(E)-7,7-Difluoro-6-methoxymethoxy-oct-2-enedioic acid diethyl ester | 145049-24-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-7,7-Difluoro-6-methoxymethoxy-oct-2-enedioic acid diethyl ester
• CAS: 145049-24-7
• 化学式: C₁₄H₂₂F₂O₆
• 分子量: 324.322
• InChiKey: JZYTZUFTQAUBPF-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  22.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (E)-7,7-Difluoro-6-methoxymethoxy-oct-2-enedioic acid diethyl 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 (E)-7,7-Difluoro-8-iodo-6-methoxymethoxy-oct-2-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
• 作为产物：
  描述：

  ethyl (2E)-6-oxohex-2-enoate 在 sodium hydride 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (E)-7,7-Difluoro-6-methoxymethoxy-oct-2-enedioic acid diethyl 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