methyl syn-7-chloro-endo-6-iodobicyclo[3.1.1]heptane-exo-6-carboxylate | 1116002-83-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl syn-7-chloro-endo-6-iodobicyclo[3.1.1]heptane-exo-6-carboxylate
• CAS: 1116002-83-5
• 化学式: C₉H₁₂ClIO₂
• 分子量: 314.551
• InChiKey: TVZCPYIQCGVXFT-AQWKKKTISA-N

反应信息

• 作为反应物：
  描述：

  methyl syn-7-chloro-endo-6-iodobicyclo[3.1.1]heptane-exo-6-carboxylate 在 偶氮二异丁腈 、 三苯基氢化锡 作用下， 以 苯 为溶剂， 反应 4.0h， 以75%的产率得到methyl syn-7-chlorobicyclo[3.1.1]heptane-exo-6-carboxylate
  参考文献：
  名称：

  Regio-and stereoselectivity in the halogenation of methyl tricyclo[4.1.0.02,7]heptane-1-carboxylate

  摘要：

  Conjugate halogenation of methyl tricyclo[4.1.0.0(2,7)]heptane-1-carboxylate by the action of N-iodoand N-bromosuccinimides in the presence of halide ions occurs exclusively at the central bicyclobutane C-1-C-7 bond via electrophilic attack on the C-1 atom, leading to endo,syn-adducts of the norpinane series. Reactions of the title compound with iodine, dibromotetrachloroethane, and (dichloro-lambda(3)-iodanyl)benzene give not only the corresponding 6,7-endo,syn-dihalonorpinane but also its epimer at C-6, indicating radical mechanism of the halogenation. The regio-and stereoselectivity observed in these ionic and radical reactions are discussed in terms of the results of nonempirical MP2/STO-3G calculations of appropriate cationic and radical intermediates.

  DOI：

  10.1134/s107042800809008x
• 作为产物：
  描述：

  methyl tricyclo[4.1.0.0(2,7)]heptane-1-carboxylate 在 benzyltriethylammonium chloride iodine chloride 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以45%的产率得到methyl syn-7-chloro-endo-6-iodobicyclo[3.1.1]heptane-exo-6-carboxylate
  参考文献：
  名称：

  Regio-and stereoselectivity in the halogenation of methyl tricyclo[4.1.0.02,7]heptane-1-carboxylate

  摘要：

  Conjugate halogenation of methyl tricyclo[4.1.0.0(2,7)]heptane-1-carboxylate by the action of N-iodoand N-bromosuccinimides in the presence of halide ions occurs exclusively at the central bicyclobutane C-1-C-7 bond via electrophilic attack on the C-1 atom, leading to endo,syn-adducts of the norpinane series. Reactions of the title compound with iodine, dibromotetrachloroethane, and (dichloro-lambda(3)-iodanyl)benzene give not only the corresponding 6,7-endo,syn-dihalonorpinane but also its epimer at C-6, indicating radical mechanism of the halogenation. The regio-and stereoselectivity observed in these ionic and radical reactions are discussed in terms of the results of nonempirical MP2/STO-3G calculations of appropriate cationic and radical intermediates.

  DOI：

  10.1134/s107042800809008x