(1R,4S,4aR,5R,8S,8aS)-6,7-bis(phenylsulfonyl)-10-(propan-2-ylidene)-1,2,3,4,5,8-hexahydro-1,4:4a,8a:5,8-trimethanonaphthalene | 166805-43-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (1R,4S,4aR,5R,8S,8aS)-6,7-bis(phenylsulfonyl)-10-(propan-2-ylidene)-1,2,3,4,5,8-hexahydro-1,4:4a,8a:5,8-trimethanonaphthalene
• CAS: 166805-43-2
• 化学式: C₂₈H₂₈O₄S₂
• 分子量: 492.66
• InChiKey: ZGRBXWYKTJIKQV-FMWZGFPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.55
• 重原子数：
  34.0
• 可旋转键数：
  4.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  68.28
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,4S,4aR,5R,8S,8aS)-6,7-bis(phenylsulfonyl)-10-(propan-2-ylidene)-1,2,3,4,5,8-hexahydro-1,4:4a,8a:5,8-trimethanonaphthalene 以 various solvent(s) 为溶剂， 生成 (1R,2R,3S,4S,4aS,5S,8R,8aR)-2,3-bis(phenylsulfonyl)-11-(propan-2-ylidene)-1,2,3,4,5,8-hexahydro-1,4:4a,8a:5,8-trimethanonaphthalene
  参考文献：
  名称：

  Paquette, Leo A.; O'Doherty, George A.; Rogers, Robin D., Journal of the American Chemical Society, 1991, vol. 113, # 20, p. 7761 - 7762

  摘要：

  DOI：
• 作为产物：
  描述：

  (1R,3R,6S,8S,9S,10R)-9,10-bis(benzenesulfonyl)-11-propan-2-ylidenetetracyclo[6.2.1.13,6.02,7]dodeca-2(7),4-diene 以 various solvent(s) 为溶剂， 反应 0.75h， 生成 (1R,4S,4aR,5R,8S,8aS)-6,7-bis(phenylsulfonyl)-10-(propan-2-ylidene)-1,2,3,4,5,8-hexahydro-1,4:4a,8a:5,8-trimethanonaphthalene
  参考文献：
  名称：

  Consequences of Modulated Precompression along Reaction Coordinates. Synthesis, Crystallographic Structural Studies, and Rate of Intramolecular Dyotropy in an Extended Series of syn-Sesquinorbornene Disulfones

  摘要：

  In order to produce a broad range of syn-sesquinorbornene disulfones, (Z)-1,2-bis(phenylsulfonyI)ethylene was added in Diels-Alder fashion (high-pressure conditions) to tricyclo[5.2.1.0(2.6)]deca-2,5,8-trienes carrying isopropylidene or spirocyclopropane subunits at one or two sites. The central double bond in these adducts was then regiospecifically reduced with diimide, epoxidized with MCPBA, or cyclopropanated by [3 + 2] cycloaddition with diazomethane and subsequent photoinduced nitrogen extrusion. Each product in ah-three series was subjected to X-ray crystallographic analysis in order to quantify in the solid state the distance which each endo alpha-sulfonyl proton is required to traverse during dyotropic migration to the proximal norbornene double bond. The kinetics of these isomerizations were also determined, a relative reactivity scale was realized, and the values of k(ref) at 160 degrees C were found not to correlate well with the average distance across the intracavity gap. Although proximity of the reaction centers is clearly a prerequisite for smooth operation of the dyotropic shifts, modulation of this distance is not the sole contributor to reaction rate. Rather, the data are in agreement with the working hypothesis that various levels of steric compression within these disulfones facilitate passage over the relevant transition state to a greater or lesser degree depending on the magnitude of these nonbonded interactions.

  DOI：

  10.1021/ja00103a004