4,4-difluoro-3-hydroxy-5-(methoxy)hexa-1,5-diene | 853730-19-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: 4,4-difluoro-3-hydroxy-5-(methoxy)hexa-1,5-diene
• 英文别名: 4,4-Difluoro-5-(2-methoxyethoxymethoxy)hexa-1,5-dien-3-ol
• CAS: 853730-19-5
• 化学式: C₁₀H₁₆F₂O₄
• 分子量: 238.231
• InChiKey: IMBXEKKNJQRQQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4-difluoro-3-hydroxy-5-(methoxy)hexa-1,5-diene 在 Hydroquinone 1,4-phthalazinediyl diether 、 甲基磺酰胺 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 氯化亚砜 、 sodium azide 、 potassium dioxotetrahydroxoosmate(VI) 、 potassium carbonate 、 三乙胺 、 三苯基膦 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 98.0h， 生成 (4R,5S)-5-(benzyloxycarbonylamino)methyl-3,3-difluoro-2-methyl-tetrahydrofuran-2,4-diol
  参考文献：
  名称：

  Highly Stereocontrolled Synthesis of gem-Difluoromethylenated Azasugars:  d- and l-1,4,6-Trideoxy-4,4-difluoronojirimycin

  摘要：

  D-1,4,6-Trideoxy-4,4-difluoronojirimycin and L-1,4,6-trideoxy-4,4-difluoronojirimycin, a novel series of gem-4,4-difluoromethylenated azasugars, were synthesized from CF3CH2OH in 10 steps. A key step was the highly diastereoselective construction of the piperidine ring via reductive amination.

  DOI：

  10.1021/ol050558h
• 作为产物：
  描述：

  3,3-Difluoro-2-(2-methoxy-ethoxymethoxy)-prop-2-en-1-ol 在 sodium hydroxide 、 四丁基硫酸氢铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 生成 4,4-difluoro-3-hydroxy-5-(methoxy)hexa-1,5-diene
  参考文献：
  名称：

  [2,3]-Wittig Rearrangements of Difluoroallylic Ethers. A Facile Entry to Highly Functionalized Molecules Containing a CF₂ Group

  摘要：

  Readily prepared primary, secondary, and tertiary difluoroallylic alcohols, derived from commercially available and inexpensive 2,2,2-trifluoroethanol, have been transformed into a range of difluoroallylic methyl ethers containing appropriate carbanion-stabilizing substituents. The [2,3]-Wittig rearrangements of these difluoroallylic ethers have been achieved cleanly, using lithium diisopropylamide in tetrahydrofuran at -30 degrees C, in excellent (secondary ether substrates) to good (primary and tertiary ether substrates) yields. Consequently, the approach allows convenient and rapid access to products containing a mid-chain CF2 group and with a useful level of functionality.

  DOI：

  10.1021/jo951516h

文献信息

• Synthesis and Biological Evaluation of Glycosidase Inhibitors:  <i>g</i><i>em</i>-Difluoromethylenated Nojirimycin Analogues
  作者：Ruo-Wen Wang、Xiao-Long Qiu、Mikael Bols、Fernando Ortega-Caballero、Feng-Ling Qing

  DOI：10.1021/jm060066q

  日期：2006.5.1

  In our ongoing program aimed at the design, synthesis, and biological evaluation of novel gem-difluoromethylenated glycosidase inhibitors, gem-4,4-difluoromethylenated iminosugars (5-9) were synthesized. The biological evaluation of these synthetic iminosugars showed that the gem-difluoromethylenyl group generally reduced the inhibition of glycosidases. However, this was not the case at pH 5.0, where

  在我们正在进行的旨在设计，合成和对新型宝石二氟甲基化糖苷酶抑制剂进行生物学评估的程序中，合成了gem-4,4-二氟甲基化亚氨基糖（5-9）。这些合成亚氨基糖的生物学评估表明，宝石-二氟亚甲基通常降低了糖苷酶的抑制作用。但是，在pH 5.0时不是这种情况，其中的宝石二氟甲基化亚氨基糖6是比同类亚氨基糖1和36更强的抑制剂，这表明该基团的影响主要是通过其对胺的作用。提出未质子化的亚氨基糖是优选与β-葡萄糖苷酶结合的物种，因为亚氨基糖6的pK（a）值低于1或36的pK（a）值，使亚氨基糖1和36在pH 5.0下大部分被质子化，而亚氨基糖6为不是。
• [2,3]-Wittig Rearrangements of Difluoroallylic Ethers. A Facile Entry to Highly Functionalized Molecules Containing a CF₂ Group
  作者：Sunita T. Patel、Jonathan M. Percy、Robin D. Wilkes

  DOI：10.1021/jo951516h

  日期：1996.1.1

  Readily prepared primary, secondary, and tertiary difluoroallylic alcohols, derived from commercially available and inexpensive 2,2,2-trifluoroethanol, have been transformed into a range of difluoroallylic methyl ethers containing appropriate carbanion-stabilizing substituents. The [2,3]-Wittig rearrangements of these difluoroallylic ethers have been achieved cleanly, using lithium diisopropylamide in tetrahydrofuran at -30 degrees C, in excellent (secondary ether substrates) to good (primary and tertiary ether substrates) yields. Consequently, the approach allows convenient and rapid access to products containing a mid-chain CF2 group and with a useful level of functionality.
• Highly Stereocontrolled Synthesis of <i>g</i><i>em</i>-Difluoromethylenated Azasugars:  <scp>d</scp>- and <scp>l</scp>-1,4,6-Trideoxy-4,4-difluoronojirimycin
  作者：Ruo-Wen Wang、Feng-Ling Qing

  DOI：10.1021/ol050558h

  日期：2005.5.1

  D-1,4,6-Trideoxy-4,4-difluoronojirimycin and L-1,4,6-trideoxy-4,4-difluoronojirimycin, a novel series of gem-4,4-difluoromethylenated azasugars, were synthesized from CF3CH2OH in 10 steps. A key step was the highly diastereoselective construction of the piperidine ring via reductive amination.