(E)-8-Benzyloxy-2,2-difluoro-3-hydroxy-oct-6-enoic acid ethyl ester | 145049-22-5

• 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: (E)-8-Benzyloxy-2,2-difluoro-3-hydroxy-oct-6-enoic acid ethyl ester
• CAS: 145049-22-5
• 化学式: C₁₇H₂₂F₂O₄
• 分子量: 328.356
• InChiKey: XIQUIUSRHHNRIH-XBXARRHUSA-N

反应信息

• 作为反应物：
  描述：

  (E)-8-Benzyloxy-2,2-difluoro-3-hydroxy-oct-6-enoic acid ethyl ester 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 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 21.5h， 生成 1,1-difluoro-5-(2-benzyloxy)ethyl-2-(methoxy)methoxycyclohexane
  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：

  二氟溴乙酸乙酯 、 (E)-6-Benzyloxy-hex-4-enal 在 锌 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (E)-8-Benzyloxy-2,2-difluoro-3-hydroxy-oct-6-enoic acid ethyl ester
  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