exo-8,exo-9-dibromo-endo-3,5-dioxatricyclo[5.2.1.0^2,6]decane | 478555-02-1

• 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: exo-8,exo-9-dibromo-endo-3,5-dioxatricyclo[5.2.1.0^2,6]decane
• 英文别名: (1S,2S,6R,7R,8R,9S)-8,9-dibromo-3,5-dioxatricyclo[5.2.1.02,6]decane
• CAS: 478555-02-1
• 化学式: C₈H₁₀Br₂O₂
• 分子量: 297.974
• InChiKey: BZDOTOQHKZXULD-COPVUAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  exo-8,exo-9-dibromo-endo-3,5-dioxatricyclo[5.2.1.0^2,6]decane 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以88%的产率得到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 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 为溶剂， 反应 120.0h， 生成 exo-8,exo-9-dibromo-endo-3,5-dioxatricyclo[5.2.1.0^2,6]decane
  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

文献信息

• Efficient Cyclotrimerization of Bicyclic <i>v</i><i>ic</i>-Bromostannylalkenes Promoted by Copper(I) Thiophen-2-carboxylate
  作者：Giuseppe Borsato、Ottorino De Lucchi、Fabrizio Fabris、Luca Groppo、Vittorio Lucchini、Alfonso Zambon

  DOI：10.1021/jo020396s

  日期：2002.11.1

  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.