(R)-3-[(5-(dimethylamino)naphthalene-1-sulfonyl)oxy]tetrahydrothiophene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-3-[(5-(dimethylamino)naphthalene-1-sulfonyl)oxy]tetrahydrothiophene
• 英文别名: [(3R)-thiolan-3-yl] 5-(dimethylamino)naphthalene-1-sulfonate
• 化学式: C₁₆H₁₉NO₃S₂
• 分子量: 337.464
• InChiKey: QDWGKOOORSHYOK-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  四氢-噻吩-3-醇 、 丹酰氯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-3-[(5-(dimethylamino)naphthalene-1-sulfonyl)oxy]tetrahydrothiophene 、 (S)-3-[(5-(dimethylamino)naphthalene-1-sulfonyl)oxy]tetrahydrothiophene
  参考文献：
  名称：

  Enantiomeric purity enrichment of (R)-tetrahydrothiophene-3-ol sulfonyl derivatives by crystallization

  摘要：

  (R)-Tetrahydrothiophene-3-ol sulfonyl derivatives 3-19 were prepared by introduction of various sulfonyl groups at the hydroxyl group of (R)-tetrahydrothiophene-3-ol 1 with low enantiomeric purity (68-74% ee). Crystallization was applied to improve their enantiomeric purity. Improvement in enantiomeric purity depended on the introduced sulfonyl group. The enantiomeric purity of enantiomeric sulfonyl derivatives was improved to more than 90% ee by simple crystallization without using seed crystals. These products from crystallization provided not only higher %ee crystals but also a higher %ee mother liquor. The enantiomeric purity of diastereomeric sulfonyl derivatives was improved remarkably, and the product of the derivative 18 provided the mother liquor with 100% de. Crystallization of these sulfonyl derivatives showed a novel and interesting feature that mother liquors with high enantiomeric purity were obtained in many cases. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.10.020

文献信息

• Enantiomeric purity enrichment of (R)-tetrahydrothiophene-3-ol sulfonyl derivatives by crystallization
  作者：Kaname Konuki、Hazuki Nagai

  DOI：10.1016/j.tetasy.2014.10.020

  日期：2014.12

  (R)-Tetrahydrothiophene-3-ol sulfonyl derivatives 3-19 were prepared by introduction of various sulfonyl groups at the hydroxyl group of (R)-tetrahydrothiophene-3-ol 1 with low enantiomeric purity (68-74% ee). Crystallization was applied to improve their enantiomeric purity. Improvement in enantiomeric purity depended on the introduced sulfonyl group. The enantiomeric purity of enantiomeric sulfonyl derivatives was improved to more than 90% ee by simple crystallization without using seed crystals. These products from crystallization provided not only higher %ee crystals but also a higher %ee mother liquor. The enantiomeric purity of diastereomeric sulfonyl derivatives was improved remarkably, and the product of the derivative 18 provided the mother liquor with 100% de. Crystallization of these sulfonyl derivatives showed a novel and interesting feature that mother liquors with high enantiomeric purity were obtained in many cases. (C) 2014 Elsevier Ltd. All rights reserved.