4-oxo-2-phenacyl-4-phenyl-butyric acid | 77953-17-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-oxo-2-phenacyl-4-phenyl-butyric acid
• 英文别名: 4-Oxo-2-phenacyl-4-phenyl-buttersaeure；α.ε-Dioxo-α.ε-diphenyl-pentan-γ-carbonsaeure；β.β'-Dibenzoyl-isobuttersaeure；Diphenacylessigsaeure；1,5-Diphenyl-3-carboxy-pentandion-(1,5)；Diphenacyl-essigsaeure；4-Oxo-2-(2-oxo-2-phenylethyl)-4-phenylbutanoic acid；4-oxo-2-phenacyl-4-phenylbutanoic acid
• CAS: 77953-17-4
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: YSXGPYZKEDCAMT-UHFFFAOYSA-N

物化性质

• 熔点：
  130-132 °C
• 沸点：
  537.3±45.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2918300090

反应信息

• 作为反应物：
  描述：

  4-oxo-2-phenacyl-4-phenyl-butyric acid 在 tetraphosphorus decasulfide 、 硫酸 、 phosphorus pentoxide 作用下， 以 xylene 、 苯 为溶剂， 反应 4.0h， 生成 2,6-Diphenyl-4H-thiopyran-4-carboxylic acid methyl ester
  参考文献：
  名称：

  1,5-二芳基-3,3-二取代-1,5-戊二酮 - 2,4,6-三取代杂环的合成子

  摘要：

  2,4,6-三取代的杂环是通过 1,5-二芳基-3,3-二甲氧基羰基,5-戊烷二酮 (1) 和 1 中的 ^e/n-二取代基和酮基官能团的官能化制备的,5-二芳基-3-cyano3-ethoxycarbonyl-1,5-pentanedione (4)。简介：碳-碳键形成反应对于设计所需的分子结构很重要。在碳框架内掺杂杂原子构成了杂环的发展。在我们努力制备一类新的杂环时，我们报道了苯甲酰溴在不同条件下与活性亚甲基化合物的反应性。在我们在该领域的研究期间，我们已经从上述底物制备了 1,5-二芳基 3,3-二取代-1,5-戊二酮。1、在 DMSO 中用 NaCl 处理 1 直接提供 1,5-二芳基-3-甲氧羰基-1,5-戊二酮 (3)。类似地，在DMSO中用NaCl处理1，5-二芳基-3-氰基-3-乙氧基羰基-1，5-戊二酮(4)得到1，5-二芳基-3-氰基-1，5-戊二酮(5)。化合物 4 在

  DOI：

  10.1515/hc.2003.9.6.599
• 作为产物：
  描述：

  (phenacylthio)acetic acid 在 sodium hydroxide 作用下， 生成 4-oxo-2-phenacyl-4-phenyl-butyric acid
  参考文献：
  名称：

  Holmberg, Arkiv foer Kemi, 1936, vol. 12 A, # 9, p. 10

  摘要：

  DOI：

文献信息

• Klobb, Bulletin de la Societe Chimique de France, 1900, vol. <3>23, p. 521
  作者：Klobb

  DOI：——

  日期：——
• Klobb, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1900, vol. 130, p. 1254
  作者：Klobb

  DOI：——

  日期：——
• Bougault, Annales de Chimie (Cachan, France), 1908, vol. <8> 15, p. 501
  作者：Bougault

  DOI：——

  日期：——
• Synthesis of substituted 2- and 4-carboxypyrylium salts
  作者：N. V. Kholodova、Yu. P. Andreichikov、G. N. Dorofeenko

  DOI：10.1007/bf00507235

  日期：1981.2
• Ligand-Induced Selectivity in the Rhodium(II)-Catalyzed Reactions of α-Diazo Carbonyl Compounds
  作者：Albert Padwa、David J. Austin、Susan F. Hornbuckle

  DOI：10.1021/jo951576n

  日期：1996.1.1

  3-Allyl-2,5-diazopentanedione and 3-butenyl-2,5-diazopentanedione were allowed to react with a trace amount of a rhodium(II) catalyst in methylene chloride at room temperature. The major products isolated correspond to the internal trapping of a carbonyl ylide as well as intramolecular cyclopropanation. Changing the catalyst from Rh-2(OAc)(4) to Rh-2(cap)(4) to Rh-2(tfa)(4) caused a significant alteration in product distribution. A rather unusual and unexpected regiochemical crossover in the cycloaddition occurred when Rh-2(tfa)(4) was used and is most likely due to complexation of the metal with the dipole. A computational approach to rationalize the observed product distribution was carried out. The thermodynamic stabilities of cycloaddition transition states were approximated from the computationally derived strain energies of ground state molecules using traditional force-field techniques. Globally minimized ground state energies were obtained for all possible cycloaddition products, and final strain energies were calculated. In all cases studied, the lower energy isomer corresponded to the cycloadduct actually isolated. A study of the regiochemical aspects of the Rh(II)-catalyzed reaction of 1-diazo-3-(2-oxo-2-phenylethyl)hexane-2, was also carried out. Cyclization of the initially formed rhodium carbenoid occurred exclusively across the acetyl rather than the benzoyl group. The structure of the internal cycloadduct was assigned on the basis of a proton-detected multiple-bond heteronuclear multiple-quantum coherence experiment.