6-(5-chloro-2,2,3,3,4,4,5,5-octafluoro-pentyl)-3-oxa-bicyclo[3.2.1]octan-2-one

• 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: 6-(5-chloro-2,2,3,3,4,4,5,5-octafluoro-pentyl)-3-oxa-bicyclo[3.2.1]octan-2-one
• 化学式: C₁₂H₁₁ClF₈O₂
• 分子量: 374.658
• InChiKey: FRKUNDINIRTTOC-LYFYHCNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  丙戊酸相关物质A 、 1-氯-6-碘全氟己烷 在 sodium dithionite 、 碳酸氢钠 、 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 6.0h， 以89%的产率得到6-(5-chloro-2,2,3,3,4,4,5,5-octafluoro-pentyl)-3-oxa-bicyclo[3.2.1]octan-2-one
  参考文献：
  名称：

  Stereoselective cycloaddition–lactonization reaction of 2-allyl-4-pentenoic acids with polyfluoroalkyl iodides. An efficient synthesis of polyfluoroalkyl-containing bicyclolactone derivatives

  摘要：

  Polyfluoroalkyl-containing bicyclolactones were synthesized via the sodium dithionite-initiated cyclo-addition lactonization reaction of 2-allyl-4-pentenoic acids and polyfluoroalkyl iodides. The chemo- and stereo-selectivity of the cycloaddition lactonization reaction strongly depended on the space hindrance of 2-substituent in 2-allyl-4-pentenoic acids. The reaction was believed to proceed through a tandem free radical addition-lactonization process. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.002

文献信息

• Stereoselective cycloaddition–lactonization reaction of 2-allyl-4-pentenoic acids with polyfluoroalkyl iodides. An efficient synthesis of polyfluoroalkyl-containing bicyclolactone derivatives
  作者：Xueyan Yang、Xianjin Yang、Wei Pan、Ying Wang、Wei Cai、Fanhong Wu

  DOI：10.1016/j.tet.2010.07.002

  日期：2010.9

  Polyfluoroalkyl-containing bicyclolactones were synthesized via the sodium dithionite-initiated cyclo-addition lactonization reaction of 2-allyl-4-pentenoic acids and polyfluoroalkyl iodides. The chemo- and stereo-selectivity of the cycloaddition lactonization reaction strongly depended on the space hindrance of 2-substituent in 2-allyl-4-pentenoic acids. The reaction was believed to proceed through a tandem free radical addition-lactonization process. (C) 2010 Elsevier Ltd. All rights reserved.