12-oxahexacyclo<7.2.1.0^2,8.0^3,7.0^4,11.0^6,11>dodecane-1-malonic acid | 147661-31-2

• 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: 12-oxahexacyclo<7.2.1.0^2,8.0^3,7.0^4,11.0^6,11>dodecane-1-malonic acid
• 英文别名: 2-(5-Oxahexacyclo[5.4.1.02,6.03,10.04,8.09,12]dodecan-4-yl)propanedioic acid
• CAS: 147661-31-2
• 化学式: C₁₄H₁₄O₅
• 分子量: 262.262
• InChiKey: VXJITYZPWSVVEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  12-oxahexacyclo<7.2.1.0^2,8.0^3,7.0^4,11.0^6,11>dodecane-1-malonic acid 在 氯化亚砜 作用下， 反应 2.0h， 生成 ethyl 12-oxahexacyclo<7.2.1.0^2,8.0^3,7.0^4,11.0^6,11>dodecane-1-acetate
  参考文献：
  名称：

  Synthesis of 1-substituted 12-oxahexacyclo[7.2.1.02,8.03,7.04,11.06,10]dodecanes and their transformation into pentacyclo[6.3.0.02,6.03,10.05,9]undecane derivatives

  摘要：

  The reaction of nucleophilic reagents (organomagnesium and organosodium compounds containing active methylene groups) with exo-11-bromopentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecan-8-one leads to the formation of 1-substituted-12-oxahexacyclo[7.2.1.0(2,8).0(3,7).0(4,11).0(6,10)] dodecanes which can be used in the synthesis of trishomocubane derivatives. It is shown, using the 1-methyl- and 1-phenyl-substituted 12-oxadodecanes, that iodotrimethylsilane readily cleaves the ether bond at C(l). The resulting carbonium ions rearrange to form 1,7,11-trisubstituted pentacyclo[6.3.0.0(2,6).0(3,10).0(5,9)]-undecanes.

  DOI：

  10.1021/jo00059a039
• 作为产物：
  描述：

  exo-11-bromopentacyclo<5.4.0.0^2,6.0^3,10.0^5,9>undecane-8-one 在 氢氧化钾 、 乙醇 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 60.0h， 生成 12-oxahexacyclo<7.2.1.0^2,8.0^3,7.0^4,11.0^6,11>dodecane-1-malonic acid
  参考文献：
  名称：

  Synthesis of 1-substituted 12-oxahexacyclo[7.2.1.02,8.03,7.04,11.06,10]dodecanes and their transformation into pentacyclo[6.3.0.02,6.03,10.05,9]undecane derivatives

  摘要：

  The reaction of nucleophilic reagents (organomagnesium and organosodium compounds containing active methylene groups) with exo-11-bromopentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecan-8-one leads to the formation of 1-substituted-12-oxahexacyclo[7.2.1.0(2,8).0(3,7).0(4,11).0(6,10)] dodecanes which can be used in the synthesis of trishomocubane derivatives. It is shown, using the 1-methyl- and 1-phenyl-substituted 12-oxadodecanes, that iodotrimethylsilane readily cleaves the ether bond at C(l). The resulting carbonium ions rearrange to form 1,7,11-trisubstituted pentacyclo[6.3.0.0(2,6).0(3,10).0(5,9)]-undecanes.

  DOI：

  10.1021/jo00059a039

文献信息

• Synthesis of 1-substituted 12-oxahexacyclo[7.2.1.02,8.03,7.04,11.06,10]dodecanes and their transformation into pentacyclo[6.3.0.02,6.03,10.05,9]undecane derivatives
  作者：Alexander M. Aleksandrov、Ram P. Kashyap、Tynis J. Pehk、Alexander E. Petrenko、William H. Watson

  DOI：10.1021/jo00059a039

  日期：1993.3

  The reaction of nucleophilic reagents (organomagnesium and organosodium compounds containing active methylene groups) with exo-11-bromopentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecan-8-one leads to the formation of 1-substituted-12-oxahexacyclo[7.2.1.0(2,8).0(3,7).0(4,11).0(6,10)] dodecanes which can be used in the synthesis of trishomocubane derivatives. It is shown, using the 1-methyl- and 1-phenyl-substituted 12-oxadodecanes, that iodotrimethylsilane readily cleaves the ether bond at C(l). The resulting carbonium ions rearrange to form 1,7,11-trisubstituted pentacyclo[6.3.0.0(2,6).0(3,10).0(5,9)]-undecanes.