(E)-N,N-diethyl-3-(2-methoxyphenyl)acrylamide | 1184304-17-3

• 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: (E)-N,N-diethyl-3-(2-methoxyphenyl)acrylamide
• 英文别名: N,N-diethyl-3-(2-methoxyphenyl)acrylamide；(E)-N,N-diethyl-3-(2-methoxyphenyl)prop-2-enamide
• CAS: 1184304-17-3
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: KPZOLYMDGUOCOZ-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  碘仿 、 (E)-N,N-diethyl-3-(2-methoxyphenyl)acrylamide 在 chromium dichloride 、 铁粉 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以68%的产率得到(1S*,2R*,3S*)-N,N-diethyl-2-iodo-3-(2-methoxyphenyl)cyclopropanecarboxamide
  参考文献：
  名称：

  高效催化铬介导的碘代环丙烷化反应：碘代环丙烷甲酰胺的立体选择性合成

  摘要：

  据报道，催化铬介导的碘代环丙烷甲酰胺的新型合成。该反应可以在芳族（E）-或（Z）-α，β-不饱和酰胺上进行，其中CC双键被二或三取代。该过程具有完全的立体特异性，并且以高的立体选择性产生了新的CI立体中心。还报道了所得碘代环丙烷甲酰胺的一些合成应用。通过X射线分析确定了碘代丙烷和衍生物的结构。

  DOI：

  10.1002/adsc.201000574
• 作为产物：
  描述：

  邻甲氧基苯甲醛 在 哌啶 、 吡啶 、 三乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (E)-N,N-diethyl-3-(2-methoxyphenyl)acrylamide
  参考文献：
  名称：

  Identification and optimization of piperine analogues as neuroprotective agents for the treatment of Parkinson’s disease via the activation of Nrf2/keap1 pathway

  摘要：

  Parkinson's disease (PD) is a slowly progressive and complex neurodegenerative disorder. Up to date, there are no approved drugs that could slow or reverse the neurodegenerative process of PD. Here, we reported the synthesis of series of piperine analogues and the evaluation of their neuroprotective effects against hydrogen peroxide (H2O2) induced damage in the neuron-like PC12 cells. Among these analogues, 3b exhibited the most potent protection effect and its underlying mechanism was further investigated. Further results indicated that the ROS scavenging and cytoprotection effect of 3b might be related to the Nrf2 activation and upregulation of related phase II antioxidant enzymes, such as HO-1 and NQO1. In in vivo study, oral administration (100 mg/kg) of 3b significantly attenuated PD-associated behavioral deficits in a 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced mouse model of PD and protected tyrosine hydroxylase-immunopositive dopaminergic neurons. Our results provided evidence that 3b might be a promising candidate for Parkinson's disease treatment. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112385

文献信息

• Microwave-assisted one-pot synthesis of a, β-unsaturated amides under solvent-free conditions
  作者：Shilei Jiang、Yuanyuan Xie、Xiaochun Yu

  DOI：10.3184/030823409x393682

  日期：2009.1

  Under microwave-assisted solvent-free conditions a one-pot reaction of triphenylphosphine, an aldehyde and N, N-diethyl chloroacetamide in the presence of zinc dust affords α, β-unsaturated amides stereoselectively in good yield. In comparison with the conventional heating method, the reaction was finished within five minutes under microwave irradiation.

  在微波辅助的无溶剂条件下，三苯基膦、醛和 N, N-二乙基氯乙酰胺在锌粉存在下的一锅反应以良好的收率立体选择性地提供了 α, β-不饱和酰胺。与传统的加热方法相比，在微波照射下，反应在五分钟内完成。
• Electron-Catalyzed Aminocarbonylation: Synthesis of α,β-Unsaturated Amides from Alkenyl Iodides, CO, and Amines
  作者：Baptiste Picard、Takahide Fukuyama、Takanobu Bando、Mamoru Hyodo、Ilhyong Ryu

