2-methyl-6-oxo-7-(phenylthio)heptan-3-ol | 173310-51-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-methyl-6-oxo-7-(phenylthio)heptan-3-ol
• CAS: 173310-51-5
• 化学式: C₁₄H₂₀O₂S
• 分子量: 252.378
• InChiKey: GCQDINPPSQIPIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-methyl-6-oxo-7-(phenylthio)heptan-3-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 2-methyl-7-(phenylthio)-3,6-heptandione
  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-异丙基二氢呋喃-2(3H)-酮 、 (phenylthio)methyllithium 以 四氢呋喃 为溶剂， 反应 2.0h， 以54%的产率得到2-methyl-6-oxo-7-(phenylthio)heptan-3-ol
  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.