1,1-difluoro-5-(carbethoxy)methyl-2-(methoxy)methoxycyclohexane | 145049-69-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: 1,1-difluoro-5-(carbethoxy)methyl-2-(methoxy)methoxycyclohexane
• 英文别名: Ethyl 2-[3,3-difluoro-4-(methoxymethoxy)cyclohexyl]acetate
• CAS: 145049-69-0；145049-70-3
• 化学式: C₁₂H₂₀F₂O₄
• 分子量: 266.285
• InChiKey: MJYUMHUPIPROLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl (2E)-6-oxohex-2-enoate 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 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 23.5h， 生成 1,1-difluoro-5-(carbethoxy)methyl-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

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.