  DOI：10.1021/acs.orglett.1c03714

  日期：2021.12.17

  Aminocarbonylation of alkenyl iodides with CO and amines proceeded under heating to produce α,β-unsaturated amides in good yields (23 examples, 71% average yield). This catalyst-free method exhibited good functional-group tolerance, and open a straightforward access to functionalized acrylamides, as illustrated by the synthesis of Ilepcimide. A hybrid radical/ionic mechanism involving chain electron transfer is

  烯基碘与 CO 和胺的氨基羰基化在加热下进行，以良好的产率（23 个实例，71% 的平均产率）产生 α,β-不饱和酰胺。这种无催化剂的方法表现出良好的官能团耐受性，并打开了对官能化丙烯酰胺的直接访问，如 Ilepcimide 的合成所示。针对这种转变提出了一种涉及链式电子转移的混合自由基/离子机制。
• Synthesis of α,β-Unsaturated Amide via Phosphonium Ylide
  作者：Shilei Jiang、Kefeng Yang、Xiaochun Yu

  DOI：10.1080/00397910802590902

  日期：2009.4.22

  A series of ,-unsaturated amides were prepared by the Wittig reaction of N,N-diethylamidemethylenetriphenylphosphorane ylide with aldehydes with moderate to good yields.
• Identification and optimization of piperine analogues as neuroprotective agents for the treatment of Parkinson’s disease via the activation of Nrf2/keap1 pathway
  作者：Lun Wang、Xiaoying Cai、Mingsong Shi、Linlin Xue、Shuang Kuang、Ruiling Xu、Wenyan Qi、Yan Li、Xu Ma、Ruijia Zhang、Feng Hong、Haoyu Ye、Lijuan Chen

  DOI：10.1016/j.ejmech.2020.112385

  日期：2020.8

  Parkinson's disease (PD) is a slowly progressive and complex neurodegenerative disorder. Up to date, there are no approved drugs that could slow or reverse the neurodegenerative process of PD. Here, we reported the synthesis of series of piperine analogues and the evaluation of their neuroprotective effects against hydrogen peroxide (H2O2) induced damage in the neuron-like PC12 cells. Among these analogues, 3b exhibited the most potent protection effect and its underlying mechanism was further investigated. Further results indicated that the ROS scavenging and cytoprotection effect of 3b might be related to the Nrf2 activation and upregulation of related phase II antioxidant enzymes, such as HO-1 and NQO1. In in vivo study, oral administration (100 mg/kg) of 3b significantly attenuated PD-associated behavioral deficits in a 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced mouse model of PD and protected tyrosine hydroxylase-immunopositive dopaminergic neurons. Our results provided evidence that 3b might be a promising candidate for Parkinson's disease treatment. (C) 2020 Elsevier Masson SAS. All rights reserved.
• An Efficient Catalytic Chromium-Mediated Iodocyclopropanation Reaction: Stereoselective Synthesis of Iodocyclopropanecarboxamides
  作者：José M. Concellón、Humberto Rodríguez-Solla、Elena G. Blanco、Santiago García-Granda、and M. Rosario Díaz

  DOI：10.1002/adsc.201000574

  日期：2011.1.10

  catalytic chromium‐mediated novel synthesis of iodocyclopropanecarboxamides is reported. This reaction can be carried out on aromatic (E)‐ or (Z)‐α,β‐unsaturated amides in which the CC double bond is di‐ or trisubstituted. This process takes place with total stereospecificity and the new CI stereogenic center is generated with high stereoselectivity. Some synthetic applications of the obtained iodocyclopropanecarboxamides

  据报道，催化铬介导的碘代环丙烷甲酰胺的新型合成。该反应可以在芳族（E）-或（Z）-α，β-不饱和酰胺上进行，其中CC双键被二或三取代。该过程具有完全的立体特异性，并且以高的立体选择性产生了新的CI立体中心。还报道了所得碘代环丙烷甲酰胺的一些合成应用。通过X射线分析确定了碘代丙烷和衍生物的结构。