biphenyl-4-yl-phenyl-acetaldehyde | 163559-72-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: biphenyl-4-yl-phenyl-acetaldehyde
• 英文别名: 2-Oxo-1-phenyl-1-p-diphenylyl-aethan；Biphenyl-4-yl-phenyl-acetaldehyd；Phenyl-p-diphenylyl-acetaldehyd；2-Phenyl-2-(4-phenylphenyl)acetaldehyde；2-phenyl-2-(4-phenylphenyl)acetaldehyde
• CAS: 163559-72-6
• 化学式: C₂₀H₁₆O
• 分子量: 272.346
• InChiKey: PVDUJSODJLXJOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  biphenyl-4-yl-phenyl-acetaldehyde 、 丁烯酮 在 氢氧化钾 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以67.1%的产率得到4-Biphenyl-4-yl-4-phenyl-cyclohex-2-enone
  参考文献：
  名称：

  General Theoretical Treatments of Solid-State Photochemical Rearrangements and a Variety of Contrasting Crystal versus Solution Photochemistry

  摘要：

  In continuing our investigations of control of excited state reactivity by inclusion in crystal lattices, we have encountered a variety of new examples of differing reactivity resulting from lattice restraints. Different theoretical treatments were tested and several proved applicable. Not only could the course of reactions imposed by the crystal lattice be predicted but also the ability to react versus lack of reactivity. For cyclohexenones with C-2 and C-5 substitution, either of two aryl groups at C-4 are available for migration; which one migrates depends on the lattice. One C-2 substituted and seven C-5 substituted cyclohexenones were investigated. Additionally some cyclopentenone photochemistry was investigated. Throughout, programming was developed to generate a ''mini crystal lattice'' having the appropriate space group symmetry and X-ray coordinates and with a central molecule surrounded by reactant molecules. Replacement of the central molecule with a transition state molecule provided a new ''mini-lattice''. Generally, the first diradical intermediate was used to simulate the reaction transition state. The mini-lattice was then subject to study. Overlap of the central, partially reacted species with the surrounding molecules provided one criterion. Molecular motion of the reactant excited state in forming the partially reacted species provided a test of least motion as a second criterion. A third test utilizing MM3 geometry optimization of the reacting species imbedded in the rigid mini-lattice, provided a measure of the increase in intra- and intermolecular energy of this molecule. A final approach determined the points of nearest molecule-lattice approach and mapped these in the form of a ''lock and key''; this has the advantage of indicating which interactions result in inhibition or lack thereof of a particular reaction route. Predicting ability to react proved important since reactivity falls into three categories: (I) no reaction in the lattice, (2) differing reactivity compared to solution, (3) the same behavior in solution. Perturbing an intermediate geometry toward that of the reactant and then determining the deformation energy provided a reactivity measure.

  DOI：

  10.1021/ja00124a008
• 作为产物：
  描述：

  2-(4-biphenylyl)-2-phenyl-oxirane 在 三氟化硼乙醚 作用下， 以 苯 为溶剂， 反应 0.03h， 以92%的产率得到biphenyl-4-yl-phenyl-acetaldehyde
  参考文献：
  名称：

  General Theoretical Treatments of Solid-State Photochemical Rearrangements and a Variety of Contrasting Crystal versus Solution Photochemistry

  摘要：

  In continuing our investigations of control of excited state reactivity by inclusion in crystal lattices, we have encountered a variety of new examples of differing reactivity resulting from lattice restraints. Different theoretical treatments were tested and several proved applicable. Not only could the course of reactions imposed by the crystal lattice be predicted but also the ability to react versus lack of reactivity. For cyclohexenones with C-2 and C-5 substitution, either of two aryl groups at C-4 are available for migration; which one migrates depends on the lattice. One C-2 substituted and seven C-5 substituted cyclohexenones were investigated. Additionally some cyclopentenone photochemistry was investigated. Throughout, programming was developed to generate a ''mini crystal lattice'' having the appropriate space group symmetry and X-ray coordinates and with a central molecule surrounded by reactant molecules. Replacement of the central molecule with a transition state molecule provided a new ''mini-lattice''. Generally, the first diradical intermediate was used to simulate the reaction transition state. The mini-lattice was then subject to study. Overlap of the central, partially reacted species with the surrounding molecules provided one criterion. Molecular motion of the reactant excited state in forming the partially reacted species provided a test of least motion as a second criterion. A third test utilizing MM3 geometry optimization of the reacting species imbedded in the rigid mini-lattice, provided a measure of the increase in intra- and intermolecular energy of this molecule. A final approach determined the points of nearest molecule-lattice approach and mapped these in the form of a ''lock and key''; this has the advantage of indicating which interactions result in inhibition or lack thereof of a particular reaction route. Predicting ability to react proved important since reactivity falls into three categories: (I) no reaction in the lattice, (2) differing reactivity compared to solution, (3) the same behavior in solution. Perturbing an intermediate geometry toward that of the reactant and then determining the deformation energy provided a reactivity measure.

