DOI：10.1039/c7cc04358a

  日期：——

  light irradiation of catalytic amount of Ir(ppy)3 at room temperature, a number of N-aryl enamines were transformed to their corresponding indoline products in good to excellent yields without requiring any extra additives. This is the first example to synthesize indolines via intramolecular cyclization of enamines under visible light irradiation.

  在室温下用可见光照射催化量的Ir（ppy）3，可以将许多N-芳基烯胺以良好至极佳的收率转化成其相应的吲哚啉产物，而无需任何额外的添加剂。这是在可见光照射下通过烯胺的分子内环化合成二氢吲哚的第一个实例。
• A facile synthesis of 3-hydroxy-3-(trifluoromethyl)-1H-pyrrol-2(3H)-ones with Brønsted acid-catalyzed condensation–cyclization reactions of β-enamino esters and ethyl trifluoropyruvate
  作者：Qing-Lan Pei、Bao-Dong Cui、Wen-Yong Han、Zhi-Jun Wu、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1016/j.tet.2014.05.052

  日期：2014.8

  A facile synthesis of 3-hydroxy-3-(trifluoromethyl)-1H-pyrrol-2(3H)-ones based on trifluoroacetic acid-catalyzed condensation-cyclization reactions of beta-enamino esters and ethyl trifluoropyruvate is described. These reactions afford a series of alpha-trifluoromethylated gamma-lactam compounds in good to excellent yields under mild conditions. A preliminary trial of an asymmetric catalytic version with chiral BINOL-derived phosphoric acid as enantioselective catalyst was conducted and showed promising enantioselectivity of the desired product. (C) 2014 Elsevier Ltd. All rights reserved.
• Lewis Acid-Relayed Singlet Oxygen Reaction with Enamines: Selective Dimerization of Enamines to Pyrrolin-4-ones
  作者：Tao Lei、Yuan-Yuan Cheng、Xu Han、Chao Zhou、Bing Yang、Xiu-Wei Fan、Bin Chen、Chen-Ho Tung、Li-Zhu Wu

  DOI：10.1021/jacs.2c07450

  日期：2022.9.14

  oxidative dimerization of enamines to produce pyrrolin-4-ones in good to excellent yields. Mechanistic studies reveal the formation of the imino ketone intermediate from the interaction of 1O2 and enamine, which is able to interact with Lewis acid, relaying the 1O2 reaction in enamine chemistry. For the first time, selective cross-dimerization of two different enamines is achieved. Due to the advantages

  单线态氧 ( 1 O 2 ) 介导的氧化代表了一种有吸引力的策略，可以在温和和环境友好的条件下结合空气中的氧原子。然而，与烯胺的1 O 2反应会发生碎片化，导致转化非常不成功。在这里，路易斯酸被引入以拦截1 O 2反应的 [2 + 2] 或“烯”反应中间体，并使烯胺的氧化二聚化以良好至优异的产率产生 pyrrolin-4-one。机理研究揭示了亚氨基酮中间体的形成来自1 O 2的相互作用和烯胺，它能够与路易斯酸相互作用，在烯胺化学中传递1 O 2反应。首次实现了两种不同烯胺的选择性交叉二聚化。由于条件温和、化学选择性高、收率高达 99% 等优点，已开发出一种在环境条件下合成氮杂杂环化合物的有前景的策略，可进一步用于咪唑酮、喹喔啉和高度官能化亚胺的合成.