11,12-bis[spiro(cyclopentyl)]-1,2,3,4,5,6,7,8-octahydro-1:4,5:8-anti-dimethanoanthracene | 195301-12-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 11,12-bis[spiro(cyclopentyl)]-1,2,3,4,5,6,7,8-octahydro-1:4,5:8-anti-dimethanoanthracene
• CAS: 195301-12-3
• 化学式: C₂₄H₃₀
• 分子量: 318.502
• InChiKey: DPYKQKFCSXGTEK-COPRSSIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.76
• 重原子数：
  24.0
• 可旋转键数：
  0.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  11,12-bis[spiro(cyclopentyl)]-1,2,3,4,5,6,7,8-octahydro-1:4,5:8-anti-dimethanoanthracene 在 硫酸 、 4-甲基苯磺酸吡啶 、 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 22.0h， 生成 (+)-(1S,4R,5R,8S)-1,2,3,4,5,6,7,8-octahydro-11,12-di(spirocyclopentane)-1,4:5,8-dimethanoanthracene-9-carboxaldehyde
  参考文献：
  名称：

  Synthesis and catalytic reactivity of sterically and electronically modified D4-symmetric metallotetraarylporphyrins

  摘要：

  Two new sterically-modified and two electronically-modified D-4-symmetrical tetraarylporphyrin ligands have been prepared and the catalytic activity of their manganese complexes in epoxidations of aryl-substituted alkenes studied. Moderate reactivity changes were observed in catalytic epoxdiations with these electronically varied tetraaarylporphyrin complexes, the methoxy derivative giving slightly improved selectivity (83% e.e. with cis-beta-methylstyrene). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00730-8
• 作为产物：
  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 、 甲酸 、 1,1'-bis(diphenylphosphino)ferrocene 、 溴 、 palladium diacetate 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.17h， 生成 11,12-bis[spiro(cyclopentyl)]-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

文献信息

• Synthesis and catalytic reactivity of sterically and electronically modified D4-symmetric metallotetraarylporphyrins
  作者：Ronald L. Halterman、Shyi-Tai Jan、Aladamash H. Abdulwali、David J. Standlee

  DOI：10.1016/s0040-4020(97)00730-8

  日期：1997.8

  Two new sterically-modified and two electronically-modified D-4-symmetrical tetraarylporphyrin ligands have been prepared and the catalytic activity of their manganese complexes in epoxidations of aryl-substituted alkenes studied. Moderate reactivity changes were observed in catalytic epoxdiations with these electronically varied tetraaarylporphyrin complexes, the methoxy derivative giving slightly improved selectivity (83% e.e. with cis-beta-methylstyrene). (C) 1997 Elsevier Science Ltd.
• 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.