(Z)-(1-((4-(benzyloxy)but-2-en-1-yl)oxy)-2,2-difluoro-3-iodopropyl)benzene | 145049-51-0

• 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: (Z)-(1-((4-(benzyloxy)but-2-en-1-yl)oxy)-2,2-difluoro-3-iodopropyl)benzene
• CAS: 145049-51-0
• 化学式: C₂₀H₂₁F₂IO₂
• 分子量: 458.287
• InChiKey: FWFXBNGFJJAOHY-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.59
• 重原子数：
  25.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (Z)-(1-((4-(benzyloxy)but-2-en-1-yl)oxy)-2,2-difluoro-3-iodopropyl)benzene 在 偶氮二异丁腈 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 2.0h， 以45%的产率得到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
• 作为产物：
  描述：

  3-((Z)-4-Benzyloxy-but-2-enyloxy)-2,2-difluoro-3-phenyl-propionic acid ethyl ester 在 sodium tetrahydroborate 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 16.5h， 生成 (Z)-(1-((4-(benzyloxy)but-2-en-1-yl)oxy)-2,2-difluoro-3-iodopropyl)benzene
  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