4,4,4-trifluoro-N-methoxy-N-methylbut-2-enamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4,4,4-trifluoro-N-methoxy-N-methylbut-2-enamide
• 英文别名: (E)-4,4,4-Trifluoro-N-methoxy-N-methyl-2-butenamide
• 化学式: C₆H₈F₃NO₂
• 分子量: 183.13
• InChiKey: SXKYBBUJTGYOIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 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：
  29.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,4,4-trifluoro-N-methoxy-N-methylbut-2-enamide 、 正己基锂 以73%的产率得到N-methoxy-N-methyl-3-(trifluoromethyl)nonanamide
  参考文献：
  名称：

  Synthesis of β-Trifluoromethylated Enones: An Unexpected Reactivity of Trifluoromethylated Weinreb Enamides towards Organolithium Species

  摘要：

  δ-三氟甲基化烯酮可通过四个步骤从三氟乙酰乙酸乙酯合成。关键的中间体是weinreb δ-三氟甲基化烯酰胺。

  DOI：

  10.1055/s-0029-1216748
• 作为产物：
  描述：

  C₇H₁₂F₃NO₅S 在 三乙胺 作用下， 生成 4,4,4-trifluoro-N-methoxy-N-methylbut-2-enamide
  参考文献：
  名称：

  Synthesis of β-Trifluoromethylated Enones: An Unexpected Reactivity of Trifluoromethylated Weinreb Enamides towards Organolithium Species

  摘要：

  δ-三氟甲基化烯酮可通过四个步骤从三氟乙酰乙酸乙酯合成。关键的中间体是weinreb δ-三氟甲基化烯酰胺。

  DOI：

  10.1055/s-0029-1216748

文献信息

• [EN] BICYCLIC JAK INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE JAK BICYCLIQUES ET LEURS UTILISATIONS
  申请人：INSILICO MEDICINE IP LTD

  公开号：WO2020198583A1

  公开（公告）日：2020-10-01

  Provided herein are compounds of Formulas (I), (II), (III), and (IV) and subformulas thereof, wherein the variables are defined herein. Also provided herein are pharmaceutical compositions comprising a compound of Formula (I), (II), (III), or (IV) and methods of using the compounds, e.g., in the treatment of immune disorders, inflammatory disorders, and cancer.

  本文提供了公式（I）、（II）、（III）和（IV）及其子公式的化合物，其中变量在此处定义。本文还提供了包括公式（I）、（II）、（III）或（IV）化合物的药物组合物，以及使用这些化合物的方法，例如用于治疗免疫紊乱、炎症性疾病和癌症。
• An Efficient and Safe Method for the Multigram Synthesis of trans-2-(Trifluoromethyl)cyclopropylamine
  作者：Oleg Lukin、Pavel Mykhailiuk、Vladimir Yarmolchuk、Andrii Bezdudny、Nataliya Tolmacheva、Alexander Boyko、Alexey Chekotylo、Andrei Tolmachev

  DOI：10.1055/s-0031-1289711

  日期：2012.4

  trans-2-(Trifluoromethyl)cyclopropylamine was prepared on a multigram scale from readily accessible 4,4,4-trifluorobut-2-enoic acid in five steps. The key step was a high-yielding cyclopropane ring formation from 4,4,4-trifluorobut-2-enoic acid methoxymethyl amide under Corey-Chaykovsky reaction conditions.

  trans-2-(三氟甲基)环丙胺通过五个步骤从易得的4,4,4-三氟丁-2-烯酸大规模制备，产量达到多克拉级别。关键步骤是在Corey-Chaykovsky反应条件下，从4,4,4-三氟丁-2-烯酸甲氧基甲基胺中高效生成环丙烷环。
• Chiral-at-Metal Rh(III) Complex-Catalyzed Michael Addition of Pyrazolones with α,β-Unsaturated 2-Acyl Imidazoles
  作者：Shi-Wu Li、Qian Wan、Qiang Kang

  DOI：10.1021/acs.orglett.8b00040

  日期：2018.3.2

  enantioselective conjugate addition of pyrazolones with α,β-unsaturated 2-acyl imidazoles catalyzed by chiral-at-metal rhodium complex is reported. The corresponding adducts were obtained in good yields (85%–96%) with excellent enantioselectivities (up to >99%). This protocol exhibits extraordinary reactivity, because of the fact that a complex with as little as 0.05 mol % Rh(III) can catalyze the title

  报道了吡唑酮与手性金属铑配合物催化的α，β-不饱和2-酰基咪唑的有效对映选择性共轭加成。以良好的对映选择性（高达> 99％）以良好的收率（85％–96％）获得了相应的加合物。由于具有低至0.05 mol％Rh（III）的络合物可以以优良的对映选择性在克级上催化标题反应，因此该方案具有非凡的反应性。
• Asymmetric (3+2) Cycloaddition Employing β‐Fluoroalkylated α,β‐Unsaturated 2‐Acyl Imidazole Catalyzed by a Chiral‐at‐Metal Rhodium Complex
  作者：Yujie Zhao、Xiang Ji、Xue Tian、Zhifei Zhao、Jixin Pian、Shi‐Wu Li

  DOI：10.1002/adsc.202301309

  日期：2024.4.9

  An asymmetric 1,3-dipolar cycloaddition of β-fluoroalkylated α,β-unsaturated 2-acyl imidazole with nitrones or N,N’-cyclic azomethine imines to construct chiral α-fluoroalkylated γ-amino alcohols or chiral α-fluoroalkylated 1,3-diamino compounds has catalyzed by chiral-at-metal rhodium complexes is reported. The corresponding products with three contiguous tertiary stereocenters were obtained in 62%-98%

  β-氟烷基化α,β-不饱和2-酰基咪唑与硝酮或N,N'-环状偶氮甲碱亚胺的不对称1,3-偶极环加成反应构建手性α-氟烷基化γ-氨基醇或手性α-氟烷基化1,3报道了手性金属铑配合物催化的二氨基化合物。获得具有三个连续三级立构中心的相应产物，产率为62%-98%，立体选择性高达>20:1 dr和99% ee。值得注意的是，低至 0.06 mol% 的手性金属铑络合物可以促进与硝酮或 N,N'-环状甲亚胺亚胺的克级反应。
• Direct Access to Highly Enantioenriched α-Branched Acrylonitriles through a One-Pot Sequential Asymmetric Michael Addition/Retro-Dieckmann/Retro-Michael Fragmentation Cascade
  作者：Nicolas Duchemin、Martin Cattoen、Oscar Gayraud、Silvia Anselmi、Bilal Siddiq、Roberto Buccafusca、Marc Daumas、Vincent Ferey、Michael Smietana、Stellios Arseniyadis

  DOI：10.1021/acs.orglett.0c02079

  日期：2020.8.7

  A highly enantioselective synthesis of alpha-branched acrylonitriles is reported featuring a one-pot sequential asymmetric Michael addition/retro-Dieckmann/retro-Michael fragmentation cascade. The method, which relies on a solid, bench-stable, and commercially available acrylonitrile surrogate, is practical, scalable, and highly versatile and provides a direct access to a wide range of enantioenriched nitrite-containing building blocks. Most importantly, the method offers a new tool to incorporate an acrylonitrile moiety in an asymmetric fashion.