dimethyl (4R,5R)-2,2-di(naphthalen-2-yl)-1,3-dioxolane-4,5-dicarboxylate | 1209050-68-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: dimethyl (4R,5R)-2,2-di(naphthalen-2-yl)-1,3-dioxolane-4,5-dicarboxylate
• CAS: 1209050-68-9
• 化学式: C₂₇H₂₂O₆
• 分子量: 442.468
• InChiKey: IVNVYVRKQQQXSR-DNQXCXABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  33.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  dimethyl (4R,5R)-2,2-di(naphthalen-2-yl)-1,3-dioxolane-4,5-dicarboxylate 在 水 、 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 0.17h， 以100%的产率得到(R,R)-2,2-dinaphthalen-2-yl-[1,3]dioxolane-4,5-dicarboxylic acid
  参考文献：
  名称：

  Cyclic Ketals of Tartaric Acid: Simple and Tunable Reagents for the Determination of the Absolute Configuration of Primary Amines

  摘要：

  2,2-Diphenyl-[1,3]dioxolane-4,5-dicarboxylic acid (DPD) and 2,2-dinaphthalen-2-yl-[1,3]dioxolane-4,5-dicarboxylic acid (DND) have been synthesized starting from dimethyl tartrate. DPD and DND amides of alpha-chiral primary amines showed significantly different H-1 chemical shift values depending on the stereochemistry of the derivatizing agent. On the basis of this chemical shift difference, the absolute configuration of amine substrates could be assigned. DND amides showed significantly larger chemical shift differences than the corresponding DPD amides allowing for a more error-free assignment.

  DOI：

  10.1021/ol902942k
• 作为产物：
  描述：

  L-(+)-酒石酸二甲酯 、 2,2'-dinaphthyl ketone dimethylketal 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以81%的产率得到dimethyl (4R,5R)-2,2-di(naphthalen-2-yl)-1,3-dioxolane-4,5-dicarboxylate
  参考文献：
  名称：

  Cyclic Ketals of Tartaric Acid: Simple and Tunable Reagents for the Determination of the Absolute Configuration of Primary Amines

  摘要：

  2,2-Diphenyl-[1,3]dioxolane-4,5-dicarboxylic acid (DPD) and 2,2-dinaphthalen-2-yl-[1,3]dioxolane-4,5-dicarboxylic acid (DND) have been synthesized starting from dimethyl tartrate. DPD and DND amides of alpha-chiral primary amines showed significantly different H-1 chemical shift values depending on the stereochemistry of the derivatizing agent. On the basis of this chemical shift difference, the absolute configuration of amine substrates could be assigned. DND amides showed significantly larger chemical shift differences than the corresponding DPD amides allowing for a more error-free assignment.

  DOI：

  10.1021/ol902942k