(+/-)-(1R*,2R*,3S*,6R*,7S*,8S*)-1,8,9,10-Tetrachlor-11,11-dimethoxytricyclo<6.2.1.0^2.7>-undec-9-en-3,6-diol | 157768-98-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-(1R*,2R*,3S*,6R*,7S*,8S*)-1,8,9,10-Tetrachlor-11,11-dimethoxytricyclo<6.2.1.0^2.7>-undec-9-en-3,6-diol
• 英文别名: (1R,2R,3S,6R,7S,8S)-1,8,9,10-tetrachloro-11,11-dimethoxytricyclo[6.2.1.02,7]undec-9-ene-3,6-diol
• CAS: 157768-98-4
• 化学式: C₁₃H₁₆Cl₄O₄
• 分子量: 378.08
• InChiKey: UYUMRQNLUKPSBK-OCYKKEQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  (+/-)-(1R*,2R*,3S*,6R*,7S*,8S*)-1,8,9,10-Tetrachlor-11,11-dimethoxytricyclo<6.2.1.0^2.7>-undec-9-en-3,6-diol 在 sodium ethanolate 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (+/-)-(1S*,3R*,5R*,7R*,8S*,9R*,10R*)-10-Benzyloxy-3-ethoxy-6,6-dimethoxy-2-oxatetracyclo<6.4.0.0^3.7.0^5.9>dodecan
  参考文献：
  名称：

  Synthese des all-cis-Perhydronaphtho[1,8-bc]furansystems durch Photocyclisierung

  摘要：

  The diketone 3 was reduced to the diol which then was transformed to the tetracyclic diketal 5 by treatment with sodium in ethanol. Protection of the remaining hydroxy group was followed by hydrolysis of the dimethylketal. The resulting ketone 7 was stereoselectively converted to the tertiary alcohol by methyl magnesium chloride. Acidic retrograde aldol reaction of the tertiary alcohol led to the decalindione 10, which was partially dehydrogenated by cupric chloride under basic conditions. The resulting endione 1 cyclized by light induced hydrogen abstraction and collapse of the resulting diradical to the perhydronaphtho[1,8-bc]furan derivative.

  DOI：

  10.1007/bf01277639
• 作为产物：
  描述：

  1,2,3,4-Tetrachloro-9,9-dimethoxy-1α,4α,4aα,6,7,8aα-hexahydro-1,4-methanonaphthalene-5,8-dione 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (+/-)-(1R*,2R*,3S*,6R*,7S*,8S*)-1,8,9,10-Tetrachlor-11,11-dimethoxytricyclo<6.2.1.0^2.7>-undec-9-en-3,6-diol
  参考文献：
  名称：

  Synthese des all-cis-Perhydronaphtho[1,8-bc]furansystems durch Photocyclisierung

  摘要：

  The diketone 3 was reduced to the diol which then was transformed to the tetracyclic diketal 5 by treatment with sodium in ethanol. Protection of the remaining hydroxy group was followed by hydrolysis of the dimethylketal. The resulting ketone 7 was stereoselectively converted to the tertiary alcohol by methyl magnesium chloride. Acidic retrograde aldol reaction of the tertiary alcohol led to the decalindione 10, which was partially dehydrogenated by cupric chloride under basic conditions. The resulting endione 1 cyclized by light induced hydrogen abstraction and collapse of the resulting diradical to the perhydronaphtho[1,8-bc]furan derivative.

  DOI：

  10.1007/bf01277639

文献信息

• Goessinger E., Graupe M., Zimmermann K., Monatsh. Chem, 125 (1994) N 6-7, S 773-782
  作者：Goessinger E., Graupe M., Zimmermann K.

  DOI：——

  日期：——
• Synthese des all-cis-Perhydronaphtho[1,8-bc]furansystems durch Photocyclisierung
  作者：E. G�ssinger、M. Graupe、K. Zimmermann

  DOI：10.1007/bf01277639

  日期：1994.6

  The diketone 3 was reduced to the diol which then was transformed to the tetracyclic diketal 5 by treatment with sodium in ethanol. Protection of the remaining hydroxy group was followed by hydrolysis of the dimethylketal. The resulting ketone 7 was stereoselectively converted to the tertiary alcohol by methyl magnesium chloride. Acidic retrograde aldol reaction of the tertiary alcohol led to the decalindione 10, which was partially dehydrogenated by cupric chloride under basic conditions. The resulting endione 1 cyclized by light induced hydrogen abstraction and collapse of the resulting diradical to the perhydronaphtho[1,8-bc]furan derivative.