2,2-difluoro-5-methyl-1-p-tolylhex-4-en-1-one | 239473-10-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-difluoro-5-methyl-1-p-tolylhex-4-en-1-one
• CAS: 239473-10-0
• 化学式: C₁₄H₁₆F₂O
• 分子量: 238.277
• InChiKey: ATURNLKHCYPVQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  亚甲基三苯基膦烷 、 2,2-difluoro-5-methyl-1-p-tolylhex-4-en-1-one 以 乙醚 为溶剂， 以51%的产率得到3,3-difluoro-6-methyl-2-p-tolylhepta-1,5-diene
  参考文献：
  名称：

  Convergent synthesis of fluoro and gem-difluoro compounds using trifluoromethyltrimethylsilane

  摘要：

  Trifluorotrimethylsilane reacts with acylsilanes to give the corresponding difluoroenoxysilanes via the Brook rearrangement of the alcoholate adducts. The difluoroenoxysilane reacts in situ with various types of electrophilic substrates, leading to gem-difluoro functionalized derivatives in a one-pot methodology. This paper describes reactions with Michael accepters, prenyl, benzyl and glycosyl donors leading to 2,2-difluoro-1,5-diketones, 4,4- or 6,6-difluorocyclohexenones, o- or p-fluorophenols, difluoro analogues of terpenes, and difluoro-C-glycosides. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(99)00158-x
• 作为产物：
  描述：

  trimethyl-4-methylbenzoylsilane 在 DFTPS zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 生成 2,2-difluoro-5-methyl-1-p-tolylhex-4-en-1-one
  参考文献：
  名称：

  Convergent synthesis of fluoro and gem-difluoro compounds using trifluoromethyltrimethylsilane

  摘要：

  Trifluorotrimethylsilane reacts with acylsilanes to give the corresponding difluoroenoxysilanes via the Brook rearrangement of the alcoholate adducts. The difluoroenoxysilane reacts in situ with various types of electrophilic substrates, leading to gem-difluoro functionalized derivatives in a one-pot methodology. This paper describes reactions with Michael accepters, prenyl, benzyl and glycosyl donors leading to 2,2-difluoro-1,5-diketones, 4,4- or 6,6-difluorocyclohexenones, o- or p-fluorophenols, difluoro analogues of terpenes, and difluoro-C-glycosides. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(99)00158-x

文献信息

• Mixed organofluorine-organosilicon chemistry. 10. Allylation and benzylation of difluoroenoxysilanes. Application to the synthesis of gem -difluoroterpene analogues
  作者：Olivier Lefebvre、Thierry Brigaud、Charles Portella

  DOI：10.1016/s0040-4020(99)00348-8

  日期：1999.6

  Acylsilane and trifluoromethyltrimethylsilane gave, under fluoride initiation, a difluoroenoxysilane which is used in situ in a Lewis add catalyzed coupling with a prenyl ester or a benzylic bromide. The advantage of this one-pot procedure was illustrated by its use in the synthesis of gcm-difluoro analogues of terpenes (dehydro-or-curcumene and or-turmerone). (C) 1999 Elsevier Science Ltd. All rights reserved.