endo,anti,endo-11,12-bis[spiro(cyclopentyl)]-1,2,3,4,4a,5,6,7,8,8a,9a,10a-dodecahydro-1,4:5,8-dimethanoanthracene-9,10-dione | 1352498-55-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: endo,anti,endo-11,12-bis[spiro(cyclopentyl)]-1,2,3,4,4a,5,6,7,8,8a,9a,10a-dodecahydro-1,4:5,8-dimethanoanthracene-9,10-dione
• CAS: 1352498-55-5
• 化学式: C₂₄H₃₂O₂
• 分子量: 352.517
• InChiKey: ODZQHGPQIXWHIX-MRRNPJEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  endo,anti,endo-11,12-bis[spiro(cyclopentyl)]-1,2,3,4,4a,5,6,7,8,8a,9a,10a-dodecahydro-1,4:5,8-dimethanoanthracene-9,10-dione 在 吡啶 、 溴 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 14.17h， 生成 9,10-bis(trifluoromethanesulfonyloxy)-11,12-di[spiro(cyclopentane)]-1,2,3,4,5,6,7,8-octahydro-1,4;5,8-anti-dimethanoanthracene
  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：

  (1S*,4R*,5R*,8S*)-1,4,4a,5,8,8a,9a,10a-octahydro-11,12-di(spirocyclopentane)-1,4:5,8-dimethanoanthracene-9,10-dione 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 48.0h， 以95%的产率得到endo,anti,endo-11,12-bis[spiro(cyclopentyl)]-1,2,3,4,4a,5,6,7,8,8a,9a,10a-dodecahydro-1,4:5,8-dimethanoanthracene-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.