methyl 4-((2-formyl-4,5-dimethoxyphenyl)ethynyl)benzoate | 1447951-01-0

• 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: methyl 4-((2-formyl-4,5-dimethoxyphenyl)ethynyl)benzoate
• CAS: 1447951-01-0
• 化学式: C₁₉H₁₆O₅
• 分子量: 324.333
• InChiKey: VMOWAYSKOXIIMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 4-((2-formyl-4,5-dimethoxyphenyl)ethynyl)benzoate 、 乙酰苯 在 (S)-3,3'-bis(2,4,6-tri-iso-propylphenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate 、 palladium diacetate 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 以78%的产率得到methyl 4-((6S,11S,12R)-8,9-dimethoxy-11,12-dihydro-6H-6,12-methanodibenzo[b,f]oxocine-11-carbonyl)benzoate
  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