11H-indeno[1,2-c]cinnolin-11-one | 13239-36-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 11H-indeno[1,2-c]cinnolin-11-one
• 英文别名: 11H-Indeno<1,2-c>cinnolin-11-on；indeno[1,2-c]cinnolin-11-one；Indeno[1,2-c]cinnolin-11-one
• CAS: 13239-36-6
• 化学式: C₁₅H₈N₂O
• 分子量: 232.241
• InChiKey: MNWYNMNNUMFSGM-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  473.3±38.0 °C(predicted)
• 密度：
  1.404±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-乙炔基-2-氟苯 在 bis-triphenylphosphine-palladium(II) chloride 、 silver hexafluoroantimonate 、 copper(l) iodide 、 盐酸肼 、 二苯基亚砜 、 caesium carbonate 、 二异丙胺 、 三苯基膦 、 copper dichloride 、 palladium dichloride 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 甲苯 为溶剂， 反应 37.08h， 生成 11H-indeno[1,2-c]cinnolin-11-one
  参考文献：
  名称：

  Palladium(ii)-catalyzed synthesis of functionalized indenones via oxidation and cyclization of 2-(2-arylethynylphenyl)acetonitriles

  摘要：

  已经开发了一种一锅两步合成多功能烯酮的工艺。该钯(II)催化的转化过程涉及使用Ph2SO作为氧化剂，从2-(2-芳基乙炔基苯基)乙腈生成并缩合邻位功能化的1,2-苯基酮。所得到的3-氰基烯酮可以转化为各种有价值的分子。

  DOI：

  10.1039/c3ob40103k

文献信息

• Inhibition of Monoamine Oxidase-B by 5H-Indeno[1,2-c]pyridazines: Biological Activities, Quantitative Structure-Activity Relationships (QSARs) and 3D-QSARs
  作者：Silvia Kneubuehler、Ulrike Thull、Cosimo Altomare、Vincenco Carta、Patrick Gaillard、Pierre-Alain Carrupt、Angelo Carotti、Bernard Testa

  DOI：10.1021/jm00019a018

  日期：1995.9

  A large series (66 compounds) of indeno[1,2-c]pyridazin-5-ones (IPs) were synthesized and tested on their monoamine oxidase-A (MAO-A) and MAO-B inhibitory activity. All of the tested compounds acted preferentially on MAO-B displaying weak (nonmeasurable IC50 values) to high (submicromolar IC50 values) activities. The most active compound was p-CF3-3-phenyl-IP (IC50 = 90 nM). Multiple linear regression analysis of the substituted 3-phenyl-IPs yielded good statistical results (q(2) = 0.74; r(2) = 0.86) and showed the importance of lipophilic, electronic, and steric properties of the substituents in determining inhibitory potency. Various comparative molecular field analysis studies were performed with different alignments and including the molecular lipophilicity potential. This led to a model including the steric, electrostatic and lipophilicity fields and having a good predictive value (q(2) = 0.75; r(2) = 0.93).
• Palladium(ii)-catalyzed synthesis of functionalized indenones via oxidation and cyclization of 2-(2-arylethynylphenyl)acetonitriles
  作者：Xuxing Chen、Qian He、Yuyuan Xie、Chunhao Yang

  DOI：10.1039/c3ob40103k

  日期：——

  A one-pot two-step synthesis of versatile indenones has been developed. This palladium(II)-catalyzed transformation involves generation and condensation of ortho-functionalized 1,2-benzils from 2-(2-arylethynylphenyl)acetonitriles using Ph2SO as the oxidant. The resulting 3-cyanoindenones can be converted to various valuable molecules.

  已经开发了一种一锅两步合成多功能烯酮的工艺。该钯(II)催化的转化过程涉及使用Ph2SO作为氧化剂，从2-(2-芳基乙炔基苯基)乙腈生成并缩合邻位功能化的1,2-苯基酮。所得到的3-氰基烯酮可以转化为各种有价值的分子。