exo-6-allyloxy-syn-7-bromo-6-phenylbicyclo[3.1.1]heptane | 956411-67-9

• 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: exo-6-allyloxy-syn-7-bromo-6-phenylbicyclo[3.1.1]heptane
• CAS: 956411-67-9
• 化学式: C₁₆H₁₉BrO
• 分子量: 307.23
• InChiKey: RAXRASYTVWEECK-PLAPLOCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  exo-6-allyloxy-syn-7-bromo-6-phenylbicyclo[3.1.1]heptane 在 sodium hydroxide 、 sodium tetrahydroborate 、 cobaloxime(III) 作用下， 以 乙醇 为溶剂， 以34%的产率得到syn-7-bromo-exo-6-propyloxy-6-phenylbicyclo[3.1.1]heptane
  参考文献：
  名称：

  Synthesis of 3-oxatricyclo[4.4.0.02,7]decene derivatives

  摘要：

  saturated haloethers of norpinane structure were prepared by reaction of N-iodo- and N-bromo-succinimides with 1-phenyltricyclo[4. 1.0.0(2.7)] -heptane in the presence of unsaturated propargyl or allyl alcohol. The iodoproparayloxy derivative underwent reductive 6-exo-cyclization when treated with tributyltin hydride resulting in 5-methylene-3-oxa-2-phenyltricyclo[4.4.0.0(2.7)]decane, and the iodoallyloxy derivative on heating in the presence of benzoyl peroxide suffered isomerization into 5-iodomethyl-3-oxa-2-phenyltricyclo[4.4.0.0(2.7)]decene. Bromopropargyloxy and bromoallyloxy derivatives failed to undergo the reductive cyclization under the treatment with a system cobaloxime(III)-sodium borohydride, but suffered hydrogenetion at the multiple carbon-carbon bond.

  DOI：

  10.1134/s1070428006110078
• 作为产物：
  描述：

  syn-7-bromo-exo-6-propargyloxy-6-phenylbicyclo[3.1.1]heptane 在 sodium hydroxide 、 sodium tetrahydroborate 、 cobaloxime(III) 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以28%的产率得到exo-6-allyloxy-syn-7-bromo-6-phenylbicyclo[3.1.1]heptane
  参考文献：
  名称：

  Synthesis of 3-oxatricyclo[4.4.0.02,7]decene derivatives

  摘要：

  saturated haloethers of norpinane structure were prepared by reaction of N-iodo- and N-bromo-succinimides with 1-phenyltricyclo[4. 1.0.0(2.7)] -heptane in the presence of unsaturated propargyl or allyl alcohol. The iodoproparayloxy derivative underwent reductive 6-exo-cyclization when treated with tributyltin hydride resulting in 5-methylene-3-oxa-2-phenyltricyclo[4.4.0.0(2.7)]decane, and the iodoallyloxy derivative on heating in the presence of benzoyl peroxide suffered isomerization into 5-iodomethyl-3-oxa-2-phenyltricyclo[4.4.0.0(2.7)]decene. Bromopropargyloxy and bromoallyloxy derivatives failed to undergo the reductive cyclization under the treatment with a system cobaloxime(III)-sodium borohydride, but suffered hydrogenetion at the multiple carbon-carbon bond.

  DOI：

  10.1134/s1070428006110078