2-methyl-7-(phenylthio)-3,6-heptandione | 173310-55-9

• 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-7-(phenylthio)-3,6-heptandione
• 英文别名: 6-Methyl-1-phenylsulfanylheptane-2,5-dione
• CAS: 173310-55-9
• 化学式: C₁₄H₁₈O₂S
• 分子量: 250.362
• InChiKey: TUWWOPMGCSDSSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-7-(phenylthio)-3,6-heptandione 在 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 3-acetoxy-1-isopropyl-4-(methoxycarbonyl)-5-<(phenylthio)methyl>-8-oxabicyclo<3.2.1>oct-3-ene
  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 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 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

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.