(R,R)-2,2-dinaphthalen-2-yl-[1,3]dioxolane-4,5-dicarboxylic acid | 1209050-66-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R,R)-2,2-dinaphthalen-2-yl-[1,3]dioxolane-4,5-dicarboxylic acid
• 英文别名: (4R,5R)-2,2-dinaphthalen-2-yl-1,3-dioxolane-4,5-dicarboxylic acid
• CAS: 1209050-66-7
• 化学式: C₂₅H₁₈O₆
• 分子量: 414.414
• InChiKey: WCVFPRAEKPHGRL-FGZHOGPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  L-亮氨醇 、 (R,R)-2,2-dinaphthalen-2-yl-[1,3]dioxolane-4,5-dicarboxylic acid 在 双(2-氧代-3-恶唑烷基)次磷酰氯 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (4R,5R)-N4,N5-bis((S)-1-hydroxy-4-methylpentan-2-yl)-2,2-di(naphthalen-2-yl)-1,3-dioxolane-4,5-dicarboxamide
  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：

  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

文献信息

• Cyclic Ketals of Tartaric Acid: Simple and Tunable Reagents for the Determination of the Absolute Configuration of Primary Amines
  作者：You-Jin Shim、Kihang Choi

  DOI：10.1021/ol902942k

  日期：2010.2.19

  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.