2-(4-fluoro-1,8,8-trimethyl-2-oxa-bicyclo[3.2.1]oct-3-yloxy)-propionic acid | 634152-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环丁烷
• 英文名称: 2-(4-fluoro-1,8,8-trimethyl-2-oxa-bicyclo[3.2.1]oct-3-yloxy)-propionic acid
• CAS: 634152-51-5
• 化学式: C₁₃H₂₁FO₄
• 分子量: 260.306
• InChiKey: RVSGJIWXLPLQMP-FTJJUOQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(4-fluoro-1,8,8-trimethyl-2-oxa-bicyclo[3.2.1]oct-3-yloxy)-propionic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-(4-fluoro-1,8,8-trimethyl-2-oxa-bicyclo[3.2.1]oct-3-yloxy)-2-oxopentanoic acid methyl ester
  参考文献：
  名称：

  A camphor-derived chiral auxiliary for hydroxyalkyl radicals

  摘要：

  A new camphor-derived chiral auxiliary for hydroxyalkyl radicals is described. The auxiliary is prepared by the Baeyer-Villiger oxidation of 3-fluorocamphor 12 to give lactone 14, followed by its reduction to the lactol 16. Compound 16 is converted to the acetal-ester 17 and then on to radical precursor 18. A key feature of this auxiliary is the incorporation of a fluorine atom at C-3 (pyranoside numbering), which accelerates the Baeyer-Villiger reaction, results in complete anomeric control during auxiliary attachment. and stabilizes the resulting acetal center. The chiral radical derived from carboxylic acid 18 adds to methyl 2-trifluoroacetoxyacrylate to give adducts 22 and 23 with good diastereocontrol (ds from 3:1 at 0 degreesC up to 4.5:1 at -78 degreesC). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.07.014
• 作为产物：
  描述：

  4-fluoro-1,8,8-trimethyl-2-oxa-bicyclo[3.2.1]octan-3-one 在 sodium hydroxide 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.5h， 生成 2-(4-fluoro-1,8,8-trimethyl-2-oxa-bicyclo[3.2.1]oct-3-yloxy)-propionic acid
  参考文献：
  名称：

  A camphor-derived chiral auxiliary for hydroxyalkyl radicals

  摘要：

  A new camphor-derived chiral auxiliary for hydroxyalkyl radicals is described. The auxiliary is prepared by the Baeyer-Villiger oxidation of 3-fluorocamphor 12 to give lactone 14, followed by its reduction to the lactol 16. Compound 16 is converted to the acetal-ester 17 and then on to radical precursor 18. A key feature of this auxiliary is the incorporation of a fluorine atom at C-3 (pyranoside numbering), which accelerates the Baeyer-Villiger reaction, results in complete anomeric control during auxiliary attachment. and stabilizes the resulting acetal center. The chiral radical derived from carboxylic acid 18 adds to methyl 2-trifluoroacetoxyacrylate to give adducts 22 and 23 with good diastereocontrol (ds from 3:1 at 0 degreesC up to 4.5:1 at -78 degreesC). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.07.014