methyl exo-6,syn-7-dinitro-exo-6-phenylsulfonylbicyclo[3.1.1]heptane | 1047637-82-0

• 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: methyl exo-6,syn-7-dinitro-exo-6-phenylsulfonylbicyclo[3.1.1]heptane
• CAS: 1047637-82-0
• 化学式: C₁₃H₁₄N₂O₆S
• 分子量: 326.33
• InChiKey: KBWSRDXLTFOOST-PPANGVADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  120.42
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  1-(phenylsulfonyl)tricyclo<4.1.0.0^2,7>heptane 在 dinitrogen tetraoxide 、 甲醇 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以32%的产率得到methyl exo-6,syn-7-dinitro-endo-6-phenylsulfonylbicyclo[3.1.1]heptane
  参考文献：
  名称：

  Reaction products of methyl tricyclo[4.1.0.02,7]heptane-1-carboxylate and tricyclo[4.1.0.02,7]hept-1-yl phenyl sulfone with dinitrogen tetraoxide

  摘要：

  The reaction of methyl tricyclo[4.1.0.0(2,7)]heptane-l-carboxylate with dinitrogen tetraoxide in diethyl ether at -10 to 0 degrees C, followed by treatment of the reaction mixture with methanol, gave approximately equal amounts of methyl exo,syn-6,7-dinitro- and exo-6-hydroxy-syn-7-nitrobicyclo[3.1.1]heptane-endo-6-carboxylates. Tricyclo[4.1.0.0(2,7)]hept-1-yl phenyl sulfone reacted with dinitrogen tetraoxide under analogous conditions to produce a mixture of diastereoisomeric exo,syn- and endo,syn-6,7-dinitro-6-phenylsulfonylbicyclo[3.1.1]heptanes and 6,6-dimethoxy-endo-7-nitrobicyclo[3.1.1]heptane at a ratio of 4.5: 2: 1. Probable factors responsible for the different stereoselectivities in the addition of N(2)O(4) at the central C(1)-C(7) bond of the initial tricycloheptane Compounds were discussed. The structural parameters of the dinitro ester and related dinitro sulfone were compared on the basis of the X-ray diffraction data.

  DOI：

  10.1134/s1070428008040076