rac-4-(1-naphthyloxymethyl)-2,2-dioxo-1,3,2-dioxathiolane | 1262044-32-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: rac-4-(1-naphthyloxymethyl)-2,2-dioxo-1,3,2-dioxathiolane
• 英文别名: 4-(naphthalen-1-yloxymethyl)-1,3,2-dioxathiolane 2,2-dioxide
• CAS: 1262044-32-5
• 化学式: C₁₃H₁₂O₅S
• 分子量: 280.301
• InChiKey: QSIJZSXNOQOXBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  3-(1-萘基氧基)-1,2-丙二醇 在 磺酰氯 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 3.5h， 生成 rac-4-(1-naphthyloxymethyl)-2,2-dioxo-1,3,2-dioxathiolane
  参考文献：
  名称：

  Synthesis and solid state properties of the 4-naphthyloxymethyl-2,2-dioxo-1,3,2-dioxathiolane, cyclic sulfate not available through sulfite oxidation procedure

  摘要：

  The chiral adrenoblocker propranolol precursor 4-naphthyloxymethyl-2,2-diozo-1,3,2-dioxathiolane, 2, was obtained in racemic and scalemic form. It was found that sulfates 2 are practically unavailable through the standard Ru-catalyzed sulfite oxidation procedure, but could be obtained by the direct action of SO2Cl2 on the corresponding vicinal diols 3. The published properties of the sulfate were corrected. Thermodynamic characteristics and binary melting phase diagram were evaluated for compound 2 by DSC. The crystal structure of rac- and scal-2 was established by single crystal X-ray analysis and the absolute configuration of scal-2 was established by the Flack method. The flexible nature of the sulfur-containing cycle, and the sensitivity of the compound conformation to homo- and heterochiral crystal environment was demonstrated. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2010.09.053