N-methoxy-N-methyl-3-(2-nitrophenyl)prop-2-enamide | 1090605-53-0

• 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: N-methoxy-N-methyl-3-(2-nitrophenyl)prop-2-enamide
• CAS: 1090605-53-0
• 化学式: C₁₁H₁₂N₂O₄
• mdl: MFCD11732288
• 分子量: 236.227
• InChiKey: LEHYIRPYDVBOMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methoxy-N-methyl-3-(2-nitrophenyl)prop-2-enamide 在 tin(ll) chloride 作用下， 生成
  参考文献：
  名称：

  The insulin secretory action of novel polycyclic guanidines: Discovery through open innovation phenotypic screening, and exploration of structure–activity relationships

  摘要：

  We report the discovery of the glucose-dependent insulin secretogogue activity of a novel class of polycyclic guanidines through phenotypic screening as part of the Lilly Open Innovation Drug Discovery platform. Three compounds from the University of California, Irvine, 1-3, having the 3-arylhexahydropyrrolo[1,2-c] pyrimidin-1-amine scaffold acted as insulin secretagogues under high, but not low, glucose conditions. Exploration of the structure-activity relationship around the scaffold demonstrated the key role of the guanidine moiety, as well as the importance of two lipophilic regions, and led to the identification of 9h, which stimulated insulin secretion in isolated rat pancreatic islets in a glucose-dependent manner. (C) 2014 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.01.021
• 作为产物：
  描述：

  N-甲氧基-N-甲基-2-(三苯基磷)乙酰胺N-甲氧基-N-甲基-2-(三苯基磷)乙酰胺 、 邻硝基苯甲醛 以 二氯甲烷 为溶剂， 反应 16.0h， 以90%的产率得到N-methoxy-N-methyl-3-(2-nitrophenyl)prop-2-enamide
  参考文献：
  名称：

  N-杂环卡宾催化β-取代丙烯酰胺的对映选择性Rauhut-Currier反应

  摘要：

  β-取代的丙烯酰胺具有低亲电性，尚未在对映选择性 Rauhut-Currier 反应中得到利用。通过利用酰胺和中等亲核N中的吸电子保护-杂环卡宾，这种衬底都被转换为对映体富集喹诺酮类。该反应以完全的非对映选择性、良好的产率和适度的对映选择性进行。据报道，衍生化以及计算研究支持通过氮的吸电子保护降低酰胺键特性。

  DOI：

  10.1021/acs.orglett.1c03554

文献信息

• Highly efficient and environmentally benign preparation of Weinreb amides in the biphasic system 2-MeTHF/water
  作者：Vittorio Pace、Laura Castoldi、Andrés R. Alcántara、Wolfgang Holzer

  DOI：10.1039/c3ra41262h

  日期：——

  A straightforward chromatography-free preparation of Weinreb amides starting from acid halides has been achieved in the biphasic medium 2-MeTHF/water. Analytically pure compounds were isolated in excellent yields simply after removal of 2-MeTHF, which absolutely avoids the use of any contaminant organic solvent within the whole process due to its (practically) immiscibility with water.

  在 2-MeTHF/ 水的双相介质中，实现了从酸性卤化物开始的 Weinreb 酰胺的直接无色谱制备。由于 2-MeTHF 与水（实际上）不相溶，因此在整个制备过程中完全避免了使用任何污染性有机溶剂。
• Enantioselective Rauhut–Currier Reaction with β-Substituted Acrylamides Catalyzed by N-Heterocyclic Carbenes
  作者：Venkatachalam Pitchumani、Martin Breugst、David W. Lupton

  DOI：10.1021/acs.orglett.1c03554

  日期：2021.12.17

  acrylamides have low electrophilicity and are yet to be exploited in the enantioselective Rauhut–Currier reaction. By exploiting electron-withdrawing protection of the amide and moderate nucleophilicity N-heterocyclic carbenes, such substrates have been converted to enantioenriched quinolones. The reaction proceeds with complete diastereoselectivity, good yield, and modest enantioselectivity. Derivatizations

  β-取代的丙烯酰胺具有低亲电性，尚未在对映选择性 Rauhut-Currier 反应中得到利用。通过利用酰胺和中等亲核N中的吸电子保护-杂环卡宾，这种衬底都被转换为对映体富集喹诺酮类。该反应以完全的非对映选择性、良好的产率和适度的对映选择性进行。据报道，衍生化以及计算研究支持通过氮的吸电子保护降低酰胺键特性。
• The insulin secretory action of novel polycyclic guanidines: Discovery through open innovation phenotypic screening, and exploration of structure–activity relationships
  作者：Michael B. Shaghafi、David G. Barrett、Francis S. Willard、Larry E. Overman

  DOI：10.1016/j.bmcl.2014.01.021

  日期：2014.2

  We report the discovery of the glucose-dependent insulin secretogogue activity of a novel class of polycyclic guanidines through phenotypic screening as part of the Lilly Open Innovation Drug Discovery platform. Three compounds from the University of California, Irvine, 1-3, having the 3-arylhexahydropyrrolo[1,2-c] pyrimidin-1-amine scaffold acted as insulin secretagogues under high, but not low, glucose conditions. Exploration of the structure-activity relationship around the scaffold demonstrated the key role of the guanidine moiety, as well as the importance of two lipophilic regions, and led to the identification of 9h, which stimulated insulin secretion in isolated rat pancreatic islets in a glucose-dependent manner. (C) 2014 The Authors. Published by Elsevier Ltd.