4,4,4-trifluoro-1-(naphthalen-2-yl)butan-1-one | 1478296-30-8

• 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: 4,4,4-trifluoro-1-(naphthalen-2-yl)butan-1-one
• 英文别名: 2-Naphthyl 3,3,3-trifluoropropyl ketone；4,4,4-trifluoro-1-naphthalen-2-ylbutan-1-one
• CAS: 1478296-30-8
• 化学式: C₁₄H₁₁F₃O
• mdl: MFCD20084410
• 分子量: 252.236
• InChiKey: JBLOHIUIGBIZML-UHFFFAOYSA-N

物化性质

• 熔点：
  88-90 °C
• 沸点：
  320.3±42.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.214
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-萘甲酸甲酯 在 titanium(IV) isopropylate 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 生成 4,4,4-trifluoro-1-(naphthalen-2-yl)butan-1-one
  参考文献：
  名称：

  Copper-catalysed ring-opening trifluoromethylation of cyclopropanols

  摘要：

  在温和的反应条件下，开发了铜催化的环丙醇的环开放三氟甲基化反应。得到了多种合成有用的β-三氟甲基酮。

  DOI：

  10.1039/c5ob00808e

文献信息

• Synthesis of β-Trifluoromethylated Ketones from Propargylic Alcohols by Visible Light Photoredox Catalysis
  作者：Sehyun Park、Jung Min Joo、Eun Jin Cho

  DOI：10.1002/ejoc.201500031

  日期：2015.7

  A practical method to access β-trifluoromethyl ketones from readily available propargylic alcohols by visible light photocatalysis has been developed. Trifluoromethylation of propargylic alcohols with CF3I in the presence of Ru(bpy)3Cl2 as the photocatalyst followed by double-bond migration/keto-enol tautomerization provides β-trifluoromethyl ketones as the final product.

  远程位置的区域选择性三氟甲基化代表了生物活性分子和功能材料开发的重要挑战。已经开发出一种通过可见光光催化从容易获得的炔丙醇中获取 β-三氟甲基酮的实用方法。在作为光催化剂的 Ru(bpy)3Cl2 存在下，用 CF3I 对炔丙醇进行三氟甲基化，然后进行双键迁移/酮-烯醇互变异构，得到 β-三氟甲基酮作为最终产物。
• Boron-trihalide-promoted regioselective ring-opening reactions of gem-difluorocyclopropyl ketones
  作者：Tang-Po Yang、Qiang Li、Jin-Hong Lin、Ji-Chang Xiao

  DOI：10.1039/c3cc47879c

  日期：——

  Boron trihalide-promoted ring-opening reactions of gem-difluorocyclopropyl ketones to give the corresponding β-trifluoromethyl ketones and β-halodifluoromethyl ketones were described. It was found that boron trihalides act as both Lewis acids and nucleophiles and the proximal bond prefers to cleave in this transformation.

  描述了硼三卤化物促进的gem-二氟环丙酮开环反应，以生成相应的β-三氟甲基酮和β-卤二氟甲基酮。研究发现，硼三卤化物既可以作为路易斯酸，也可以作为亲核试剂，并且在该转化中，靠近的键更倾向于断裂。
• Synthesis of β-CF3 Ketones through Copper/Silver Cocatalyzed Oxidative Coupling of Enol Acetates with ICH2CF3
  作者：Wei Deng、Jiannan Xiang、Niannian Yi、Yi Xiong、De Chen、Sheng Zeng、Chaozhihui Cheng、Pengjie Wang

  DOI：10.1055/s-0037-1610257

  日期：2018.10

  A simple method for the synthesis of β-CF3 ketones through copper/silver cocatalyzed oxidative coupling of enol acetates with ICH2CF3 has been developed. Enol acetates were chosen as the source of carbonyl group, giving the β-CF3 ketones in moderate yields. Control experiments imply that a radical process maybe involved in this reaction.

  开发了一种通过铜/银共催化氧化偶联烯醇乙酸酯与 ICH2 合成 β-CF3 酮的简单方法。选择烯醇乙酸酯作为羰基的来源，得到中等产率的 β- 酮。对照实验表明该反应可能涉及一个自由基过程。
• Oxidative 3,3,3-trifluoropropylation of arylaldehydes
  作者：Akari Ikeda、Masaaki Omote、Shiho Nomura、Miyuu Tanaka、Atsushi Tarui、Kazuyuki Sato、Akira Ando

  DOI：10.3762/bjoc.9.279

  日期：——

  A reaction between (E)-trimethyl(3,3,3-trifluoroprop-1-en-1-yl)silane (1) and arylaldehydes 2 was triggered by fluoride anions to afford aryl 3,3,3-trifluoropropyl ketones 3 in moderate to good yield. A mechanistic study of this reaction indicated that it occurred via an allyl alkoxide (4). A subsequent 1,3-proton shift of the benzylic proton of 4 forms 3. This reaction involves oxidative 3,3,3-trifluoropropylation of an arylaldehyde to afford 4,4,4-trifluoro-1-arylbutan-1-one.

  使用氟化物阴离子引发(E)-三甲基(3,3,3-三氟丙-1-烯-1-基)硅烷(1)和芳基醛(2)之间的反应，以中等到良好的产率得到芳基3,3,3-三氟丙基酮(3)。对该反应的机理研究表明，它通过烯丙基醇盐(4)发生。随后，4的苄基质子发生1,3-质子迁移形成3。该反应涉及芳基醛的氧化性3,3,3-三氟丙基化，以得到4,4,4-三氟-1-芳基丁酮。
• Copper/Silver Cocatalyzed Oxidative Coupling of Vinylarenes with ICH₂CF₃ or ICH₂CHF₂ Leading to β-CF₃/CHF₂-Substituted Ketones
  作者：Niannian Yi、Hao Zhang、Chonghui Xu、Wei Deng、Ruijia Wang、Dongming Peng、Zebing Zeng、Jiannan Xiang

  DOI：10.1021/acs.orglett.6b00498

  日期：2016.4.15

  A novel copper/silver cocatalyzed oxidative coupling of vinylarenes with ICH2CF3 or ICH2CHF2 through a radical process has been developed. The transformation provides an attractive approach to beta-CF3/CHF2-substituted ketones, with the advantages of easily available starting materials and operational simplicity.