2,3,12-trichloropentacyclo<6.4.0.0^2,7.0^3,12.0^4,11>dodeca-5,9-diene-1-carboxylic acid methyl ester | 112185-91-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,12-trichloropentacyclo<6.4.0.0^2,7.0^3,12.0^4,11>dodeca-5,9-diene-1-carboxylic acid methyl ester
• 英文别名: methyl 2,3,12-trichloropentacyclo[6.4.0.02,7.03,12.04,11]dodeca-5,9-diene-1-carboxylate
• CAS: 112185-91-8
• 化学式: C₁₄H₁₁Cl₃O₂
• 分子量: 317.599
• InChiKey: AIJXNJNZZTYWIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3,12-trichloropentacyclo<6.4.0.0^2,7.0^3,12.0^4,11>dodeca-5,9-diene-1-carboxylic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 以100%的产率得到methyl 2,3,12-trichloropentacyclo[6.4.0.02,7.03,12.04,11]dodecane-1-carboxylate
  参考文献：
  名称：

  Synthetic studies towards prismanes: Seco-[6]-prismane

  摘要：

  The first synthesis of seco-[6]-prismane 5, the closest, one-bond-away secologue of [6]-prismane 4, from the readily available Diels-Alder adduct of 1,5-cyclooctadiene and dimethoxytetrachlorocyclopentadiene is described. The key chemical operations in the 17 step sequence are (i) 4+2-cycloaddition of singlet oxygen 20 --> 22, (ii) boron mediated fragmentation 47 --> 14 and (iii) intramolecular 2+2-photocycloaddition 14 --> 49. The methodology outlined here offers opportunities for further elaboration to [6]-prismane as well as several of its homo- and secologues.

  DOI：

  10.1016/s0040-4020(01)81936-0
• 作为产物：
  描述：

  重氮甲烷 、 9,10,12,13-tetrachloropentacyclo<6.5.0.0^4,12.0^5,10.0^9,13>trideca-2,6-dien-11-one 在 sodium hydroxide 作用下， 生成 2,3,12-trichloropentacyclo<6.4.0.0^2,7.0^3,12.0^4,11>dodeca-5,9-diene-1-carboxylic acid methyl ester 、 1,2,3,12-tetrachlorotetracyclo<6.4.0.0^2,7.0^4,11>dodeca-5,9-diene-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthetic studies towards prismanes: Seco-[6]-prismane

  摘要：

  The first synthesis of seco-[6]-prismane 5, the closest, one-bond-away secologue of [6]-prismane 4, from the readily available Diels-Alder adduct of 1,5-cyclooctadiene and dimethoxytetrachlorocyclopentadiene is described. The key chemical operations in the 17 step sequence are (i) 4+2-cycloaddition of singlet oxygen 20 --> 22, (ii) boron mediated fragmentation 47 --> 14 and (iii) intramolecular 2+2-photocycloaddition 14 --> 49. The methodology outlined here offers opportunities for further elaboration to [6]-prismane as well as several of its homo- and secologues.

  DOI：

  10.1016/s0040-4020(01)81936-0