(2E)-1-(2'-nitrophenyl)-3-(2-naphthyl)-2-propen-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (2E)-1-(2'-nitrophenyl)-3-(2-naphthyl)-2-propen-1-one
• 英文别名: (E)-3-naphthalen-2-yl-1-(2-nitrophenyl)prop-2-en-1-one
• 化学式: C₁₉H₁₃NO₃
• 分子量: 303.317
• InChiKey: OHGALPZFDVSSFG-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E)-1-(2'-nitrophenyl)-3-(2-naphthyl)-2-propen-1-one 在 十二羰基三钌 、 一氧化碳 、 DIAN-Me 作用下， 以 乙醇 、 水 为溶剂， 170.0 ℃ 、3.04 MPa 条件下， 反应 3.0h， 以52.4%的产率得到2-(naphthalen-2-yl)-2,3-dihydroquinolin-4(1H)-one
  参考文献：
  名称：

  Intramolecular amination of olefins. Synthesis of 2-substituted-4-quinolones from 2-nitrochalcones catalysed by ruthenium

  摘要：

  通过在170°C和30个大气压下用CO还原2-氮基查尔酮1，得到2-取代-4-喹啉2及相应的2,3-二氢-2-取代-4-喹啉3，反应以Ru3(CO)12为催化剂，DIAN-Me作为助催化剂，在乙醇-水中进行。

  DOI：

  10.1039/c39940001741
• 作为产物：
  描述：

  邻硝基苯乙酮 、 2-萘甲醛 在 potassium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 生成 (2E)-1-(2'-nitrophenyl)-3-(2-naphthyl)-2-propen-1-one
  参考文献：
  名称：

  Antihyperglycemic activity of naphthylchalcones

  摘要：

  The purpose of the present work was to investigate, following previous works, naphthylchalcones as antihyperglycemic agent in glucose loaded animal model, insulin secretion as well as the action of these compounds on glucose uptake in a target tissue of insulin. The naphthylchalcones were found to have an acute serum glucose-lowering effect in hyperglycemic normal rats. In addition, chalcones 2 and 4 stimulated significantly the insulin secretion induced by glucose. These results suggest that the presence of nitro group and their position in the phenyl rings are responsible for the antihyperglycemic activity of chalcones. Additionally, the effect of chalcones on serum glucose-lowering seems to be a consequence of insulin secretion and these chalcones represent potential compounds with strong antihyperglycemic properties. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.017

文献信息

• Antihyperglycemic activity of naphthylchalcones
  作者：Rosangela Guollo Damazio、Ana Paula Zanatta、Luisa Helena Cazarolli、Louise Domeneghini Chiaradia、Alessandra Mascarello、Ricardo José Nunes、Rosendo Augusto Yunes、Fátima Regina Mena Barreto Silva

  DOI：10.1016/j.ejmech.2009.12.017

  日期：2010.4

  The purpose of the present work was to investigate, following previous works, naphthylchalcones as antihyperglycemic agent in glucose loaded animal model, insulin secretion as well as the action of these compounds on glucose uptake in a target tissue of insulin. The naphthylchalcones were found to have an acute serum glucose-lowering effect in hyperglycemic normal rats. In addition, chalcones 2 and 4 stimulated significantly the insulin secretion induced by glucose. These results suggest that the presence of nitro group and their position in the phenyl rings are responsible for the antihyperglycemic activity of chalcones. Additionally, the effect of chalcones on serum glucose-lowering seems to be a consequence of insulin secretion and these chalcones represent potential compounds with strong antihyperglycemic properties. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Intramolecular amination of olefins. Synthesis of 2-substituted-4-quinolones from 2-nitrochalcones catalysed by ruthenium
  作者：Stefano Tollari、Sergio Cenini、Fabio Ragaini、Lucia Cassar

  DOI：10.1039/c39940001741

  日期：——

  2-Substituted-4-quinolones 2 and the corresponding 2,3-dihydro-2-substituted-4-quinolones 3 have been obtained by reduction with CO at 170 °C and 30 atm of 2-nitrochalcones 1, catalysed by Ru3(CO)12 with DIAN-Me as co-catalyst in ethanol–water.

  通过在170°C和30个大气压下用CO还原2-氮基查尔酮1，得到2-取代-4-喹啉2及相应的2,3-二氢-2-取代-4-喹啉3，反应以Ru3(CO)12为催化剂，DIAN-Me作为助催化剂，在乙醇-水中进行。