α-benzoyl-2,3-dihydro-2-hydroxy-1,3-dioxo-1H-indene-2-acetic acid ethyl ester | 72872-53-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-benzoyl-2,3-dihydro-2-hydroxy-1,3-dioxo-1H-indene-2-acetic acid ethyl ester
• 英文别名: ethyl 2-(2–hydroxy-1,3-dioxo-2,3-dihydro-1H-inden-2-yl)−3-oxo-3-phenylpropanoate；Ethyl 2-(2-hydroxy-1,3-dioxoinden-2-yl)-3-oxo-3-phenylpropanoate
• CAS: 72872-53-8
• 化学式: C₂₀H₁₆O₆
• 分子量: 352.343
• InChiKey: SUAYLIMYBOXOTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  97.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  α-benzoyl-2,3-dihydro-2-hydroxy-1,3-dioxo-1H-indene-2-acetic acid ethyl ester 在 一水合肼 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 3.0h， 生成 5-Oxo-3-phenyl-5H-indeno[1,2-c]pyridazine-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Inhibition of Monoamine Oxidase-B by 5H-Indeno[1,2-c]pyridazines: Biological Activities, Quantitative Structure-Activity Relationships (QSARs) and 3D-QSARs

  摘要：

  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).

  DOI：

  10.1021/jm00019a018
• 作为产物：
  描述：

  水合茚三酮 、 ethyl benzoylacetate 以 水 为溶剂， 反应 15.0h， 以72%的产率得到α-benzoyl-2,3-dihydro-2-hydroxy-1,3-dioxo-1H-indene-2-acetic acid ethyl ester
  参考文献：
  名称：

  Peet, Norton P.; Huber, Edward W.; Huffman, John C., Journal of Heterocyclic Chemistry, 1995, vol. 32, # 1, p. 33 - 42

  摘要：

  DOI：

文献信息

• Straightforward green synthesis of indeno-furan carboxylates from ninhydrin and β-ketoesters: X-Ray crystal structure, Hirshfeld and DFT investigations
  作者：Ahmed T.A. Boraei、Saied M. Soliman、Matti Haukka、Eid E. Salama、Manar Sopaih、Assem Barakat、Ahmed A.M. Sarhan

  DOI：10.1016/j.molstruc.2022.132433

  日期：2022.5

  investigated. Indeno[1,2-b]furan-3-carboxylate 3 was obtained from ethyl acetoacetate via stirring in water for 15 min, whereas, in case of ethyl benzoylacetate afforded the 2-(2‑hydroxy-1,3-dioxo-2,3-dihydro-1H-inden-2-yl)-3-oxo-3-phenylpropanoate 2 in water for longer time about 6 h . Reaction of ninhydrin with ethyl benzoylacetate in a mixture of acetic acid/water/methanol afforded the compound 4

  研究了茚三酮对β-酮酯反应的多样性。茚并[1,2 - b ]呋喃-3-羧酸酯3是由乙酰乙酸乙酯通过在水中搅拌15分钟得到的，而在苯甲酰乙酸乙酯的情况下得到2-(2-羟基-1,3-dioxo-2 ,3-dihydro-1 H -inden-2-yl)-3-oxo-3-phenylpropanoate 2在水中较长时间约 6 小时。茚三酮与苯甲酰乙酸乙酯在乙酸/水/甲醇的混合物中反应得到化合物4. 使用 Hirshfeld 计算分析了控制所研究晶体结构的分子堆积的不同类型的分子间相互作用。结果揭示了 O…H、H…H 和 H…C 相互作用对晶体稳定性的重要性。使用 DFT 计算预测最小能量结构，并发现与相应的 X 射线结构非常匹配。计算并比较了电子特性HOMO、LUMO、偶极矩、MEP（分子静电势）图和分子反应性描述符。计算了 GIAO NMR 化学位移，结果与实验数据具有良好的相关性，相关系数接近
• Carotti,A. et al., Gazzetta Chimica Italiana, 1979, vol. 109, p. 329 - 333
  作者：Carotti,A. et al.

  DOI：——

  日期：——