5-(三氟甲基)吡喃-2-酮 | 76905-69-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 5-(三氟甲基)吡喃-2-酮
• 英文名称: 5-(trifluoromethyl)-2H-pyran-2-one
• 英文别名: 5-Trifluormethyl-2H-pyran-2-on；5-trifluoromethyl-2-pyrone；5-(trifluoromethyl)pyran-2-one
• CAS: 76905-69-6
• 化学式: C₆H₃F₃O₂
• 分子量: 164.084
• InChiKey: FNNWLFGGYITHAI-UHFFFAOYSA-N

物化性质

• 沸点：
  159.4±40.0 °C(Predicted)
• 密度：
  1.469±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(三氟甲基)吡喃-2-酮 在 硫酸 、 magnesium 、 lithium bromide 作用下， 以 丙酮 为溶剂， 反应 8.0h， 生成 3-苄基-5-(三氟甲基)-2-吡喃酮
  参考文献：
  名称：

  5-(Halomethyl)-2-pyranones as irreversible inhibitors of .alpha.-chymotrypsin

  摘要：

  A series of 5-(halomethyl)-2-pyranones were prepared and assayed as potential mechanism-based inhibitors of chymotrypsin, in order to test whether substitution of a suitable electron-withdrawing group at position 5 in a 2-pyranone can activate the ring for catalytic hydrolysis, as well as form a mechanism-based inhibitor. 3-Benzyl-5-(chloromethyl)-2-pyranone (3) and 3-(1-naphthylmethyl)-5-(chloromethyl)-2-pyranone (4) rapidly and irreversibly inactivate chymotrypsin with high efficiency (I/E = 2.0 for 3 and 1.38 for 4). However, evidence for their formation of an acyl enzyme is lacking, and thus they may simply be active-site alkylating agents. 6-Methyl substitution on 4, or replacement of the chloromethyl of 3 with CF3, prevents inactivation. Since 6-bromo substitution is capable of ring activation, but 5-bromo substitution (3-benzyl-5-bromo-2-pyranone (11)) is not, the 5-position of the pyrone does not appear to affect catalytic hydrolysis.

  DOI：

  10.1021/jm00158a027

文献信息

• Cycloaddition of 2H-Pyran-2-thiones with Nitroso Derivatives. An Unexpected Cycloaddition-Rearrangement Reaction
  作者：Albert Defoin、G�rard Augelmann、Hans Fritz、Guillaume Geffroy、Christian Schmidlin、Jacques Streith

  DOI：10.1002/hlca.19850680724

  日期：1985.11.13

  Reaction of pyran-2-thiones 4 with nitroso derivatives led surprisingly to type-8 (19) adducts which proved to be isomeric with the initially expected primary Diels-Alder cycloadducts 5. Methyl 2-thioxo-2H-pyran-5-carboxylate (4f), when reacted with nitrosobenzene at -10°, led quantitatively to the thieto-oxazine intermediate 13, which turned out to be the cornerstone of the complex cycloaddition-rearrangement

  吡喃-2-硫酮的反应4与导致令人惊奇的亚硝基衍生物型- 8（19被证明是同分异构体与最初的预期主要）加合物狄尔斯-阿尔德cycloadducts 5。当在-10°下与亚硝基苯反应时，2-thioxo-2 H -pyran-5-羧酸甲酯（4f）定量地导致硫代恶嗪中间体13转化为复杂的环加成重排5 的基石。8个反应途径（方案3）。差示扫描量热法，与18a 19a相同转化，被允许证明该多步重排总体上是高温放热过程，最终产物19代表沿着该反应路径的能量吸收器。
• Synthese von 2(1<i>H</i>)-Pyridonen aus 2<i>H</i>-Pyran-2-onen
  作者：Vratislav Kvita

  DOI：10.1055/s-1991-26600

  日期：——

  Synthesis of 2(1H)-Pyridones From 2H-Pyran-2-ones 5-Substituted and 4,5-disubstituted 2(1H)-pyridones (13 examples) with formyl, acyl, alkoxycarbonyl, and trifluoromethyl groups in the 5 position were prepared in 16-97% yield by amination of the corresponding 2H-pyran-2-ones with hexamethyldisilazane or alkyl(trimethylsilyl)amines.

  从2H-吡喃-2-酮合成2(1H)-吡啶酮 5-取代和4,5-二取代的2(1H)-吡啶酮（13个例子）通过将相应的2H-吡喃-2-酮与六甲基二硅氨或烷基（ trimethylsilyl）胺进行胺化反应，在16%-97%的收率下制备了具有甲醛基、酰基、烷氧羧基和三氟甲基的5位取代基。
• Process for the preparation of electroactive Langmuir-Blodgett layer
  申请人：Ciba-Geigy Corporation

  公开号：US04940516A1

  公开（公告）日：1990-07-10

  A process for the preparation of Langmuir-Blodgett layer systems is described. The process comprises transferring a monolayer to a solid substrate having an electrically conductive surface by applying an electric potential, thereby oxidizing or reducing an electroactive molecule present in the monolayer. The layer systems so obtained can be used, for example, as electrically conductive layers or as sensors.

  本发明描述了一种制备Langmuir-Blodgett层系统的方法。该方法包括通过施加电位将单分子层转移至具有电导表面的固体基板上，从而氧化或还原单分子层中存在的电活性分子。所获得的层系统可以用作电导层或传感器等用途。
• Process for making 5-trifluoromethyl pyridone
  申请人：Reilly Tar & Chemical Corp.

  公开号：US04230864A1

  公开（公告）日：1980-10-28

  The chemical compound 5-trifluoromethyl-2-pyrone and a process for preparing a 5-trifluoromethyl-2-oxy compound of the formula ##STR1## wherein A is oxygen or nitrogen bearing a hydrogen, comprising the step of reacting an amount of the 5-carboxy precursor of the compound with a suitable fluorinating agent to selectively transform the 5-carboxy group without altering the oxygen function in the 2-position of the ring.

  化学物质5-三氟甲基-2-吡酮及其制备5-三氟甲基-2-氧化物的过程，该化合物的式子为##STR1##其中A是带有氢的氧或氮，包括以下步骤：将化合物的5-羧基前体与适当的氟化剂反应，以选择性转化5-羧基团，而不改变环的2位的氧功能。
• Electroactive ultra-thin layers
  申请人：Ciba-Geigy Corporation

  公开号：US05108841A1

  公开（公告）日：1992-04-28

  Monolayer or multilayer systems containing compounds of the formula I ##STR1## in which X is S or Se, R.sup.1 is C.sub.1 --C.sub.30 alkyl, --CF.sub.3, --O--R.sup.3, --S--R.sup.3 or --CO--O--R.sup.3, R.sup.2 is hydrogen, C.sub.1 --C.sub.30 alkyl, --CF.sub.3, --O--R.sup.3 or --CO--O--R.sup.3, and R.sup.3 is C.sub.1 --C.sub.30 alkyl or partially or perfluorinated C.sub.1 --C.sub.30 alkyl, are described. Electrically conductive layers which are suitable, for example, for the production of electrically conductive coatings can be prepared from the layer systems by doping with electron acceptors.

  本发明涉及一种包含式I的化合物的单层或多层系统：##STR1## 其中X是S或Se，R1是C1-C30烷基，-CF3，-O-R3，-S-R3或-CO-O-R3，R2是氢，C1-C30烷基，- ，-O-R3或-CO-O-R3，R3是C1-C30烷基或部分或全氟化的C1-C30烷基。通过掺杂电子受体，可以从该层系统制备适用于制备电导涂层的导电层。