4-(dimethylamino)-1,1,1-trifluorobut-3-en-2-one | 142503-25-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(dimethylamino)-1,1,1-trifluorobut-3-en-2-one
• 英文别名: 3-Buten-2-one, 4-(dimethylamino)-1,1,1-trifluoro-, (3E)-
• CAS: 142503-25-1
• 化学式: C₆H₈F₃NO
• mdl: MFCD00764476
• 分子量: 167.131
• InChiKey: OPFMBYIQGSJDOB-UHFFFAOYSA-N

物化性质

• 沸点：
  103.4±40.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-噻吩基锂 、 4-(dimethylamino)-1,1,1-trifluorobut-3-en-2-one 以 四氢呋喃 为溶剂， 以51%的产率得到(E)-1,1,1-trifluoro-4-(thiophen-2-yl)but-3-en-2-one
  参考文献：
  名称：

  Enantioselective reduction of α,β-unsaturated ketones bearing the trifluoromethyl group

  摘要：

  alpha,beta -Unsaturated ketones bearing the trifluoromethyl group were enantioselectively reduced by a variety of reagents to the corresponding secondary allylic alcohols with e.e. in the range 87-99%. The influence of the trifluoromethyl group on the enantioselectivity is discussed. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(01)00209-9
• 作为产物：
  描述：

  乙烯基乙醚 、 三氟乙酸酐 在 4-二甲氨基吡啶 二甲胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.67h， 生成 4-(dimethylamino)-1,1,1-trifluorobut-3-en-2-one
  参考文献：
  名称：

  Pyrazole-amides and sulfonamides as sodium channel modulators

  摘要：

  本发明的化合物调节哺乳动物中的PN3，并且在治疗哺乳动物的疼痛方面是有用的。

  公开号：

  US20040220170A1

文献信息

• [EN] HALOGEN SUBSTITUTED DIKETONES, PYRAZOLE COMPOUNDS AND PROCESSES FOR THE MANUFACTURE OF PYRAZOLE COMPOUNDS<br/>[FR] DICÉTONES SUBSTITUÉES PAR UN HALOGÈNE, COMPOSÉS DE PYRAZOLE ET LEURS PROCÉDÉS DE PRODUCTION
  申请人：SOLVAY

  公开号：WO2017129759A1

  公开（公告）日：2017-08-03

  The present invention concerns new halogen substituted diketone compounds, new pyrazole compounds, processes for the manufacture of pyrazole compounds and processes for the manufacture of agrochemical or pharmaceutical compounds.

  本发明涉及新的卤代二酮化合物、新的吡唑化合物、制造吡唑化合物的方法以及制造农用化学品或药物化合物的方法。
• One-Pot Sequential Multistep Transformation of α,β-Unsaturated Trifluoromethyl Ketones: Facile Synthesis of Trifluoromethylated 2-Pyridones
  作者：Fa-Guang Zhang、Jun-An Ma、Ning Lv、Yi-Qiang Tian

  DOI：10.1055/s-0037-1612077

  日期：2019.3

  A one-pot transformation of α,β-unsaturated trifluoromethyl ketones with 2-(phenylsulfinyl)acetamide to give trifluoromethylated 2-pyridones is realized. The reaction proceeds under mild conditions and involves multiple steps in an expeditious and controlled sequence to provide efficient access to a broad range of trifluoromethylated 2-pyridones in moderate to high yields. Moreover, further synthetic

  实现了α,β-不饱和三氟甲基酮与2-(苯基亚磺酰基)乙酰胺的一锅法转化，得到三氟甲基化的2-吡啶酮。该反应在温和的条件下进行，涉及多个步骤，以快速且受控的顺序进行，以提供以中等至高产率有效获取范围广泛的三氟甲基化 2-吡啶酮的途径。此外，进一步的合成操作允许以良好的效率常规合成各种三氟甲基化吡啶。
• Reaction of Push–Pull Enaminoketones and <i>in Situ</i> Generated <i>ortho</i>-Quinone Methides: Synthesis of 3-Acyl-4<i>H</i>-chromenes and 2-Acyl-1<i>H</i>-benzo[<i>f</i>]chromenes as Precursors for Hydroxybenzylated Heterocycles
  作者：Anton V. Lukashenko、Vitaly A. Osyanin、Dmitry V. Osipov、Yuri N. Klimochkin

  DOI：10.1021/acs.joc.6b02716

  日期：2017.2.3

  developed. The chromenes are presumably formed through an initial oxa-Diels–Alder reaction, followed by an elimination of amine. The possibility of further transformations of given chromenes to o-hydroxybenzylated pyrazoles, isoxazoles, and pyridines has been demonstrated.

