(Z)-3-amino-4,4,4-trifluoro-1-(4-fluorophenyl)but-2-en-1-one

• 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: (Z)-3-amino-4,4,4-trifluoro-1-(4-fluorophenyl)but-2-en-1-one
• 英文别名: 3-amino-1-(4-fluorophenyl)-4,4,4-trifluoro-2-buten-1-one
• 化学式: C₁₀H₇F₄NO
• 分子量: 233.165
• InChiKey: BAAGFYYADMHGAG-UITAMQMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-(4-fluorophenyl)-3-(trifluoromethyl)isoxazole 在 (1R,2R)-(-)-N,N'-二甲基-1,2-环己二胺 、 copper diacetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 36.0h， 以95%的产率得到(Z)-3-amino-4,4,4-trifluoro-1-(4-fluorophenyl)but-2-en-1-one
  参考文献：
  名称：

  铜催化的异恶唑的还原环裂解：氟代烷基化的烯胺酮的合成及其在制备塞来昔布，德拉曲昔和马伐昔布中的应用

  摘要：

  我们已经发现了铜/二胺催化的新反应性，用于异恶唑的还原性环裂解，以生成氟代烷基化的烯胺酮。该方案的优点是使用可商购的试剂，易于设置，功能广泛，并且具有区域特异性，并且不存在脱氟和可还原官能团的还原。氟烷基化吡唑类药物（如塞来昔布，德拉可昔布和马vacoxib）的一步式区域选择性合成证明了其实用性。

  DOI：

  10.1021/acs.joc.0c02980

文献信息

• 1,5-diphenyl pyrazole compounds for treatment of inflammation
  申请人：G. D. Searle & Co.

  公开号：US05475018A1

  公开（公告）日：1995-12-12

  A class of 1,5-diphenyl pyrazoles is described for the treatment of inflammation, including treatment of pain and disorders such as arthritis. Compounds of particular interest are of Formula I ##STR1## wherein R.sup.1 is methylsulfonyl; wherein R.sup.2 is selected from --CF.sub.3, --CF.sub.2 Cl, --CF.sub.2 H, --CF.sub.2 CF.sub.3 and --CF.sub.2 CF.sub.2 CF.sub.3 ; and wherein R.sup.3 is fluoro or chloro; or a pharmaceutically-acceptable salt thereof.

  描述了一类1,5-二苯基吡唑类化合物，用于治疗炎症，包括治疗疼痛和关节炎等疾病。特别感兴趣的化合物为式I ##STR1## 其中R.sup.1为甲磺酰基；其中R.sup.2选自--CF.sub.3，--CF.sub.2 Cl，--CF.sub.2 H，--CF.sub.2 CF.sub.3和--CF.sub.2 CF.sub.2 CF.sub.3；其中R.sup.3为氟或氯；或其药用可接受盐。
• Synthesis and Antifungal Activity of β-Trifluoroalkyl Aminovinyl Ketone Derivatives
  作者：Gary Gellerman、Natali Pariente、Zahi Paz、Anat Shnaiderman、Oded Yarden

  DOI：10.1021/jf902190w

  日期：2009.9.23

  Ten beta-trifluoroalkyl aminovinyl ketone derivatives were synthesized, and their inhibitory effects on several phytopathogenic fungi, an oomycete and plants were assessed. The various compounds were fungitoxic at the 10-100 mu M range, with (Z)-3-amino-4,4,4-trifluoro-1-(4-chlorophenyl)but-2-en-1-one exhibiting the highest inhibitory effect on most of the test pathogens. Alternaria alternata and Neurospora crassa were the most tolerant and sensitive fungi to the compounds, respectively. We propose that (Z)-3-amino-4,4,4-trifluoro-1-phenylbut-2-en-1-one is the minimal structural requirement for a beta-trifluoroalkyl aminovinyl ketone fungitoxic derivative.
• US5475018A
  申请人：——

  公开号：US5475018A

  公开（公告）日：1995-12-12
• [EN] ANTIMICROBIAL COMPOUNDS AND COMPOSITIONS<br/>[FR] COMPOSÉS ANTIVIRAUX ET COMPOSITIONS ANTIVIRALES
  申请人：ARIEL UNIVERSITY RES AND DEV C

  公开号：WO2010055474A2

  公开（公告）日：2010-05-20

  Disclosed are antimicrobial compounds and compositions, the use of such compounds and compositions in the treatment of an infection by microbes and methods for treating an infection by microbes, for example of fungi and oomycetes.
• Copper-Catalyzed Reductive Ring-Cleavage of Isoxazoles: Synthesis of Fluoroalkylated Enaminones and Application for the Preparation of Celecoxib, Deracoxib, and Mavacoxib
  作者：Chao Wan、Jian-Yu Pang、Wei Jiang、Xiao-Wei Zhang、Xiang-Guo Hu

  DOI：10.1021/acs.joc.0c02980

  日期：2021.3.19

  ring-cleavage of isoxazoles to yield fluoroalkylated enaminones. This protocol has the advantage of using commercially available reagents, ease of setting up, broad tolerance of functionality, and is regiospecific and free of defluorination and reduction of reducible functional groups. The utility was demonstrated by a one-step, regioselective synthesis of fluoroalkylated pyrazole-based drugs such as celecoxib

  我们已经发现了铜/二胺催化的新反应性，用于异恶唑的还原性环裂解，以生成氟代烷基化的烯胺酮。该方案的优点是使用可商购的试剂，易于设置，功能广泛，并且具有区域特异性，并且不存在脱氟和可还原官能团的还原。氟烷基化吡唑类药物（如塞来昔布，德拉可昔布和马vacoxib）的一步式区域选择性合成证明了其实用性。