4-oxo-2-(phenylthio)pentanal | 173310-64-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-oxo-2-(phenylthio)pentanal
• 英文别名: 4-Oxo-2-phenylsulfanylpentanal
• CAS: 173310-64-0
• 化学式: C₁₁H₁₂O₂S
• 分子量: 208.281
• InChiKey: UACFVSRYIIAXKH-UHFFFAOYSA-N

物化性质

• 沸点：
  319.7±37.0 °C(predicted)
• 密度：
  1.14±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  4-oxo-2-(phenylthio)pentanal 在 三氟甲磺酸三甲基硅酯 、 对甲苯磺酸 、 sodium chloride 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 、 苯 为溶剂， 反应 30.5h， 生成 (1R*,5S*,6R*)-1-methyl-6-(phenylthio)-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：

  methyl 2-chloro-2-(phenylsulfanyl)acetate 在 盐酸 、 lithium aluminium tetrahydride 、 草酰氯 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 、 zinc dibromide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 54.25h， 生成 4-oxo-2-(phenylthio)pentanal
  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

• Synthesis of Cyclic Bis(trimethysilyl) Enol Ethers and Their [3 + 4] and [3 + 5] Annulation Reactions with Dicarbonyl Electrophiles. Access to Highly Functionalized Tricyclic Ethers Possessing Trans Intrabridgehead Stereochemistry
  作者：Gary A. Molander、Bernard Bessières、Paul R. Eastwood、Bruce C. Noll

  DOI：10.1021/jo9902547

  日期：1999.5.1

  The synthesis of cyclic bis(trimethylsilyl) enol ethers from cycloalkanone carboxylates is described. The [3 + 4] and [3 + 5] annulation reactions of these bis(dinucleophilic), synthons with various 1,4- and 1,5-dicarbonyl electrophiles leads to the formation of tricyclic keto ethers with good regio- and stereochemical control. An interesting trans intrabridgehead stereochemistry is observed when using bis(trimethylsilyl) enol ethers derived from nine- to 12-membered ring beta-keto esters.
• [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.