exo-5,exo-6-dibromobicyclo[2.2.1]heptane-endo-2,endo-3-diol | 478555-01-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: exo-5,exo-6-dibromobicyclo[2.2.1]heptane-endo-2,endo-3-diol
• 英文别名: (1R,2R,3S,4S,5S,6R)-5,6-dibromobicyclo[2.2.1]heptane-2,3-diol
• CAS: 478555-01-0
• 化学式: C₇H₁₀Br₂O₂
• 分子量: 285.963
• InChiKey: LKOXXTLKTPFBTD-BEOVHNCFSA-N

物化性质

• 熔点：
  126.3 °C
• 沸点：
  332.8±42.0 °C(Predicted)
• 密度：
  2.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  exo-5,exo-6-dibromobicyclo[2.2.1]heptane-endo-2,endo-3-diol 在 potassium tert-butylate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 80.0h， 生成 8-bromo-endo-3,5-dioxatricyclo[5.2.1.0^2,6]dec-8-ene
  参考文献：
  名称：

  Efficient Cyclotrimerization of Bicyclic vic-Bromostannylalkenes Promoted by Copper(I) Thiophen-2-carboxylate

  摘要：

  Copper(I) thiophen-2-carboxylate was successfully employed in the trimerization of [2.2.1] bicyclic vic-bromotrimethyltin olefins (in their racemic composition), bearing different functionalities, to invariably obtain almost quantitative yields of the syn and anti tris-annelated benzenes. The two isomers come in different ratios, smaller than or equal to the statistical 1:3 ratio, depending on the steric hindrance opposed by the functionalities. In the case of enantiopure (3-bromo-4,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl)trimethylstannane, the 1:9 ratio found with Cu(NO3)(2).3H(2)O increases to 1:6.

  DOI：

  10.1021/jo020396s
• 作为产物：
  描述：

  exo-8,exo-9-dibromo-endo-3,5-dioxatricyclo[5.2.1.0^2,6]decan-4-one 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 48.0h， 以97%的产率得到exo-5,exo-6-dibromobicyclo[2.2.1]heptane-endo-2,endo-3-diol
  参考文献：
  名称：

  Efficient Cyclotrimerization of Bicyclic vic-Bromostannylalkenes Promoted by Copper(I) Thiophen-2-carboxylate

  摘要：

  Copper(I) thiophen-2-carboxylate was successfully employed in the trimerization of [2.2.1] bicyclic vic-bromotrimethyltin olefins (in their racemic composition), bearing different functionalities, to invariably obtain almost quantitative yields of the syn and anti tris-annelated benzenes. The two isomers come in different ratios, smaller than or equal to the statistical 1:3 ratio, depending on the steric hindrance opposed by the functionalities. In the case of enantiopure (3-bromo-4,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl)trimethylstannane, the 1:9 ratio found with Cu(NO3)(2).3H(2)O increases to 1:6.

  DOI：

  10.1021/jo020396s