endo-11,11-dimethoxy-1,4,4a,9a-tetrahydro-1,4-methanoanthracene-9,10-dione | 1352498-64-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: endo-11,11-dimethoxy-1,4,4a,9a-tetrahydro-1,4-methanoanthracene-9,10-dione
• 英文别名: (1S,2S,11R,12R)-15,15-dimethoxytetracyclo[10.2.1.02,11.04,9]pentadeca-4,6,8,13-tetraene-3,10-dione
• CAS: 1352498-64-6
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: JAEVWWCHPRTBEU-LVEBTZEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  endo-11,11-dimethoxy-1,4,4a,9a-tetrahydro-1,4-methanoanthracene-9,10-dione 在 甲酸 、 1,1'-bis(diphenylphosphino)ferrocene 、 palladium diacetate 、 双(三甲基硅烷基)氨基钾 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 11,11-dimethoxy-1,2,3,4-tetrahydro-1,4-methanoanthracene
  参考文献：
  名称：

  Deoxygenation of Hydroquinones as a General Route to Norbornane-Fused Aromatic Systems: An Entry into Substituted and Functionalized Dimethano- and Methanoanthracenes

  摘要：

  A high-yielding route to substituted and functionalized dimethanoanthracenes by the Pd-catalyzed deoxyenation of the corresponding hydroquinone precursors is described. Attempts were made to deoxygenate the 9,10-dimesylate, ditosylate, and ditriflate derivatives of anti-dimethanoanthracene la, and it was found that under the studied conditions only the ditriflate 8a gave the corresponding deoxygenated aromatic scaffold. Optimization of the reaction conditions identified the Pd(OAc)(2)/dppf tandem as a suitable catalytic system for this transformation. The presented strategy was further extended to a novel and efficient synthetic route to methanoanthracenes employing a one-pot Pd-catalyzed deoxygenation/hydrogenation sequence.

  DOI：

  10.1021/jo202023w
• 作为产物：
  描述：

  5,5-dimethoxycyclopenta-1,3-diene 、 1,4-萘醌 以 二氯甲烷 为溶剂， 反应 12.0h， 以65%的产率得到endo-11,11-dimethoxy-1,4,4a,9a-tetrahydro-1,4-methanoanthracene-9,10-dione
  参考文献：
  名称：

  Deoxygenation of Hydroquinones as a General Route to Norbornane-Fused Aromatic Systems: An Entry into Substituted and Functionalized Dimethano- and Methanoanthracenes

  摘要：

  A high-yielding route to substituted and functionalized dimethanoanthracenes by the Pd-catalyzed deoxyenation of the corresponding hydroquinone precursors is described. Attempts were made to deoxygenate the 9,10-dimesylate, ditosylate, and ditriflate derivatives of anti-dimethanoanthracene la, and it was found that under the studied conditions only the ditriflate 8a gave the corresponding deoxygenated aromatic scaffold. Optimization of the reaction conditions identified the Pd(OAc)(2)/dppf tandem as a suitable catalytic system for this transformation. The presented strategy was further extended to a novel and efficient synthetic route to methanoanthracenes employing a one-pot Pd-catalyzed deoxygenation/hydrogenation sequence.

  DOI：

  10.1021/jo202023w

文献信息

• Deoxygenation of Hydroquinones as a General Route to Norbornane-Fused Aromatic Systems: An Entry into Substituted and Functionalized Dimethano- and Methanoanthracenes
  作者：Prasad Ganji、Hasim Ibrahim

  DOI：10.1021/jo202023w

  日期：2012.1.6

  A high-yielding route to substituted and functionalized dimethanoanthracenes by the Pd-catalyzed deoxyenation of the corresponding hydroquinone precursors is described. Attempts were made to deoxygenate the 9,10-dimesylate, ditosylate, and ditriflate derivatives of anti-dimethanoanthracene la, and it was found that under the studied conditions only the ditriflate 8a gave the corresponding deoxygenated aromatic scaffold. Optimization of the reaction conditions identified the Pd(OAc)(2)/dppf tandem as a suitable catalytic system for this transformation. The presented strategy was further extended to a novel and efficient synthetic route to methanoanthracenes employing a one-pot Pd-catalyzed deoxygenation/hydrogenation sequence.