(3aS,8aR)-3-[phenylsulfanyl(trimethylsilyl)methyl]-3,3a,4,5,6,7,8,8a-octahydrocyclohepta[b]furan-2-one | 118522-18-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (3aS,8aR)-3-[phenylsulfanyl(trimethylsilyl)methyl]-3,3a,4,5,6,7,8,8a-octahydrocyclohepta[b]furan-2-one
• CAS: 118522-18-2
• 化学式: C₁₉H₂₈O₂SSi
• 分子量: 348.582
• InChiKey: VJTHCGRJXJXGRQ-HNXFYBAISA-N

物化性质

• 沸点：
  469.3±20.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 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：

  (3aS,8aR)-3-[phenylsulfanyl(trimethylsilyl)methyl]-3,3a,4,5,6,7,8,8a-octahydrocyclohepta[b]furan-2-one 在 四丁基氟化铵 、 丙烯酸甲酯（MA） 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以93%的产率得到trans-10-methylidene-8-oxabicyclo[5.3.0]decan-9-one
  参考文献：
  名称：

  Synthesis of .gamma.- and .delta.-lactones by free-radical annelation of Se-phenyl selenocarbonates

  摘要：

  A general method for the synthesis of gamma- and delta-lactones through the intramolecular addition of alkoxycarbonyl radicals, formed by reaction of Se-phenylselenocarbonates with n-Bu3SnH, onto carbon-carbon multiple bonds is described. This free-radical cyclization is characterized by high regioselectivity favoring exo addition and by a high ratio of cyclization to reduction. Monocyclic, fused bicyclic, and spirocyclic lactones are formed in good to excellent yield. Use of allyltri-n-butyltin as a chain-transfer agent in the place of n-Bu3SnH affords the corresponding 3-butenyl lactones.

  DOI：

  10.1021/jo00043a030
• 作为产物：
  描述：

  (1R,2S)-2-(2-trimethylsilylethynyl)cycloheptan-1-ol 在 吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 3.5h， 生成 (3aS,8aR)-3-[phenylsulfanyl(trimethylsilyl)methyl]-3,3a,4,5,6,7,8,8a-octahydrocyclohepta[b]furan-2-one
  参考文献：
  名称：

  Synthesis of .gamma.- and .delta.-lactones by free-radical annelation of Se-phenyl selenocarbonates

  摘要：

  A general method for the synthesis of gamma- and delta-lactones through the intramolecular addition of alkoxycarbonyl radicals, formed by reaction of Se-phenylselenocarbonates with n-Bu3SnH, onto carbon-carbon multiple bonds is described. This free-radical cyclization is characterized by high regioselectivity favoring exo addition and by a high ratio of cyclization to reduction. Monocyclic, fused bicyclic, and spirocyclic lactones are formed in good to excellent yield. Use of allyltri-n-butyltin as a chain-transfer agent in the place of n-Bu3SnH affords the corresponding 3-butenyl lactones.

  DOI：

  10.1021/jo00043a030

文献信息

• Synthesis of .gamma.- and .delta.-lactones by free-radical annelation of Se-phenyl selenocarbonates
  作者：Mario D. Bachi、Eric Bosch

  DOI：10.1021/jo00043a030

  日期：1992.8

  A general method for the synthesis of gamma- and delta-lactones through the intramolecular addition of alkoxycarbonyl radicals, formed by reaction of Se-phenylselenocarbonates with n-Bu3SnH, onto carbon-carbon multiple bonds is described. This free-radical cyclization is characterized by high regioselectivity favoring exo addition and by a high ratio of cyclization to reduction. Monocyclic, fused bicyclic, and spirocyclic lactones are formed in good to excellent yield. Use of allyltri-n-butyltin as a chain-transfer agent in the place of n-Bu3SnH affords the corresponding 3-butenyl lactones.