(4S)-4-[chloro(difluoro)methyl]oxetan-2-one | 208248-61-7

• 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: (4S)-4-[chloro(difluoro)methyl]oxetan-2-one
• CAS: 208248-61-7
• 化学式: C₄H₃ClF₂O₂
• 分子量: 156.516
• InChiKey: YWQUFFOJVHDEHS-REOHCLBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-萘甲醚 、 (4S)-4-[chloro(difluoro)methyl]oxetan-2-one 在 三氯化铝 作用下， 反应 3.0h， 以48%的产率得到4-chloro-4,4-difluoro-3-hydroxy-1-(2-methoxynaphthyl)-1-butanone
  参考文献：
  名称：

  Preparation and use of novel (S)-β-chlorodifluoromethyl-β-propiolactone as a chiral fluorinated building block

  摘要：

  Novel chiral fluorinated building block, (S)-beta-chlorodifluoromethyl-beta-propiolactone with up to >99% ee was prepared using the Lewis acid catalyzed [2+2]cycloaddition of ketene with chlorodifluoroacetaldehyde followed by enzymatic resolution with a lipase. The lactone thus obtained readily underwent the Friedel-Crafts type acylation with aromatic compounds in the presence of a Lewis acid to afford the corresponding chiral beta-hydroxy aryl ketones in good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00240-3
• 作为产物：
  描述：

  乙烯酮 、 氯二氟乙醛 在 zinc(II) iodide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 (4S)-4-[chloro(difluoro)methyl]oxetan-2-one
  参考文献：
  名称：

  Preparation and use of novel (S)-β-chlorodifluoromethyl-β-propiolactone as a chiral fluorinated building block

  摘要：

  Novel chiral fluorinated building block, (S)-beta-chlorodifluoromethyl-beta-propiolactone with up to >99% ee was prepared using the Lewis acid catalyzed [2+2]cycloaddition of ketene with chlorodifluoroacetaldehyde followed by enzymatic resolution with a lipase. The lactone thus obtained readily underwent the Friedel-Crafts type acylation with aromatic compounds in the presence of a Lewis acid to afford the corresponding chiral beta-hydroxy aryl ketones in good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00240-3