5-methyl-1-<(phenylthio)methyl>-8-oxabicyclo<3.2.1>octan-3-one

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-methyl-1-<(phenylthio)methyl>-8-oxabicyclo<3.2.1>octan-3-one
• 英文别名: (1R,5S)-1-methyl-5-(phenylsulfanylmethyl)-8-oxabicyclo[3.2.1]octan-3-one
• 化学式: C₁₅H₁₈O₂S
• 分子量: 262.373
• InChiKey: SCXKIOAITUCDSM-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methyl-1-<(phenylthio)methyl>-8-oxabicyclo<3.2.1>octan-3-one 在 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 25.0h， 生成 5-methyl-1-<(phenylsulfonyl)methyl>-8-oxabicyclo<3.2.1>octan-3-one, ethylene acetal
  参考文献：
  名称：

  [3 + 4] and [3 + 5] Annulation Reactions of .alpha.-(Phenylthio)Dicarbonyl Electrophiles with Bis(trimethylsilyl) Enol Ethers: Synthesis of Highly Functionalized Medium Ring Carbocycles

  摘要：

  The [3 + 4] and [3 + 5] annulations of bis(trimethylsilyl) enol ethers with 1,4- and 1,5-dicarbonyl electrophiles bearing alpha-phenylthio substituents leads to the formation of bicyclic [3.2.1] and [3.3.1] ethers with good regiochemical and stereochemical control, Subsequent oxidation of the phenylthio moiety followed by reduction with SmI2 constitutes a high-yielding and regioselective process for cleavage of the bridging ether linkage. The overall strategy provides a synthetic pathway for the synthesis of highly functionalized medium ring carbocycles.

  DOI：

  10.1021/jo00131a013
• 作为产物：
  描述：

  5-oxo-6-(phenylthio)hexan-2-ol 在 草酰氯 、 三氟甲磺酸三甲基硅酯 、 二甲基亚砜 、 三乙胺 、 sodium chloride 作用下， 以 二氯甲烷 为溶剂， 反应 13.75h， 生成 5-methyl-1-<(phenylthio)methyl>-8-oxabicyclo<3.2.1>octan-3-one
  参考文献：
  名称：

  [3 + 4] and [3 + 5] Annulation Reactions of .alpha.-(Phenylthio)Dicarbonyl Electrophiles with Bis(trimethylsilyl) Enol Ethers: Synthesis of Highly Functionalized Medium Ring Carbocycles

  摘要：

  The [3 + 4] and [3 + 5] annulations of bis(trimethylsilyl) enol ethers with 1,4- and 1,5-dicarbonyl electrophiles bearing alpha-phenylthio substituents leads to the formation of bicyclic [3.2.1] and [3.3.1] ethers with good regiochemical and stereochemical control, Subsequent oxidation of the phenylthio moiety followed by reduction with SmI2 constitutes a high-yielding and regioselective process for cleavage of the bridging ether linkage. The overall strategy provides a synthetic pathway for the synthesis of highly functionalized medium ring carbocycles.

  DOI：

  10.1021/jo00131a013

文献信息

• [3 + 4] and [3 + 5] Annulation Reactions of .alpha.-(Phenylthio)Dicarbonyl Electrophiles with Bis(trimethylsilyl) Enol Ethers: Synthesis of Highly Functionalized Medium Ring Carbocycles
  作者：Gary A. Molander、Paul R. Eastwood

  DOI：10.1021/jo00131a013

  日期：1995.12

  The [3 + 4] and [3 + 5] annulations of bis(trimethylsilyl) enol ethers with 1,4- and 1,5-dicarbonyl electrophiles bearing alpha-phenylthio substituents leads to the formation of bicyclic [3.2.1] and [3.3.1] ethers with good regiochemical and stereochemical control, Subsequent oxidation of the phenylthio moiety followed by reduction with SmI2 constitutes a high-yielding and regioselective process for cleavage of the bridging ether linkage. The overall strategy provides a synthetic pathway for the synthesis of highly functionalized medium ring carbocycles.