(E)-methyl 3-(4-chlorophenyl)-2-((phenylamino)methyl)acrylate | 786669-29-2

• 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: (E)-methyl 3-(4-chlorophenyl)-2-((phenylamino)methyl)acrylate
• 英文别名: methyl (E)-2-(anilinomethyl)-3-(4-chlorophenyl)prop-2-enoate
• CAS: 786669-29-2
• 化学式: C₁₇H₁₆ClNO₂
• 分子量: 301.773
• InChiKey: HKWUQBXHSQBYHY-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-methyl 3-(4-chlorophenyl)-2-((phenylamino)methyl)acrylate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 (E)-2-(anilinomethyl)-3-(4-chlorophenyl)prop-2-enoic acid
  参考文献：
  名称：

  Synthesis of 4b,5,10a,11-tetrahydroindeno[1,2-b]quinolin-10-ones from Baylis–Hillman adducts

  摘要：

  We developed an efficient synthetic method for indenoquinoline skeletons from Baylis-Hillman adducts. 4b,5,10a,11-Tetrahydroindeno[1,2-b]quinolin-10-ones and 7H-indeno[2,1-c]quinolines were prepared from Baylis-Hillman adducts in polyphosphoric acid. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.075
• 作为产物：
  描述：

  2-[(4-氯苯基)-羟基甲基]-丙烯酸甲酯 在 硫酸 、 氢溴酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 (E)-methyl 3-(4-chlorophenyl)-2-((phenylamino)methyl)acrylate
  参考文献：
  名称：

  Design, synthesis and evaluation of 3-arylidene azetidin-2-ones as potential antifungal agents against Alternaria solani Sorauer

  摘要：

  A new concise and facile method was explored to synthesize a collection of new 3-arylidene azetidin-2-ones, which could be regarded as the derivatives of the hybrid scaffold of bioactive natural cinnamamide and heterocycle azetidi-2-one. The structures of the synthesized compounds were characterized by H-1, C-13 NMR, and MS; and their antifungal activity were evaluated against Alternaria solani Sorauer. These antifungal data were subjected to a quantitative structure-activity relationship (QSAR) analysis using Codessa software on the basis of the results from B3LYP/6-31G(d,p) quantum calculations. The best regressive model revealed that potentially more active compounds should have low dipole moments and Q(C-min) (minimal net atomic charge for a C atom), and high Q(O-max) (maximal net atomic charge for an O atom) and Q(N-min) (minimal net atomic charge for an N atom). The most potent compound 7k could lead to intracellular accumulation of reactive oxygen species, dissipation of mitochondrial transmembrane potential, and an autophagy-like cell death process in A. solani Sorauer. Taken together, these results laid the foundation for further design of improved crop-protection agents based on this hybrid scaffold. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.11.003

文献信息

• Cerium(IV) ammonium nitrate catalyzed synthesis of α-dehydro-β-amino esters
  作者：Moumita Paira、Samir Kumar Mandal、Subhas Chandra Roy

  DOI：10.1016/j.tetlet.2008.02.054

  日期：2008.4

  α-Dehydro-β-amino esters have been synthesized regioselectively from acetates of Baylis–Hillman adducts with amines in the presence of a catalytic amount of ceric ammonium nitrate (CAN) in good yield. The regioselectivity does not differ with respect to the polarity of the solvent.

  在催化量的硝酸铈铵（CAN）的存在下，由Baylis-Hillman加合物与胺的乙酸区域选择性合成α-脱氢-β-氨基酯。区域选择性相对于溶剂的极性没有不同。
• Oxidative Heck Coupling of Allylic Amines with 2,2,6,6‐Tetramethylpiperidine‐ <i>N</i> ‐oxyl (TEMPO) as Oxidant for the Preparation of Tetrasubstituted Alkenes
  作者：Zhiheng He、Birgit Wibbeling、Armido Studer

  DOI：10.1002/adsc.201300846

  日期：2013.12.16

  AbstractThe paper describes the oxidative Heck arylation of various allylic amines using arylboronic acids for the preparation of tetrasubstituted alkenes. As oxidant the commercially available 2,2,6,6‐tetramethylpiperidine‐N‐oxyl (TEMPO) is used and coupling reactions occur under very mild conditions at room temperature. The densely substituted alkenes are formed in good to excellent yields with complete control of the diastereoselectivity. Substrate scope with respect to the allylic amine and the arylboronic acid is investigated.magnified image
• Design, synthesis and evaluation of 3-arylidene azetidin-2-ones as potential antifungal agents against Alternaria solani Sorauer
  作者：Wang Delong、Wu Yongling、Wang Lanying、Feng Juntao、Zhang Xing

  DOI：10.1016/j.bmc.2017.11.003

  日期：2017.12

  A new concise and facile method was explored to synthesize a collection of new 3-arylidene azetidin-2-ones, which could be regarded as the derivatives of the hybrid scaffold of bioactive natural cinnamamide and heterocycle azetidi-2-one. The structures of the synthesized compounds were characterized by H-1, C-13 NMR, and MS; and their antifungal activity were evaluated against Alternaria solani Sorauer. These antifungal data were subjected to a quantitative structure-activity relationship (QSAR) analysis using Codessa software on the basis of the results from B3LYP/6-31G(d,p) quantum calculations. The best regressive model revealed that potentially more active compounds should have low dipole moments and Q(C-min) (minimal net atomic charge for a C atom), and high Q(O-max) (maximal net atomic charge for an O atom) and Q(N-min) (minimal net atomic charge for an N atom). The most potent compound 7k could lead to intracellular accumulation of reactive oxygen species, dissipation of mitochondrial transmembrane potential, and an autophagy-like cell death process in A. solani Sorauer. Taken together, these results laid the foundation for further design of improved crop-protection agents based on this hybrid scaffold. (C) 2017 Elsevier Ltd. All rights reserved.
• Synthesis of 4b,5,10a,11-tetrahydroindeno[1,2-b]quinolin-10-ones from Baylis–Hillman adducts
  作者：Chang Gon Lee、Ka Young Lee、Saravanan GowriSankar、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2004.08.075

  日期：2004.9

  We developed an efficient synthetic method for indenoquinoline skeletons from Baylis-Hillman adducts. 4b,5,10a,11-Tetrahydroindeno[1,2-b]quinolin-10-ones and 7H-indeno[2,1-c]quinolines were prepared from Baylis-Hillman adducts in polyphosphoric acid. (C) 2004 Elsevier Ltd. All rights reserved.