(R,R)-(+)-2,2'-Dimethyl-4-(1-naphthyl)-5-(2-naphthyl)-1,3-dioxolane

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (R,R)-(+)-2,2'-Dimethyl-4-(1-naphthyl)-5-(2-naphthyl)-1,3-dioxolane
• 英文别名: (4R,5R)-2,2-dimethyl-4-naphthalen-1-yl-5-naphthalen-2-yl-1,3-dioxolane
• 化学式: C₂₅H₂₂O₂
• 分子量: 354.448
• InChiKey: HZZFNXYKOKFIRJ-DNQXCXABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,2-二甲氧基丙烷 、 1-(1-Naphthyl)-2-(2-naphthyl)ethane-1,2-diol 在 4 A molecular sieve 、 对甲苯磺酸 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以92%的产率得到(R,R)-(+)-2,2'-Dimethyl-4-(1-naphthyl)-5-(2-naphthyl)-1,3-dioxolane
  参考文献：
  名称：

  Synthesis and Stereochemical Characterization of Some Optically Active 1,2-Dinaphthylethane-1,2-Diols

  摘要：

  Three new diols, 1,2-di(2-naphthyl)ethane-1,2-diol, 1-(1-naphthyl)-2-(2-naphthyl)ethane-1,2-diol, and 1,2-di(1-naphthyl)ethane-1,2-diol, have been prepared in optically active form by catalytic asymmetric syn-dihydroxylation of the corresponding (E)-olefins. The complete stereochemical characterization was easily accomplished by transforming them into the corresponding isopropylidene ketals. These derivatives can be separated by HPLC on a Chiralcel OD column allowing the determination of the ee, and at same time, their CD spectra have been analyzed, allowing a safe assignment of absolute configuration in conjunction with molecular mechanics calculations and an exciton-coupling treatment.

  DOI：

  10.1021/jo00103a035

文献信息

• Synthesis and Stereochemical Characterization of Some Optically Active 1,2-Dinaphthylethane-1,2-Diols
  作者：Carlo Rosini、Simone Scamuzzi、Gloria Uccello-Barretta、Piero Salvadori

  DOI：10.1021/jo00103a035

  日期：1994.12

  Three new diols, 1,2-di(2-naphthyl)ethane-1,2-diol, 1-(1-naphthyl)-2-(2-naphthyl)ethane-1,2-diol, and 1,2-di(1-naphthyl)ethane-1,2-diol, have been prepared in optically active form by catalytic asymmetric syn-dihydroxylation of the corresponding (E)-olefins. The complete stereochemical characterization was easily accomplished by transforming them into the corresponding isopropylidene ketals. These derivatives can be separated by HPLC on a Chiralcel OD column allowing the determination of the ee, and at same time, their CD spectra have been analyzed, allowing a safe assignment of absolute configuration in conjunction with molecular mechanics calculations and an exciton-coupling treatment.