rac-5-(1-naphthyl)-5-trifluoromethyl-[1,3]-dioxolane-2,4-dione | 1058658-47-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: rac-5-(1-naphthyl)-5-trifluoromethyl-[1,3]-dioxolane-2,4-dione
• 英文别名: 5-(Trifluoromethyl)-5-(1-naphthyl)-1,3-dioxolane-2,4-dione；5-naphthalen-1-yl-5-(trifluoromethyl)-1,3-dioxolane-2,4-dione
• CAS: 1058658-47-1
• 化学式: C₁₄H₇F₃O₄
• 分子量: 296.202
• InChiKey: UAQVKCQNTQXXGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  rac-5-(1-naphthyl)-5-trifluoromethyl-[1,3]-dioxolane-2,4-dione 、 R(+)-alpha-甲基苄胺 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (S)-3,3,3-trifluoro-2-hydroxy-2-(1-naphthyl)-N-((R)-1-phenylethyl)propionamide 、 (R)-3,3,3-trifluoro-2-hydroxy-2-(1-naphthyl)-N-((R)-1-phenylethyl)propionamide
  参考文献：
  名称：

  (1-Naphthyl)(trifluoromethyl) O-Carboxy Anhydride as a Chiral Derivatizing Agent: Eclipsed Conformation Enforced by Hydrogen Bonding

  摘要：

  The preparation of the (1-naphthyl)(trifluoromethyl) O-carboxy-anhydride 1 and its use as a chiral derivatizing agent with several a-chiral primary amines are reported. The very large Delta delta(RS) values observed in H-1 NMR have been correlated with a marked preference of the corresponding alpha-hydroxy-am ides for the eclipsed conformation. In comparison, the related O-methylated amides are shown to adopt staggered conformations, which substantiates the critical role of intramolecular hydrogen bonding in maximizing the anisotropic effect.

  DOI：

  10.1021/ol801930m
• 作为产物：
  描述：

  三氯乙酰氯 、 3,3,3-trifluoro-2-hydroxy-2-(1-naphthyl)propanoic acid 在 polystyrene supported diisopropylethylamine 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以68%的产率得到rac-5-(1-naphthyl)-5-trifluoromethyl-[1,3]-dioxolane-2,4-dione
  参考文献：
  名称：

  (1-Naphthyl)(trifluoromethyl) O-Carboxy Anhydride as a Chiral Derivatizing Agent: Eclipsed Conformation Enforced by Hydrogen Bonding

  摘要：

  The preparation of the (1-naphthyl)(trifluoromethyl) O-carboxy-anhydride 1 and its use as a chiral derivatizing agent with several a-chiral primary amines are reported. The very large Delta delta(RS) values observed in H-1 NMR have been correlated with a marked preference of the corresponding alpha-hydroxy-am ides for the eclipsed conformation. In comparison, the related O-methylated amides are shown to adopt staggered conformations, which substantiates the critical role of intramolecular hydrogen bonding in maximizing the anisotropic effect.

  DOI：

  10.1021/ol801930m