5-(2-benzyloxyethyl)-3,3-difluoro-2-phenyltetrahydropyran | 145049-79-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(2-benzyloxyethyl)-3,3-difluoro-2-phenyltetrahydropyran
• 英文别名: (2R,5S)-3,3-difluoro-2-phenyl-5-(2-phenylmethoxyethyl)oxane
• CAS: 145049-79-2；145049-80-5
• 化学式: C₂₀H₂₂F₂O₂
• 分子量: 332.39
• InChiKey: PIZBSZXKJKXJFG-PKOBYXMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (Z)-(((4-bromobut-2-en-1-yl)oxy)methyl)benzene 在 偶氮二异丁腈 sodium tetrahydroborate 、 三正丁基氢锡 、 sodium hydride 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 18.5h， 生成 5-(2-benzyloxyethyl)-3,3-difluoro-2-phenyltetrahydropyran
  参考文献：
  名称：

  Cyclization reactions of β,β-difluoroalkyl radicals (-CF2-C·) for synthesizing gem-difluorocyclic compounds

  摘要：

  Cyclization reactions of beta,beta-difluoroalkyl radicals were carried out. 5 or 6-Exo selective radical cyclizations gave gem-difluorocyclopentane or -cyclohexane derivatives in 53 - 96% yields. 2,5-Disubstituted-3,3-difluorotetrahydropyran derivatives were prepared in 36 - 82% yields with moderate trans-selectivity (2.0 : 1-3.1 : 1). 4,5-Disubstituted-3,3-difluorotetrahydopyran derivatives were obtained via radical deoxygenation in 60 - 74% yields. High stereo-selectivity of radical cyclization for the formation of gem-fluorotetrahydropyran rings was achieved by introducing the bulky TBDPS group onto the acceptor double bond.

  DOI：

  10.1016/s0040-4020(01)81990-6

文献信息

• Cyclization reactions of β,β-difluoroalkyl radicals (-CF2-C·) for synthesizing gem-difluorocyclic compounds
  作者：Tsutomu Morikawa、Yoshitoshi Kodama、Jun Uchida、Masami Takano、Yoshiaki Washio、Takeo Taguchi

  DOI：10.1016/s0040-4020(01)81990-6

  日期：1992.1

  Cyclization reactions of beta,beta-difluoroalkyl radicals were carried out. 5 or 6-Exo selective radical cyclizations gave gem-difluorocyclopentane or -cyclohexane derivatives in 53 - 96% yields. 2,5-Disubstituted-3,3-difluorotetrahydropyran derivatives were prepared in 36 - 82% yields with moderate trans-selectivity (2.0 : 1-3.1 : 1). 4,5-Disubstituted-3,3-difluorotetrahydopyran derivatives were obtained via radical deoxygenation in 60 - 74% yields. High stereo-selectivity of radical cyclization for the formation of gem-fluorotetrahydropyran rings was achieved by introducing the bulky TBDPS group onto the acceptor double bond.