(1α,4α,4aβ,5β,8β,8aβ)-1,2,3,4-tetrachloro-1,4,4a,5,8,8a-hexahydro-9,9-dimethoxy-1,4-methanonaphthalene-5,8-diol | 146565-73-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1α,4α,4aβ,5β,8β,8aβ)-1,2,3,4-tetrachloro-1,4,4a,5,8,8a-hexahydro-9,9-dimethoxy-1,4-methanonaphthalene-5,8-diol
• 英文别名: (1β,4β,4aβ,5α,8α,8aβ)-5,6,7,8-tetrachloro-1,4,4a,5,8,8a-hexahydro-9,9-dimethoxy-5,8-methanonaphthalene-1,4-diol；(1R,2R,3R,6S,7S,8S)-1,8,9,10-tetrachloro-11,11-dimethoxytricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-diol
• CAS: 146565-73-3
• 化学式: C₁₃H₁₄Cl₄O₄
• 分子量: 376.064
• InChiKey: PRHREUALBBVUMW-IRHARMPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1α,4α,4aβ,5β,8β,8aβ)-1,2,3,4-tetrachloro-1,4,4a,5,8,8a-hexahydro-9,9-dimethoxy-1,4-methanonaphthalene-5,8-diol 在 jones reagent 、 氨 、 sodium 、 calcium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 102.67h， 生成 (1α,4α,4aβ,5α,8α,8aβ,9aβ,10aβ)-1,4,4a,5,8,8a,9,9a,10,10a-decahydro-11,11,12,12-tetramethoxy-4a,8a-dimethyl-1,4:5,8-dimethanoanthracene-9,10-dione
  参考文献：
  名称：

  Convenient synthesis of the 1,4-bishomo-6-secoheptaprismane ring system

  摘要：

  The facile synthesis of 13, a highly functionalized 1,4-bishomo-6-secoheptaprismane, is reported in 45% overall yield, starting with the Diels-Alder adduct of 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopentadiene and p-benzoquinone. Initial attempts to functionalize 13 for subsequent transformation to hexaprismane (1) are summarized.

  DOI：

  10.1021/jo00058a035
• 作为产物：
  描述：

  [(1S,2S,3R,6S,7R,8R)-1,8,9,10-tetrachloro-11,11-dimethoxy-6-methylsulfonyloxy-3-tricyclo[6.2.1.02,7]undeca-4,9-dienyl] methanesulfonate 在 氧气 、 tetraphenylporphyrin 、 溶剂黄146 、 sodium iodide 、 锌 作用下， 以 四氯化碳 、 丁酮 为溶剂， 反应 3.5h， 生成 (1α,4α,4aβ,5β,8β,8aβ)-1,2,3,4-tetrachloro-1,4,4a,5,8,8a-hexahydro-9,9-dimethoxy-1,4-methanonaphthalene-5,8-diol
  参考文献：
  名称：

  Convenient synthesis of the 1,4-bishomo-6-secoheptaprismane ring system

  摘要：

  The facile synthesis of 13, a highly functionalized 1,4-bishomo-6-secoheptaprismane, is reported in 45% overall yield, starting with the Diels-Alder adduct of 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopentadiene and p-benzoquinone. Initial attempts to functionalize 13 for subsequent transformation to hexaprismane (1) are summarized.

  DOI：

  10.1021/jo00058a035

文献信息

• Synthesis of<i>Endo,Endo</i>-2.9-Dihydroxypentacyclo-[8.4.0.0^3,8.0^4,14.0^7,11]Tetradeca-5,12-Diene
  作者：Teh-Chang Chou、Gerng-Horng Lin、Sen-Ching Wu、Sushilkumar S. Bahekar

  DOI：10.1002/jccs.200800026

  日期：2008.2

  The title compound 30 was synthesized starting from the endo,syn,endo Diels-Alder adduct 3a of hexahydro-5,6,7,8-tetrachloro-9,9-dimethoxy-5,8-methanonaphthalene-1,4-diol diacetate 6 and 1,2,3,4-tetrachloro-5,5-dimethoxycyclopentadiene (TDCp) in six steps, keyed upon a symmetry-allowed [4+4] photocyclization of decahydro-11,12-dioxo-[1,4;5,8]dimethanoanthracene-9,10-diol diacetate 22. The epimeric

  标题化合物 30 由 hexahydro-5,6,7,8-tetrachlor-9,9-dimethoxy-5,8-methannaphthalene-1,4-diol diacetate 的 endo,syn,endo Diels-Alder 加合物 3a 合成6 和 1,2,3,4-四氯-5,5-二甲氧基环戊二烯 (TDCp) 分六个步骤，关键是十氢-11,12-二氧代-[1,4] 的对称允许 [4+4] 光环化； 5,8]dimethanoanthracene-9,10-diol diacetate 22。还合成了与22相关的差向异构单乙酸26，并研究了它们的热解和光解作用。由于跨环反应，二醇 30 的氧化得到六环桥接半缩醛 31。通过单晶X射线晶体学分析半缩醛31的结构。
• Facile stereoselective reductions of enediones and cage diketones suing sodium borohydride-cerium(III) chloride
  作者：Alan P. Marchand、William D. LaRoe、G. V. Madhava Sharma、Suresh Chander Suri、D. Sivakumar Reddy

  DOI：10.1021/jo00359a054

  日期：1986.5
• Convenient synthesis of the 1,4-bishomo-6-secoheptaprismane ring system
  作者：Mark A. Forman、William P. Dailey

  DOI：10.1021/jo00058a035

  日期：1993.3

  The facile synthesis of 13, a highly functionalized 1,4-bishomo-6-secoheptaprismane, is reported in 45% overall yield, starting with the Diels-Alder adduct of 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopentadiene and p-benzoquinone. Initial attempts to functionalize 13 for subsequent transformation to hexaprismane (1) are summarized.