(S)-6-phenyl-2,3-dihydro-4-oxo-1,4-oxathiine | 253664-43-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧硫杂环己烯
• 英文名称: (S)-6-phenyl-2,3-dihydro-4-oxo-1,4-oxathiine
• 英文别名: (4S)-6-phenyl-2,3-dihydro-1,4-oxathiine 4-oxide
• CAS: 253664-43-6
• 化学式: C₁₀H₁₀O₂S
• 分子量: 194.254
• InChiKey: VCYNTVXNOURBAQ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-6-phenyl-2,3-dihydro-4-oxo-1,4-oxathiine 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到(R)-1-phenyl-2-(vinylsulfinyl)-1-ethanone
  参考文献：
  名称：

  A facile stereospecific synthesis of chiral β-keto sulfoxides

  摘要：

  A synthetic strategy has been devised for the preparation of chiral beta-keto sulfoxides (actually, alpha-vinylsulfinyl ketones) starting from the readily available C-6 substituted 2,3-dihydro-1,4-oxathiines. The procedure, which is characterized by high yields and excellent enantiomeric excesses, represents an improvement in preparation methods for chiral beta-keto sulfoxides. (C) 1999 published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00350-x
• 作为产物：
  描述：

  5,6-dihydro-2-phenyl-1,4-oxathiine 在 titanium(IV) isopropylate 、 D-(-)-酒石酸二乙酯 、 过氧化氢异丙苯 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-6-phenyl-2,3-dihydro-4-oxo-1,4-oxathiine
  参考文献：
  名称：

  A facile stereospecific synthesis of chiral β-keto sulfoxides

  摘要：

  A synthetic strategy has been devised for the preparation of chiral beta-keto sulfoxides (actually, alpha-vinylsulfinyl ketones) starting from the readily available C-6 substituted 2,3-dihydro-1,4-oxathiines. The procedure, which is characterized by high yields and excellent enantiomeric excesses, represents an improvement in preparation methods for chiral beta-keto sulfoxides. (C) 1999 published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00350-x

文献信息

• A facile stereospecific synthesis of chiral β-keto sulfoxides
  作者：Romualdo Caputo、Federico Giordano、Annalisa Guaragna、Giovanni Palumbo、Silvana Pedatella

  DOI：10.1016/s0957-4166(99)00350-x

  日期：1999.9

  A synthetic strategy has been devised for the preparation of chiral beta-keto sulfoxides (actually, alpha-vinylsulfinyl ketones) starting from the readily available C-6 substituted 2,3-dihydro-1,4-oxathiines. The procedure, which is characterized by high yields and excellent enantiomeric excesses, represents an improvement in preparation methods for chiral beta-keto sulfoxides. (C) 1999 published by Elsevier Science Ltd. All rights reserved.