(E)-methyl 3-(4-chlorophenyl)-2-((isopropylamino)methyl)acrylate

• 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-((isopropylamino)methyl)acrylate
• 英文别名: methyl (E)-3-(4-chlorophenyl)-2-[(propan-2-ylamino)methyl]prop-2-enoate
• 化学式: C₁₄H₁₈ClNO₂
• 分子量: 267.755
• InChiKey: MMWJGPSQZQEZEI-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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-((isopropylamino)methyl)acrylate 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以69%的产率得到(E)-3-(4-chlorobenzylidene)-1-isopropylazetidin-2-one
  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
• 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 1.0h， 生成 (E)-methyl 3-(4-chlorophenyl)-2-((isopropylamino)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

• Synthesis of Methyl 3-Aryl 2-Isopropyl-aminomethylpropanoates Through Reduction of Methyl 3-Aryl 2-Isopropyl Aminomethylacrylates
  作者：Farid El Guemmout、Mohamed Akssira、Andre Foucaud

  DOI：10.1080/00397919408011492

  日期：1994.2
• 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.