| 1208234-94-9

• 分子结构分类: 有机化合物 - 有机硫化合物
• CAS: 1208234-94-9
• 化学式: C₁₄H₁₈O₃S
• 分子量: 266.361
• InChiKey: WGASTIVHPPCKHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  在 nickel(II) perchlorate hexahydrate 、 N-氟代双苯磺酰胺 、 (4R,4'R)-2,2'-(4,6-二苯并呋喃二基)双[4,5-二氢-4-苯基恶唑] 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 tert-butyl 2-fluoro-3-oxo-2-(phenylsulfanyl)butanoate 、 tert-butyl 2-fluoro-3-oxo-2-(phenylsulfanyl)butanoate
  参考文献：
  名称：

  Asymmetric synthesis of α-fluoro-α-sulfenyl-β-ketoesters using DBFOX–Ph/Ni(II) complex

  摘要：

  Enantioselective alpha-sulfenylation of alpha-fluoro-beta-ketoesters 4 with phenylsulfenyl chloride catalyzed by DBFOX-Ph/Ni(II) complex afforded the corresponding alpha-fluoro-alpha-sulfenyl-beta-ketoesters 2 in moderate to good yields with excellent enantiomeric excesses up to 93% ee. alpha-Fluoro-alpha-sulfenyl-beta-ketoesters can be effectively converted to tri-fluorinated alpha-sulfenylcarboxylates by the use of DAST, which should be useful intermediates for the synthesis of non-racemized fluorinated isosteres of pharmaceutically attractive SM32. The enantioselective alpha-phenylsulfenylation as well as alpha-pentafluoro-phenylsulfenylation of non-fluorinated beta-ketoesters 5 were also carried out under the same catalyst conditions affording up to 95% ee of the products 6-8. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2009.08.004