phenyl-[(1S,11R,12S)-1-(3,4,5-trimethoxyphenyl)-5,7,19-trioxapentacyclo[10.7.1.02,10.04,8.013,18]icosa-2,4(8),9,13,15,17-hexaen-11-yl]methanone | 1447951-96-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: phenyl-[(1S,11R,12S)-1-(3,4,5-trimethoxyphenyl)-5,7,19-trioxapentacyclo[10.7.1.02,10.04,8.013,18]icosa-2,4(8),9,13,15,17-hexaen-11-yl]methanone
• CAS: 1447951-96-3
• 化学式: C₃₃H₂₈O₇
• 分子量: 536.581
• InChiKey: QELYOUGFIZDBEN-ZYWNIYNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  、 乙酰苯 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， 反应 54.0h， 以77%的产率得到phenyl-[(1S,11R,12S)-1-(3,4,5-trimethoxyphenyl)-5,7,19-trioxapentacyclo[10.7.1.02,10.04,8.013,18]icosa-2,4(8),9,13,15,17-hexaen-11-yl]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