  已经开发了一种简单有效的方法，可以由邻醌甲基化物前体和推挽式烯酮合成吡喃环中含有三氟乙酰基或芳酰基的4 H-苯二甲基和1 H-苯并[ f ]苯二甲基。苯并二氢吡喃酮可能是通过最初的Oxa-Diels-Alder反应形成，然后消除胺而形成的。已经证明给定的色烯进一步转化为邻羟基苄基化的吡唑，异恶唑和吡啶的可能性。
• Synthesis, effect of substituents on the regiochemistry and equilibrium studies of tetrazolo[1,5-<i>a</i>]pyrimidine/2-azidopyrimidines
  作者：Elisandra Scapin、Paulo R S Salbego、Caroline R Bender、Alexandre R Meyer、Anderson B Pagliari、Tainára Orlando、Geórgia C Zimmer、Clarissa P Frizzo、Helio G Bonacorso、Nilo Zanatta、Marcos A P Martins

  DOI：10.3762/bjoc.13.237

  日期：——

  An efficient synthesis methodology for a series of tetrazolo[1,5-a]pyrimidines substituted at the 5- and 7-positions from the cyclocondensation reaction [CCC + NCN] was developed. The NCN corresponds to 5-aminotetrazole and CCC to β-enaminone. Two distinct products were observed in accordance with the β-enaminone substituent. When observed in solution, the compounds can be divided into two groups: (a) precursor compounds with R = CF₃ or CCl₃, which leads to tetrazolo[1,5-a]pyrimidines in high regioselectivity with R at the 7-position of the heterocyclic ring; and (b) precursor compounds with R = aryl or methyl, which leads to a mixture of compounds, tetrazolo[1,5-a] pyrimidines (R in the 5-position of the ring) and 2-azidopyrimidines (R in the 4-position of the ring), which was attributed to an equilibrium of azide–tetrazole. In the solid state, all compounds were found as 2-azidopyrimidines. The regiochemistry of the reaction and the stability of the products are discussed on the basis of the data obtained by density functional theory (DFT) for energetic and molecular orbital (MO) calculations.

  开发了一种高效的合成方法，用于从环缩合反应[CCC + NCN]中取代在5-和7-位置的一系列噻唑并[1,5-a]嘧啶。其中，NCN对应于5-氨基四唑，CCC对应于β-烯酮。根据β-烯酮取代基，观察到了两种不同的产物。在溶液中观察时，这些化合物可以分为两组：(a) 前体化合物，其中R = CF3或CCl3，导致噻唑并[1,5-a]嘧啶在杂环环上的7-位置具有高区域选择性的R；和(b) 前体化合物，其中R = 芳基或甲基，导致一种混合物，即噻唑并[1,5-a]嘧啶（环上5-位置的R）和2-叠氮基嘧啶（环上4-位置的R），这归因于叠氮酸盐-四唑之间的平衡。在固态中，所有化合物都被发现为2-叠氮基嘧啶。基于密度泛函理论（DFT）和分子轨道（MO）计算所得的数据，讨论了反应的区域化学和产物的稳定性。
• Regiospecific Organocatalytic Asymmetric Aldol Reaction of Methyl Ketones and α,β-Unsaturated Trifluoromethyl Ketones
  作者：Xiao-Jin Wang、Yan Zhao、Jin-Tao Liu

  DOI：10.1021/ol070217z

  日期：2007.3.1

  [structure: see text]. The aldol reaction of methyl ketones and alpha,beta-unsaturated trifluoromethyl ketones occurred under mild conditions with the combination of proline-derived N-sulfonylamide and trifluoroacetic acid as the catalyst to give the corresponding unsaturated alpha-trifluoromethyl tertiary alcohols in high yields with good enatioselectivities.

  [结构：见文字]。甲基酮和α，β-不饱和三氟甲基酮的醛醇缩合反应在温和条件下发生，脯氨酸衍生的N-磺酰胺和三氟乙酸作为催化剂的结合，以高收率和良好的对映选择性得到相应的不饱和α-三氟甲基叔醇。 。