((6R,11R,12S)-8,9-dimethoxy-11,12-dihydro-6H-6,12-methanodibenzo[b,f]oxocin-11-yl)(phenyl)methanone | 1447951-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((6R,11R,12S)-8,9-dimethoxy-11,12-dihydro-6H-6,12-methanodibenzo[b,f]oxocin-11-yl)(phenyl)methanone
• CAS: 1447951-83-8
• 化学式: C₂₅H₂₂O₄
• 分子量: 386.447
• InChiKey: SHUXFGOJRXFDFE-MEKIYTOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  乙酰苯 、 4,5-dimethoxy-2-(2-phenylethynyl)benzaldehyde 在 (11bS)-4-羟基-2,6-二[2,4,6-三(异丙基)苯基]-二萘并[2,1-d:1',2'-f][1,3,2]二氧杂磷杂卓4-氧化物 、 palladium diacetate 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到((6R,11R,12S)-8,9-dimethoxy-11,12-dihydro-6H-6,12-methanodibenzo[b,f]oxocin-11-yl)(phenyl)methanone
  参考文献：
  名称：

  Asymmetric Cascade Annulation Based on Enantioselective Oxa-Diels–Alder Cycloaddition of in Situ Generated Isochromenyliums by Cooperative Binary Catalysis of Pd(OAc)₂ and (S)-Trip

  摘要：

  An asymmetric cascade annulation between 2-hydroxystyrenes and 2-alkynylbenaldehyes or 1-(2-alkynylphenyl)ketones has been established with good to excellent enantioselectivities (up to >99.5% ee), on the basis of an enantioselective oxa-Diels-Alder cycloaddition of in situ generated metallo-isochromenylium intermediates, by cooperative binary catalysis of Pd(OAc)(2) and (S)-Trip. The developed methodology is workable for a broad spectrum of substrates and shows great efficiency in establishing dense multiple chiral centers including quaternary carbons of variable bridged ring systems. The mechanism study suggests that (S)-Trip plays multiple roles in assembling the reactants and controlling the stereoselectivity.

  DOI：

  10.1021/ja405764p

文献信息

• Construction of Multiring Frameworks by Metal-Free Cascade Reactions of Stable Isochromenylium Tetrafluoroborate
  作者：Zhi-Long Hu、Wen-Jian Qian、Sheng Wang、Shaozhong Wang、Zhu-Jun Yao

  DOI：10.1021/jo902051g

  日期：2009.11.20

  Efficient methodologies for constructing several multiring frameworks have been developed utilizing the cascade reactions of air-stable isochromenylium tetrafluoroborates with olefins. Successive additions of two equivalents of styrene-type olefins to isochromenylium tetrafluoroborate (ICTB) I have been observed and their mechanisms were proposed and discussed. Intramolecular capture of the early stage cat ionic intermediates by predevised heteroatoms or Friedel-Crafts donors provided two different types of bridged-ring systems.