  DOI：

  10.1021/ja00124a008

文献信息

• [EN] NOVEL DIHYDROPYRIMIDIN-2(1H)-ONE COMPOUNDS AS S-NITROSOGLUTATHIONE REDUCTASE INHIBITORS<br/>[FR] NOUVEAUX COMPOSÉS DIHYDROPYRIMIDINE-2(1H)-ONES EN TANT QU'INHIBITEURS DE LA S-NITROSOGLUTATHION RÉDUCTASE
  申请人：N30 PHARMACEUTICALS LLC

  公开号：WO2011038204A1

  公开（公告）日：2011-03-31

  The present invention is directed to novel dihydropyrimidin-2(1H)-one compounds useful as S-nitrosoglutathione reductase (GSNOR) inhibitors, pharmaceutical compositions comprising such compounds, and methods of making and using the same.

  本发明涉及一种新型二氢嘧啶-2(1H)-酮化合物，可用作S-亚硝基谷胱甘肽还原酶（GSNOR）抑制剂，包括这些化合物的药物组合物，以及制备和使用这些化合物的方法。
• Delaville, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1927, vol. 184, p. 463
  作者：Delaville

  DOI：——

  日期：——
• NOVEL DIHYDROPYRIMIDIN-2(1H)-ONE COMPOUNDS AS S-NITROSOGLUTATHIONE REDUCTASE INHIBITORS
  申请人：N30 Pharmaceuticals, LLC

  公开号：EP2480086A1

  公开（公告）日：2012-08-01
• General Theoretical Treatments of Solid-State Photochemical Rearrangements and a Variety of Contrasting Crystal versus Solution Photochemistry
  作者：Howard E. Zimmerman、Zhaoning Zhu

  DOI：10.1021/ja00124a008

  日期：1995.5

  In continuing our investigations of control of excited state reactivity by inclusion in crystal lattices, we have encountered a variety of new examples of differing reactivity resulting from lattice restraints. Different theoretical treatments were tested and several proved applicable. Not only could the course of reactions imposed by the crystal lattice be predicted but also the ability to react versus lack of reactivity. For cyclohexenones with C-2 and C-5 substitution, either of two aryl groups at C-4 are available for migration; which one migrates depends on the lattice. One C-2 substituted and seven C-5 substituted cyclohexenones were investigated. Additionally some cyclopentenone photochemistry was investigated. Throughout, programming was developed to generate a ''mini crystal lattice'' having the appropriate space group symmetry and X-ray coordinates and with a central molecule surrounded by reactant molecules. Replacement of the central molecule with a transition state molecule provided a new ''mini-lattice''. Generally, the first diradical intermediate was used to simulate the reaction transition state. The mini-lattice was then subject to study. Overlap of the central, partially reacted species with the surrounding molecules provided one criterion. Molecular motion of the reactant excited state in forming the partially reacted species provided a test of least motion as a second criterion. A third test utilizing MM3 geometry optimization of the reacting species imbedded in the rigid mini-lattice, provided a measure of the increase in intra- and intermolecular energy of this molecule. A final approach determined the points of nearest molecule-lattice approach and mapped these in the form of a ''lock and key''; this has the advantage of indicating which interactions result in inhibition or lack thereof of a particular reaction route. Predicting ability to react proved important since reactivity falls into three categories: (I) no reaction in the lattice, (2) differing reactivity compared to solution, (3) the same behavior in solution. Perturbing an intermediate geometry toward that of the reactant and then determining the deformation energy provided a reactivity measure.