4,5,6,7-tetrachloro-14,14-dimethoxy-13-oxatetracyclo<8.2.1.14,7.03,8>tetradec-5,11-dien-1-ol | 138738-73-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,5,6,7-tetrachloro-14,14-dimethoxy-13-oxatetracyclo<8.2.1.14,7.03,8>tetradec-5,11-dien-1-ol
• 英文别名: 4,5,6,7-tetrachloro-14,14-dimethoxy-13-oxatetracyclo<8.2.1.1^4,7.0^3,8>tetradec-5,11-dien-1-ol
• CAS: 138738-73-5
• 化学式: C₁₅H₁₆Cl₄O₄
• 分子量: 402.102
• InChiKey: LHCNCTUESZZTTP-YOZAFYTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4,5,6,7-tetrachloro-14,14-dimethoxy-13-oxatetracyclo<8.2.1.14,7.03,8>tetradec-5,11-dien-1-ol 在 jones reagent 作用下， 以 丙酮 为溶剂， 以68%的产率得到rac-(3bR,4S,7R,7aS)-4,5,6,7-tetrachloro-8a-hydroxy-9,9-dimethoxy-3b,4,7,7a,8,8a-hexahydro-4,7-methanocyclopenta[a]inden-3(3aH)-one
  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：

  1,10,11,12-tetrachloro-13,13-dimethoxytricyclo<8.2.1.0^2,9>-trideca-5,11-diene 在 亚甲兰 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 氧气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 172.0h， 生成 4,5,6,7-tetrachloro-14,14-dimethoxy-13-oxatetracyclo<8.2.1.14,7.03,8>tetradec-5,11-dien-1-ol
  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