| 195386-30-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• CAS: 195386-30-2
• 化学式: C₂₀H₂₈F₂N₂S
• 分子量: 366.519
• InChiKey: VNMWRHJRTMKJDO-UHFFFAOYSA-N

物化性质

• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  25.0
• 可旋转键数：
  0.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  24.06
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  在 lead(IV) acetate 作用下， 生成
  参考文献：
  名称：

  σ,π Interaction in Halogen-Substituted Biadamantylidene Radical Cations

  摘要：

  The order of E degrees' and vIP for 4-eq-halogenated-biadamantylidene is F > Cl congruent to Br, and the 5-F-substituted compound is harder to ozidize than the 4-eq-F-substituted one. The former result is most consistent with a detectable resonance contribution through the sigma-framework, and the latter with sigma-hyperconjugative destablilization proceeding through two pathways being more than double the same effect through one pathway (the Whiffen effect). AM1 calculations predict these results. The facial selectivity for epoxidation and diazetidine formation from 4-eq-halogenated 3 (4(X)) is in the order Cl > F > Br, and the 5-fluoro compound (8) is less selective than 4(F) for both reactions. Steric as well as electronic factors might well contribute to these results, neither of which was expected from consideration of sigma,pi interaction. Cation radical catalyzed chain dioxetane formation from 4(F) and 3(Cl) is significantly more face selective than epoxidation or diazetidine formation,as expected on electronic grounds; sigma,pi interaction should be larger in the radical cation.

  DOI：

  10.1021/jo970252r
• 作为产物：
  描述：

  5-fluoroadamantan-2-one azine 在 硫化氢 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成
  参考文献：
  名称：

  σ,π Interaction in Halogen-Substituted Biadamantylidene Radical Cations

  摘要：

  The order of E degrees' and vIP for 4-eq-halogenated-biadamantylidene is F > Cl congruent to Br, and the 5-F-substituted compound is harder to ozidize than the 4-eq-F-substituted one. The former result is most consistent with a detectable resonance contribution through the sigma-framework, and the latter with sigma-hyperconjugative destablilization proceeding through two pathways being more than double the same effect through one pathway (the Whiffen effect). AM1 calculations predict these results. The facial selectivity for epoxidation and diazetidine formation from 4-eq-halogenated 3 (4(X)) is in the order Cl > F > Br, and the 5-fluoro compound (8) is less selective than 4(F) for both reactions. Steric as well as electronic factors might well contribute to these results, neither of which was expected from consideration of sigma,pi interaction. Cation radical catalyzed chain dioxetane formation from 4(F) and 3(Cl) is significantly more face selective than epoxidation or diazetidine formation,as expected on electronic grounds; sigma,pi interaction should be larger in the radical cation.

  DOI：

  10.1021/jo970252r