1,1,1-trifluoro-4-(1’-naphthyl)but-3-en-2-one | 1130233-67-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,1,1-trifluoro-4-(1’-naphthyl)but-3-en-2-one
• 英文别名: 1,1,1-trifluoro-4-naphthalen-1-ylbut-3-en-2-one
• CAS: 1130233-67-8
• 化学式: C₁₄H₉F₃O
• 分子量: 250.22
• InChiKey: QLUAALKEJCDJGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1,1,1-trifluoro-4-(1’-naphthyl)but-3-en-2-one 在 肼 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Novel pyrazoline derivatives as bi-inhibitor of COX-2 and B-Raf in treating cervical carcinoma

  摘要：

  Twenty four pyrazoline derivatives modified from Celecoxib were designed and synthesized as bi-inhibitor of COX-2 and B-Raf. They were evaluated for their COX-1/COX-2/B-Raf inhibitory and anti-proliferation activities. Compound A3 displayed the most potent activity against COX-2 and HeLa cell line (IC₅₀=0.008 μM; GI₅₀=19.86 μM) and showed superb COX-1/COX-2 selectivity (>500), being more potent and selective than positive control Celecoxib or 5-fluorouracil. Compounds A5 and B5 were introduced best B-Raf inhibitory activities (IC₅₀=0.15 μM and 0.12 μM, respectively). Compound A4 retained superb bioactivity against COX-2 and HeLa cell line (IC₅₀=0.015 μM; GI₅₀=23.82 μM) and displayed moderate B-Raf inhibitory activity (IC₅₀=3.84 μM). Docking simulation was conducted to give binding patterns. QSAR models were built using bioactivity data and optimized conformations to provide a future modification of COX-2/B-Raf inhibitors.

  DOI：

  10.1016/j.bmc.2014.05.059
• 作为产物：
  描述：

  1,1,1-三氟丙酮 、 1-萘甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 1,1,1-trifluoro-4-(1’-naphthyl)but-3-en-2-one
  参考文献：
  名称：

  Novel pyrazoline derivatives as bi-inhibitor of COX-2 and B-Raf in treating cervical carcinoma

  摘要：

  Twenty four pyrazoline derivatives modified from Celecoxib were designed and synthesized as bi-inhibitor of COX-2 and B-Raf. They were evaluated for their COX-1/COX-2/B-Raf inhibitory and anti-proliferation activities. Compound A3 displayed the most potent activity against COX-2 and HeLa cell line (IC₅₀=0.008 μM; GI₅₀=19.86 μM) and showed superb COX-1/COX-2 selectivity (>500), being more potent and selective than positive control Celecoxib or 5-fluorouracil. Compounds A5 and B5 were introduced best B-Raf inhibitory activities (IC₅₀=0.15 μM and 0.12 μM, respectively). Compound A4 retained superb bioactivity against COX-2 and HeLa cell line (IC₅₀=0.015 μM; GI₅₀=23.82 μM) and displayed moderate B-Raf inhibitory activity (IC₅₀=3.84 μM). Docking simulation was conducted to give binding patterns. QSAR models were built using bioactivity data and optimized conformations to provide a future modification of COX-2/B-Raf inhibitors.

  DOI：

  10.1016/j.bmc.2014.05.059

文献信息

• Per(poly)fluoroalkanesulfinamides assisted diastereoselective three-component inverse-electron-demand aza Diels–Alder reaction
  作者：Peng Li、Li-Juan Liu、Jin-Tao Liu

  DOI：10.1039/c0ob00699h

  日期：——

  A highly diastereoselective three-component inverse-electron-demand aza Diels–Alder reaction assisted by per(poly)fluoro-alkanesulfinamides is presented, providing a broad spectrum of highly functionalized piperidine derivatives with excellent endo/exo and facial diastereoselectivities. The electron-withdrawing perfluoroalkyl groups are crucial for the success of this reaction under mild conditions and facilitate monitoring the process and stereoselectivities of the reaction. The synthetic potential of these cycloadducts is also highlighted.

  报道了一种由全（多）氟烷基亚磺酰胺协助的高度立体选择性的三组分逆电子需求aza-Diels-Alder反应，提供了广泛的高度功能化的哌啶衍生物，具有优异的内型/外型和面立体选择性。吸电子的全氟烷基对于该反应在温和条件下的成功至关重要，并有助于监测反应过程和立体选择性。这些环加合物的合成潜力也得到了强调。
• 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。
• Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives
  作者：Shuyue Zhang、Mark D. Greenhalgh、Alexandra M. Z. Slawin、Andrew D. Smith

  DOI：10.1039/d0sc00432d

  日期：——

  An isothiourea-catalysed enantioselective synthesis of novel tetrahydroindolizine derivatives is reported through a one-pot tandem sequential process. The application of 2-(pyrrol-1-yl)acetic acid in combination with either a trifluoromethyl enone or an α-keto-β,γ-unsaturated ester in an enantioselective Michael addition–lactonisation process, followed by in situ ring-opening and cyclisation, led to

  通过一锅串联顺序过程报道了新型四氢吲哚嗪衍生物的异硫脲催化的对映选择性合成。在对映选择性迈克尔加成-内酯化过程中，将2-（吡咯-1-基）乙酸与三氟甲基烯酮或α-酮-β，γ-不饱和酯结合使用，然后进行原位开环和环化，导致一系列24种四氢吲哚嗪衍生物包含三个立体中心，其最大> 95：5 dr和> 99：1 er。
• Tandem stereoselective synthesis of new trifluoromethylated pyranopyrazoles
  作者：Jian Wang、Guan-Bo Huang、Li-Jun Yang、Feng Li、Jing Nie、Jun-An Ma

  DOI：10.1016/j.jfluchem.2014.10.008

  日期：2015.3

  trifluoromethyl ketones is described. The notable features of this tandem process are its operational simplicity, easily accessible starting materials, and mild reaction conditions. The corresponding trifluoromethylated pyranopyrazoles were obtained in excellent yields (85–99%) with good to excellent diastereoselectivities (6:1–30:1). In addition, the stereochemical assignment of the major isomer by X-ray crystallographic

  描述了吡唑啉酮与α，β-不饱和三氟甲基酮的有效串联迈克尔加成/芳构化/环化反应。该串联方法的显着特征是操作简单，易于获得的起始原料以及温和的反应条件。相应的三氟甲基化吡喃并吡咯类化合物的收率很高（85–99％），非对映选择性很好（6：1–30：1）。另外，通过X射线晶体学分析对主要异构体的立体化学分配表明主要形成反式产物。
• Quinidine‐Catalysed Enantioselective Synthesis of 6‐ and 4‐Trifluoromethyl‐Substituted Dihydropyrans
  作者：Kevin Kasten、David B. Cordes、Alexandra M. Z. Slawin、Andrew D. Smith

  DOI：10.1002/ejoc.201600583

  日期：2016.7

  The authors thank the Royal Society for a University Research Fellowship (ADS) and the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013), ERC Grant Agreement No. 279850 (KK), the authors also thank the EPSRC UK National Mass Spectrometry Facility at Swansea University.

  作者感谢皇家学会提供的大学研究奖学金 (ADS) 和欧盟第七框架计划 (FP7/2007-2013) 下的欧洲研究理事会，ERC 赠款协议编号 279850 (KK)，作者还感谢 EPSRC斯旺西大学的英国国家质谱设施。