1-benzyl-5-(difluoro(phenylsulfanyl)methyl)-5-hydroxy-pyrrolidin-2-one | 1152032-86-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-benzyl-5-(difluoro(phenylsulfanyl)methyl)-5-hydroxy-pyrrolidin-2-one
• 英文别名: 1-benzyl-5-(difluoro(phenylsulfanyl)methyl)-5-hydroxypyrrolidin-2-one；1-Benzyl-5-[difluoro(phenylsulfanyl)methyl]-5-hydroxypyrrolidin-2-one
• CAS: 1152032-86-4
• 化学式: C₁₈H₁₇F₂NO₂S
• 分子量: 349.401
• InChiKey: ROZNSXMMSDWZLM-UHFFFAOYSA-N

物化性质

• 熔点：
  125-126 °C
• 沸点：
  503.5±50.0 °C(predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-benzyl-5-(difluoro(phenylsulfanyl)methyl)-5-hydroxy-pyrrolidin-2-one 在 三乙基硅烷 、 偶氮二异丁腈 、 三氟化硼乙醚 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 1-benzyl-5-(difluoromethyl)pyrrolidin-2-one
  参考文献：
  名称：

  Fluoride-catalyzed nucleophilic addition of PhSCF2SiMe3 to anhydrides: synthesis of γ-difluoromethylated γ-lactams

  摘要：

  PhSCF2SiMe3 (1) 在氟化物催化下与酸酐的羰基发生亲核加成反应，生成相应的 δ³-difluoro(phensulfanyl)methyl δ³-lactols ，并用于合成 δ³-difluoromethylated δ³-lactams 。

  DOI：

  10.1039/c3ob27193e
• 作为产物：
  描述：

  [二氟(苯硫基)甲基]三甲基硅烷 在 对甲苯磺酸 、 四丁基二氟三苯硅酸铵 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.0h， 生成 1-benzyl-5-(difluoro(phenylsulfanyl)methyl)-5-hydroxy-pyrrolidin-2-one
  参考文献：
  名称：

  Fluoride-catalyzed nucleophilic addition of PhSCF2SiMe3 to anhydrides: synthesis of γ-difluoromethylated γ-lactams

  摘要：

  PhSCF2SiMe3 (1) 在氟化物催化下与酸酐的羰基发生亲核加成反应，生成相应的 δ³-difluoro(phensulfanyl)methyl δ³-lactols ，并用于合成 δ³-difluoromethylated δ³-lactams 。

  DOI：

  10.1039/c3ob27193e

文献信息

• Fluoride-Catalyzed Addition of PhSCF₂SiMe₃ to <i>N</i>-Substituted Cyclic Imides Followed by Radical Cyclization: General Synthetic Strategy of <i>gem</i>-Difluoromethylenated 1-Azabicyclic Compounds
  作者：Teerawut Bootwicha、Duanghathai Panichakul、Chutima Kuhakarn、Samran Prabpai、Palangpon Kongsaeree、Patoomratana Tuchinda、Vichai Reutrakul、Manat Pohmakotr

  DOI：10.1021/jo802794u

  日期：2009.5.15

  PhSCF2SiMe3 (1) was found, for the first time, to undergo fluoride-catalyzed nucleophilic difluoro-(phenylsulfanyl)methylation reaction to cyclic imides 2, affording the corresponding adducts 3 in moderate to good yields. Reductive cleavage of the phenylsulfanyl group of N-alkylated adducts 3 with Bu3SnH/AIBN yielded gem-difluoromethylated products 4. Under the same reduction conditions, N-alkenylated and N-alkynylated adducts 3 afforded the corresponding gem-difluoromethylenated 1-azabicyclic compounds 5 and 6 with trans stereoselectivity. These compounds were employed as precursors for preparing substituted gem-difluoromethylenated pyrrolizidinones and indolizidinones 7 and 8 by treatment with Et3SiH/BF3 center dot OEt2, and compounds 9 and 10 by nucleophilic displacement of the hydroxyl group, using organosilanes in the presence of BF3 center dot OEt2. The synthesis of highly substituted gem-difluoromethylenated pyrrolizidines 13 and 14 was also demonstrated.
• Fluoride-catalyzed nucleophilic addition of PhSCF2SiMe3 to anhydrides: synthesis of γ-difluoromethylated γ-lactams
  作者：Vannapha Pharikronburee、Teerachai Punirun、Darunee Soorukram、Chutima Kuhakarn、Patoomratana Tuchinda、Vichai Reutrakul、Manat Pohmakotr

  DOI：10.1039/c3ob27193e

  日期：——

  PhSCF2SiMe3 (1) underwent fluoride-catalyzed nucleophilic addition to the carbonyl group of anhydrides to provide the corresponding γ-difluoro(phenylsulfanyl)methyl γ-lactols, which were employed for the synthesis of γ-difluoromethylated γ-lactams.

  PhSCF2SiMe3 (1) 在氟化物催化下与酸酐的羰基发生亲核加成反应，生成相应的 δ³-difluoro(phensulfanyl)methyl δ³-lactols ，并用于合成 δ³-difluoromethylated δ³-lactams 。