3,3-difluoro-4-hydroxy-4-(4-methoxyphenyl)butan-2-one | 1015236-52-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,3-difluoro-4-hydroxy-4-(4-methoxyphenyl)butan-2-one
• 英文别名: 3,3-Difluoro-4-hydroxy-4-(4-methoxyphenyl)butan-2-one
• CAS: 1015236-52-8
• 化学式: C₁₁H₁₂F₂O₃
• 分子量: 230.211
• InChiKey: ATCKWNJMPPSWLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,3-difluoro-4-hydroxy-4-(4-methoxyphenyl)butan-2-one 在 2,6-二甲基吡啶 、 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 18.75h， 生成 (Z)-methyl 4,4-difluoro-5-hydroxy-3-methyl-5-(4-methoxyphenyl)pent-2-enoate
  参考文献：
  名称：

  Fluoroallylboration−Olefination for the Synthesis of (Z)-4,4-Difluoropent-2-enoates and 5,5-Difluoro-5,6-dihydropyran-2-ones

  摘要：

  Horner-Wadsworth Emmons (HWE) or Still-Gennari olefination of TBS-protected 3,3-difluoro-4-hydroxy-2-ones, derived from the difluoroallylboration of aldehydes, provides the Z-isomer of 4,4,-difluoropent-2-enoates. These, upon hydrolysis, followed by Yamaguchi cyclization, afford 5,5-difluoro-4-methyl-5,6-dihydro-alpha-pyrones in high yields.

  DOI：

  10.1021/ol103097s
• 作为产物：
  描述：

  3-(benzyloxy)-2,2-difluoro-1-(4-methoxyphenyl)but-3-en-1-ol 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以75%的产率得到3,3-difluoro-4-hydroxy-4-(4-methoxyphenyl)butan-2-one
  参考文献：
  名称：

  Gem-Difluorinated Homoallyl Alcohols, β-Hydroxy Ketones, and syn- and anti-1,3-Diols via γ,γ-Difluoroallylboronates

  摘要：

  gamma,gamma-Difluoroallylboronates have been prepared from trifluoroethanol and utilized for the allylboration of a variety of aldehydes to provide gem-difluorinated homoallylic alcohols. alpha-Chiral aldehydes were allylborated in 4:1-13:1 diastereoselectivity favoring the anti-isomer. A representative series of difluorinated hydroxyl enol ethers were converted to the corresponding alpha,alpha-difluoro-beta-hydroxy ketones. Diastereoselective reduction of one of these to either syn- and anti-1,3-diol was also studied.

  DOI：

  10.1021/ol800069z

文献信息

• Brook/Elimination/Aldol Reaction Sequence for the Direct One-Pot Preparation of Difluorinated Aldols from (Trifluoromethyl)trimethylsilane and Acylsilanes
  作者：Mélanie Decostanzi、Jérémy Godemert、Sylvain Oudeyer、Vincent Levacher、Jean-Marc Campagne、Eric Leclerc

  DOI：10.1002/adsc.201500849

  日期：2016.2.18

  difluorinated aldols directly from Ruppert–Prakash reagent, acyltrimethylsilanes and aldehydes is reported. The process, initiated by a catalytic amount of an ammonium salt, involves the addition of (trifluoromethyl)trimethylsilane to the acylsilane, followed by a Brook rearrangement and elimination of a fluoride anion that promotes the subsequent aldol reaction. An efficient racemic reaction catalyzed

  据报道，有一种方法可以直接从Ruppert-Prakash试剂，酰基三甲基硅烷和醛一锅制备二氟羟醛。该过程由催化量的铵盐引发，涉及在酰基硅烷中添加（三氟甲基）三甲基硅烷，然后进行布鲁克重排，并消除促进后续羟醛反应的氟阴离子。描述了由四丁基三氟三苯基硅酸铵催化的高效外消旋反应，以及我们对不对称形式的首次尝试。
• <i>Gem</i>-Difluorinated Homoallyl Alcohols, β-Hydroxy Ketones, and <i>syn</i>- and <i>anti</i>-1,3-Diols via γ,γ-Difluoroallylboronates
  作者：P. Veeraraghavan Ramachandran、Anamitra Chatterjee

  DOI：10.1021/ol800069z

  日期：2008.3.1

  gamma,gamma-Difluoroallylboronates have been prepared from trifluoroethanol and utilized for the allylboration of a variety of aldehydes to provide gem-difluorinated homoallylic alcohols. alpha-Chiral aldehydes were allylborated in 4:1-13:1 diastereoselectivity favoring the anti-isomer. A representative series of difluorinated hydroxyl enol ethers were converted to the corresponding alpha,alpha-difluoro-beta-hydroxy ketones. Diastereoselective reduction of one of these to either syn- and anti-1,3-diol was also studied.
• Fluoroallylboration−Olefination for the Synthesis of (<i>Z</i>)-4,4-Difluoropent-2-enoates and 5,5-Difluoro-5,6-dihydropyran-2-ones
  作者：P. Veeraraghavan Ramachandran、Agnieszka Tafelska-Kaczmarek、Kaumba Sakavuyi、Anamitra Chatterjee

  DOI：10.1021/ol103097s

  日期：2011.3.18

  Horner-Wadsworth Emmons (HWE) or Still-Gennari olefination of TBS-protected 3,3-difluoro-4-hydroxy-2-ones, derived from the difluoroallylboration of aldehydes, provides the Z-isomer of 4,4,-difluoropent-2-enoates. These, upon hydrolysis, followed by Yamaguchi cyclization, afford 5,5-difluoro-4-methyl-5,6-dihydro-alpha-pyrones in high yields.