(1R,4R,5S)-4-Fluoro-1,8,8-trimethyl-3-oxa-bicyclo[3.2.1]octan-2-one | 634152-48-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1R,4R,5S)-4-Fluoro-1,8,8-trimethyl-3-oxa-bicyclo[3.2.1]octan-2-one
• 英文别名: (1R,4R,5S)-4-Fluoro-1,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-one；(1R,4R,5S)-4-fluoro-1,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-one
• CAS: 634152-48-0
• 化学式: C₁₀H₁₅FO₂
• 分子量: 186.226
• InChiKey: RKXLLZZBIORHII-FWWHASMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-fluoro-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以36%的产率得到4-fluoro-1,8,8-trimethyl-2-oxa-bicyclo[3.2.1]octan-3-one
  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

文献信息

• A camphor-derived chiral auxiliary for hydroxyalkyl radicals
  作者：Philip Garner、Özge Şeşenoğlu、Hugh Burgoon

  DOI：10.1016/j.tetasy.2003.07.014

  日期：2003.10

  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.