2-(4-biphenylyl)-2-phenyl-oxirane | 76952-48-2

• 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: 2-(4-biphenylyl)-2-phenyl-oxirane
• 英文别名: 2-Phenyl-2-(4-phenylphenyl)oxirane
• CAS: 76952-48-2
• 化学式: C₂₀H₁₆O
• 分子量: 272.346
• InChiKey: UTGBJBFYMFQEIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  4-苯基二苯甲酮 、 三甲基碘化亚砜 以 氯仿 、 水 、 二甲基亚砜 为溶剂， 生成 2-(4-biphenylyl)-2-phenyl-oxirane
  参考文献：
  名称：

  2-(4-Biphenylyl)-2-(halophenyl)-oxirane compounds

  摘要：

  本发明涉及一种生产具有抗真菌活性的某些羟乙基唑烷的过程，包括在碱金属醇盐和稀释剂的存在下，将选定的苯基取代环氧烷与唑烷反应，优选为咪唑或三唑。本发明还包括选定的苯基取代环氧烷作为新化合物。

  公开号：

  US04480114A1
• 作为试剂：
  描述：

  sodium;hydride 、 三甲基碘化亚砜 、 氢气 、 4-苯基二苯甲酮 、 sodium methylate 、 咪唑 在 氯仿 、 水 、 Sodium sulfate-III 、 2-(4-biphenylyl)-2-phenyl-oxirane 、 乙腈 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲醇 、 水 为溶剂， 反应 6.33h， 以26.7 g (83.5% of theory) of 1-(4-biphenylyl)-2-(imidazol-1-yl)-1-phenyl-ethanol of melting point 224° C. are obtained的产率得到1-(4-biphenylyl)-2-(imidazol-1-yl)-1-phenyl-ethanol
  参考文献：
  名称：

  2-(4-Biphenylyl)-2-(halophenyl)-oxirane compounds

  摘要：

  本发明涉及一种生产具有抗真菌活性的某些羟乙基唑烷的方法，包括在碱金属醇盐和稀释剂的存在下，将选择的苯基取代环氧烷与唑烷，优选咪唑或三唑反应。本发明还包括作为新化合物的选择性苯基取代环氧烷。

  公开号：

  US04480114A1

文献信息

• Verfahren zur Herstellung von Hydroxyethyl-azolen; Zwischenprodukte
  申请人：BAYER AG

  公开号：EP0017080A2

  公开（公告）日：1980-10-15

  Hydroxyethylazole der Formel worin Az Imidazol oder Triazol und R gegebenenfalls substituiertes Phenyl, Naphthyl oder Tetrahydronaphthyl bedeuten, werden nach einem chemisch eigenartigen Verfahren durch Umsetzung von Oxiranen der Formel mit Azolen der Formel in Gegenwart eines Alkalialkoholats und in Gegenwart eines Verdünnungsmittels erhalten. Die Oxirane der Formel II sind zum Teil neu. Dieser Teil ist ebenfalls Gegenstand der Erfindung.

  式中的羟乙基氮唑 其中 Az 是咪唑或三唑，以及 R 是任选取代的苯基、萘基或四氢萘基、 的环氧乙烷与式 与式 在碱金属醇酸酯和稀释剂的存在下进行反应而得到。 其中一些式 II 的环氧乙烷是新型的。 这部分也是本发明的主题。
• US4480114A
  申请人：——

  公开号：US4480114A

  公开（公告）日：1984-10-30
• 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.
• 2-(4-Biphenylyl)-2-(halophenyl)-oxirane compounds
  申请人：Bayer Aktiengesellschaft

  公开号：US04480114A1

  公开（公告）日：1984-10-30

  The invention relates to a process for the production of certain hydroxyethylazoles having antimycotic activity which comprises reacting selected phenyl-substituted oxiranes with azoles, preferably imidazoles or triazoles in the presence of an alkali metal alcoholate and a diluent. Also included in the invention are selected phenyl-substituted oxiranes as novel compounds.

  本发明涉及一种生产具有抗真菌活性的某些羟乙基唑烷的过程，包括在碱金属醇盐和稀释剂的存在下，将选定的苯基取代环氧烷与唑烷反应，优选为咪唑或三唑。本发明还包括选定的苯基取代环氧烷作为新化合物。