(Z)-ethyl 3-(4-nitrophenyl)-3-oxo-2-(3-oxoindolin-2-ylidene)propanoate | 615286-59-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (Z)-ethyl 3-(4-nitrophenyl)-3-oxo-2-(3-oxoindolin-2-ylidene)propanoate
• 英文别名: ethyl (2Z)-3-(4-nitrophenyl)-3-oxo-2-(3-oxo-1H-indol-2-ylidene)propanoate
• CAS: 615286-59-4
• 化学式: C₁₉H₁₄N₂O₆
• 分子量: 366.33
• InChiKey: NFVWWUFZFUOPPN-NXVVXOECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  115.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (Z)-ethyl 3-(4-nitrophenyl)-3-oxo-2-(3-oxoindolin-2-ylidene)propanoate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以50%的产率得到3-(4-Nitro-phenyl)-5H-pyridazino[4,3-b]indole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of pyridazino[4,3-b]indoles and indeno[1,2-c]pyridazines as new ligands of central and peripheral benzodiazepine receptors

  摘要：

  A large number of pyridazino[4,3-b]indoles and indeno[1,2-c]pyridazines were synthesised and tested to evaluate their binding affinities at both central (CBR) and peripheral (PBR) benzodiazepine receptors. Relatively good PBR binding affinities were found for ligands belonging to the 3-arylmethyloxy-pyridazinoindole series, whereas only 2-aryl-indenopyridazines 7a, 8a and 10a display a weak binding affinity for CBR. To find out the main structural determinants affecting PBR affinity, a molecular modelling study based on the comparative analysis of the three-dimensional properties of four properly selected derivatives 24a, 3b, 18a and 10d, with those of highly active and selective PBR ligands, taken as reference, was performed.

  DOI：

  10.1016/s0014-827x(02)00017-4
• 作为产物：
  描述：

  2-氯-3H-吲哚-3-酮 、 3-(4-nitro-phenyl)-3-oxo-propionic acid ethyl ester; sodium compound 以 1,4-二氧六环 为溶剂， 以6.23 g的产率得到(Z)-ethyl 3-(4-nitrophenyl)-3-oxo-2-(3-oxoindolin-2-ylidene)propanoate
  参考文献：
  名称：

  Synthesis and biological evaluation of pyridazino[4,3-b]indoles and indeno[1,2-c]pyridazines as new ligands of central and peripheral benzodiazepine receptors

  摘要：

  A large number of pyridazino[4,3-b]indoles and indeno[1,2-c]pyridazines were synthesised and tested to evaluate their binding affinities at both central (CBR) and peripheral (PBR) benzodiazepine receptors. Relatively good PBR binding affinities were found for ligands belonging to the 3-arylmethyloxy-pyridazinoindole series, whereas only 2-aryl-indenopyridazines 7a, 8a and 10a display a weak binding affinity for CBR. To find out the main structural determinants affecting PBR affinity, a molecular modelling study based on the comparative analysis of the three-dimensional properties of four properly selected derivatives 24a, 3b, 18a and 10d, with those of highly active and selective PBR ligands, taken as reference, was performed.

  DOI：

  10.1016/s0014-827x(02)00017-4

文献信息

• Cu(ii)-catalyzed highly regio- and stereoselective construction of C–C double bonds: an efficient method for the ketonization–olefination of indoles
  作者：Yun-Hong Bao、Jia-Yi Zhu、Wen-Bing Qin、Yu-Bo Kong、Zheng-Wang Chen、Shao-Bin Tang、Liang-Xian Liu

  DOI：10.1039/c3ob41589a

  日期：——

  A general and efficient method for the cross-coupling of indoles with β-keto esters by using TEMPO/CuSO4·5H2O in air as oxidant has been developed. This reaction features high functional-group compatibility and an excellent selectivity. This methodology provides an alternative approach for the ketonization–olefination of indoles in moderate to good yields.

  以 TEMPO/CuSO4Â-5H2O 为氧化剂，在空气中进行吲哚与δ-酮酯的交叉偶联，开发出了一种通用而高效的方法。该反应具有较高的官能团兼容性和出色的选择性。该方法为吲哚的酮化烯化反应提供了另一种方法，且收率适中。
• Synthesis and biological evaluation of pyridazino[4,3-b]indoles and indeno[1,2-c]pyridazines as new ligands of central and peripheral benzodiazepine receptors
  作者：Francesco Campagna、Fausta Palluotto、Maria Paola Mascia、Elisabetta Maciocco、Carla Marra、Angelo Carotti、Antonio Carrieri

  DOI：10.1016/s0014-827x(02)00017-4

  日期：2003.2

  A large number of pyridazino[4,3-b]indoles and indeno[1,2-c]pyridazines were synthesised and tested to evaluate their binding affinities at both central (CBR) and peripheral (PBR) benzodiazepine receptors. Relatively good PBR binding affinities were found for ligands belonging to the 3-arylmethyloxy-pyridazinoindole series, whereas only 2-aryl-indenopyridazines 7a, 8a and 10a display a weak binding affinity for CBR. To find out the main structural determinants affecting PBR affinity, a molecular modelling study based on the comparative analysis of the three-dimensional properties of four properly selected derivatives 24a, 3b, 18a and 10d, with those of highly active and selective PBR ligands, taken as reference, was performed.