3,3-difluoro-4-hydroxy-4-phenyl-2-butanone | 119352-47-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,3-difluoro-4-hydroxy-4-phenyl-2-butanone
• 英文别名: 3,3-difluoro-4-hydroxy-4-phenylbutan-2-one；1-Phenyl-1-hydroxy-2,2-difluoro-3-butanone
• CAS: 119352-47-5
• 化学式: C₁₀H₁₀F₂O₂
• 分子量: 200.185
• InChiKey: WBLDNIKXQYVACL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3-difluoro-4-hydroxy-4-phenyl-2-butanone 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 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 20.75h， 生成 (Z)-4,4-difluoro-5-hydroxy-3-methyl-5-phenylpent-2-enoic acid
  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：

  2,2-difluoro-1-phenyl-3-(phenylthio)but-3-en-1-ol 在 mercury dichloride 作用下， 以 三氟乙酸 为溶剂， 反应 10.0h， 以61%的产率得到3,3-difluoro-4-hydroxy-4-phenyl-2-butanone
  参考文献：
  名称：

  Allylation Of Novel β-Phenylthio Substituted gem-Difluoroallylic Bromide to Carbonyl Compounds

  摘要：

  The reaction of beta-phenylthio substituted gem-difluoroallylic bromide 3 with aldehydes and ketones in the presence of Zn(Cu) in THF at reflux temperature afforded the corresponding homoallylic alcohols 4 in good yields.

  DOI：

  10.1080/00397919908085762

文献信息

• Hepatitis C Virus Inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：US20130183269A1

  公开（公告）日：2013-07-18

  The present disclosure is generally directed to antiviral compounds, and more specifically directed to combinations of compounds which can inhibit the function of the NS5A protein encoded by Hepatitis C virus (HCV), compositions comprising such combinations, and methods for inhibiting the function of the NS5A protein.

  本公开涉及抗病毒化合物，更具体地涉及能够抑制丙型肝炎病毒（HCV）编码的NS5A蛋白功能的化合物组合，包括这种组合的组成物，以及抑制NS5A蛋白功能的方法。
• α,α-Difluoro-α-(trimethylsilyl)acetamides as Versatile Reagents for the Preparation of Difluorinated Aldol and Mannich Adducts
  作者：Aurélien Honraedt、Arie Van Der Lee、Jean-Marc Campagne、Eric Leclerc

  DOI：10.1002/adsc.201700371

  日期：2017.8.17

  The very efficient addition of α,α‐difluoro‐α‐(trimethylsilyl)acetamides to aldehydes, ketones and N‐(tert‐butanesulfinyl)imines is described. The reaction is promoted by a catalytic amount of tetra‐n‐butylammonium diphenyltrifluorosilicate (TBAT) and high yields, as well as very high stereoselectivities in the case of N‐(tert‐butanesulfinyl)imines, are achieved. The synthetic potential of this method

  描述了非常有效地将α，α-二氟-α-（三甲基甲硅烷基）乙酰胺添加到醛，酮和N-（叔丁烷亚磺酰基）亚胺中。催化量的四苯基三氟硅酸四正丁基铵（TBAT）促进了反应，并获得了高收率，并且在N-（叔丁烷亚磺酰基）亚胺的情况下实现了很高的立体选择性。通过添加各种格氏试剂或还原酰胺部分，将所得产物转化为β-羟基酮，二醇和β-氨基醇，说明了该方法的合成潜力。
• 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。
• Fluorine-containing organozinc reagents. IV.
  作者：Robert W Lang、Bruno Schaub

  DOI：10.1016/0040-4039(88)85053-6

  日期：1988.1

  Chlorodifluoroacetic acid has shown to be a promising starting material for Reformatskii-type syntheses of fluorine-containing molecules and thus, it offers an attractive extension to what is known from rather expensive bromodifluoroacetic acid.

  氯二氟乙酸已被证明是用于含氟分子的Reformatskii型合成的有前途的原料，因此，它提供了对相当昂贵的溴代二氟乙酸所具有的吸引力的扩展。
• Preparation of optically active α,α-difluoro-β-hydroxyketones
  作者：Katsuhiko Iseki、Daisuke Asada、Yoshichika Kuroki

  DOI：10.1016/s0022-1139(99)00033-0

  日期：1999.7

  The stereoselective synthesis of α,α-difluoro-β-hydroxyketones of high enantiomeric purity is described starting from optically active α,α-difluoro-β-hydroxy esters. The esters were converted to the corresponding N-methoxy-N-methyl amides, which were treated with Grignard and organolithium reagents to provide the α,α-difluoro-β-hydroxyketones with up to 100% ee.

  从光学活性的α，α-二氟-β-羟基酯开始描述了高对映体纯度的α，α-二氟-β-羟基酮的立体选择性合成。将酯转化为相应的N-甲氧基-N-甲基酰胺，将其用格利雅（Grignard）和有机锂试剂处理，以提供具有高达100％ee的α，α-二氟-β-羟基酮。