2-<2'-(benzylthio)acetyl>hexahydro-4,4,7-trimethyl-4H-1,3-benzoxathiin | 143429-11-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧硫烷类
• 英文名称: 2-<2'-(benzylthio)acetyl>hexahydro-4,4,7-trimethyl-4H-1,3-benzoxathiin
• 英文别名: 1-[(2R,4aR,7R,8aR)-4,4,7-trimethyl-4a,5,6,7,8,8a-hexahydrobenzo[e][1,3]oxathiin-2-yl]-2-benzylsulfanylethanone
• CAS: 143429-11-2
• 化学式: C₂₀H₂₈O₂S₂
• 分子量: 364.573
• InChiKey: FABCVBAOGWHWNW-YCEFEEMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  溴甲苯 、 alkaline earth salt of/the/ methylsulfuric acid 在 正丁基锂 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 1.17h， 生成 2-<2'-(benzylthio)acetyl>hexahydro-4,4,7-trimethyl-4H-1,3-benzoxathiin
  参考文献：
  名称：

  Convenient synthesis of .alpha.-heterosubstituted acyloxathianes

  摘要：

  In contrast to simple esters, alpha-alkoxy, alpha-alkylthio, and alpha-dimethylamino esters react with lithiooxathiane 1-Li in good yield to give the corresponding alpha-functionalized 2-acetylhexahydro-4,4,7-trimethyl-4H-1,3-benzoxathiin 2. In some cases, mixtures of diastereomers (2, 2') are obtained. The reaction has been extended to alpha-methoxy- and alpha-[(triisopropylsilyl)oxy]propanoyl and alpha-(methylthio)butanoyl homologs which have chiral centers at C(alpha).

  DOI：

  10.1021/jo00045a031

文献信息

• Convenient synthesis of .alpha.-heterosubstituted acyloxathianes
  作者：Xu Bai、Ernest L. Eliel

  DOI：10.1021/jo00045a031

  日期：1992.9

  In contrast to simple esters, alpha-alkoxy, alpha-alkylthio, and alpha-dimethylamino esters react with lithiooxathiane 1-Li in good yield to give the corresponding alpha-functionalized 2-acetylhexahydro-4,4,7-trimethyl-4H-1,3-benzoxathiin 2. In some cases, mixtures of diastereomers (2, 2') are obtained. The reaction has been extended to alpha-methoxy- and alpha-[(triisopropylsilyl)oxy]propanoyl and alpha-(methylthio)butanoyl homologs which have chiral centers at C(alpha).