2,2-dimethyl-5-fluoro-5-hydroxymethyl-1,3-dioxane | 133384-80-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dimethyl-5-fluoro-5-hydroxymethyl-1,3-dioxane
• 英文别名: (5-Fluoro-2,2-dimethyl-1,3-dioxan-5-yl)methanol
• CAS: 133384-80-2
• 化学式: C₇H₁₃FO₃
• 分子量: 164.177
• InChiKey: CFKRJTKMGKMTTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸酐 、 2,2-dimethyl-5-fluoro-5-hydroxymethyl-1,3-dioxane 在 lutidine 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以79%的产率得到2,2-dimethyl-5-fluoro-5-trifluoromethanesulfonyloxymethyl-1,3-dioxane
  参考文献：
  名称：

  Synthesis of 5,5′-dihydroxyleucine and 4-fluoro 5,5′-dihydroxyleucine, the reduction products of 4-carboxyglutamic and 4-carboxy-4-fluoroglutamic acids

  摘要：

  Schemes for the synthesis of 5-5'-dihydroxyleucine 3 and its 4-fluoro analog 7 involving the condensation of a suitable ''aminoacid moiety'' with 2,2-dimethyl-5-iodomethyl-1,3-dioxane 15D or its fluoro analog 27A were tested. The anion of the ethyl N-diphenylmethylene-glycinate 25 gave better yields of 3 than the classical anion of diethyl acetamidomalonate. This strategy could not be successfully applied to the synthesis of 7, which could be prepared by reduction of a suitably protected 4-fluoro-4-carboxyglutamate with BMS.

  DOI：

  10.1016/s0040-4020(01)80939-x
• 作为产物：
  描述：

  2,2-dimethyl-5-benzyloxymethyl-5-fluoro-1,3-dioxane 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.5h， 以97%的产率得到2,2-dimethyl-5-fluoro-5-hydroxymethyl-1,3-dioxane
  参考文献：
  名称：

  Synthesis of 5,5′-dihydroxyleucine and 4-fluoro 5,5′-dihydroxyleucine, the reduction products of 4-carboxyglutamic and 4-carboxy-4-fluoroglutamic acids

  摘要：

  Schemes for the synthesis of 5-5'-dihydroxyleucine 3 and its 4-fluoro analog 7 involving the condensation of a suitable ''aminoacid moiety'' with 2,2-dimethyl-5-iodomethyl-1,3-dioxane 15D or its fluoro analog 27A were tested. The anion of the ethyl N-diphenylmethylene-glycinate 25 gave better yields of 3 than the classical anion of diethyl acetamidomalonate. This strategy could not be successfully applied to the synthesis of 7, which could be prepared by reduction of a suitably protected 4-fluoro-4-carboxyglutamate with BMS.

  DOI：

  10.1016/s0040-4020(01)80939-x

文献信息

• Synthesis of 5,5′-dihydroxyleucine and 4-fluoro 5,5′-dihydroxyleucine, the reduction products of 4-carboxyglutamic and 4-carboxy-4-fluoroglutamic acids
  作者：Joëlle Dubois、Christine Fourès、Sonia Bory、Serge Falcou、Michel Gaudry、Andrée Marquet

  DOI：10.1016/s0040-4020(01)80939-x

  日期：1991.1

  Schemes for the synthesis of 5-5'-dihydroxyleucine 3 and its 4-fluoro analog 7 involving the condensation of a suitable ''aminoacid moiety'' with 2,2-dimethyl-5-iodomethyl-1,3-dioxane 15D or its fluoro analog 27A were tested. The anion of the ethyl N-diphenylmethylene-glycinate 25 gave better yields of 3 than the classical anion of diethyl acetamidomalonate. This strategy could not be successfully applied to the synthesis of 7, which could be prepared by reduction of a suitably protected 4-fluoro-4-carboxyglutamate with BMS.