spiro <9-hydro-10-oxo-phenanthrene-9-oxirane> | 22219-64-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: spiro <9-hydro-10-oxo-phenanthrene-9-oxirane>
• 英文别名: 10,10¹-Oxido-10-methyl-phenanthron-(9)；9,9¹-Oxido-9-methyl-phenanthron；spiro[oxirane-2,9'-phenanthren]-10'-one；Spiro(oxiran-2,9'-phenanthren)-10'-on；Spiro[oxirane-2,10'-phenanthrene]-9'-one
• CAS: 22219-64-3
• 化学式: C₁₅H₁₀O₂
• 分子量: 222.243
• InChiKey: UXHJTVLONHFUDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  spiro <9-hydro-10-oxo-phenanthrene-9-oxirane> 在 三氟化硼乙醚 作用下， 生成 10-difluoroboranyloxy-phenanthrene-9-carbaldehyde
  参考文献：
  名称：

  Eistert et al., Chemische Berichte, 1958, vol. 91, p. 2710,2717

  摘要：

  DOI：
• 作为产物：
  描述：

  重氮甲烷 、 菲醌 以 乙醚 为溶剂， 以53%的产率得到spiro <9-hydro-10-oxo-phenanthrene-9-oxirane>
  参考文献：
  名称：

  Homologation of Vicinal Polyketone Networks to Epoxy Ketones with Diazomethane

  摘要：

  DOI：

  10.3987/com-04-s(p)9

文献信息

• Arndt; Amende; Ender, Monatshefte fur Chemie, 1932, vol. 59, p. 213
  作者：Arndt、Amende、Ender

  DOI：——

  日期：——
• Tautomerism of representative aromatic α-hydroxy carbaldehyde anils as studied by spectroscopic methods and AM1 calculations. Synthesis of 10-hydroxyphenanthrene-9-carbaldehyde
  作者：Sergio H. Alarcón、Alejandro C. Olivieri、Guillermo R. Labadie、Raquel M. Cravero、Manuel González-Sierra

  DOI：10.1016/0040-4020(95)00002-p

  日期：1995.4

  The synthesis of 10-hydroxyphenanthrene-9-carbaldehyde and its anil are described. The structure of the latter compound has been thoroughly studied by H-1 and C-13 NMR, UV-visible absorption, fluorescence and IR spectroscopies. All the experimental results support the existence of this anil mainly in the keto-enamine tautomeric form. A comparison is presented with previously studied anils derived from salicylaldehyde and 2-hydroxynaphthalene-1-carbaldehyde. Semiempirical calculations (AM1) concerning the relative stability of tautomers as well as the optimized molecular geometries are in good agreement with the experimental findings.