1-(4-Fluorophenyl)hex-2-yn-1-one | 1072835-12-1

• 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: 1-(4-Fluorophenyl)hex-2-yn-1-one
• CAS: 1072835-12-1
• 化学式: C₁₂H₁₁FO
• 分子量: 190.217
• InChiKey: VTBVPMRLSURPQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-Fluorophenyl)hex-2-yn-1-one 在 盐酸 、 水 、 sodium hydroxide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 2.0h， 生成 3-Amino-6-(4-fluorophenyl)-4-propylpyran-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 3-amino-2-pyrones as selective cyclooxygenase-1 (COX-1) inhibitors

  摘要：

  A group of 3-amino-2-pyrones were synthesized and their biological activities were evaluated for inhibiting cyclooxygenase (COX) activity. This study has led to the identification of COX-1-selective inhibitors. Among the tested compounds, the compound 5j exhibited the most potent COX-1 inhibitory activity (IC50 = 19.32 mu g/mL) and COX-1 selectivity index (SI = 41.98). (C) 2013 Qing-Fa Zhou. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.01.005
• 作为产物：
  描述：

  1-戊炔 在 Jones reagent 、 乙基溴化镁 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 16.0h， 生成 1-(4-Fluorophenyl)hex-2-yn-1-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 3-amino-2-pyrones as selective cyclooxygenase-1 (COX-1) inhibitors

  摘要：

  A group of 3-amino-2-pyrones were synthesized and their biological activities were evaluated for inhibiting cyclooxygenase (COX) activity. This study has led to the identification of COX-1-selective inhibitors. Among the tested compounds, the compound 5j exhibited the most potent COX-1 inhibitory activity (IC50 = 19.32 mu g/mL) and COX-1 selectivity index (SI = 41.98). (C) 2013 Qing-Fa Zhou. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.01.005

文献信息

• PPh₃-KOBu^t–Mediated Cyclization Reaction of <font>β</font>-Ketoesters with Alkynyl Ketones: Synthesis of Functionalized 2-Pyrones
  作者：Bin Hu、Ling-Guo Meng、Xiao-Li Hao、Mao Liang、Song Xue

  DOI：10.1080/00397911.2010.517374

  日期：2011.11.1

  Abstract Cyclization of alkynyl ketones with β-ketoesters mediated by PPh3 and KOBut to synthesize 2-pyrone derivatives was systematically described. A variety of β-ketoesters reacted with alkynyl ketones to give functionalized 2-pyrones in moderate to good yields under mild conditions.

  摘要 系统地描述了由 PPh3 和 KOBut 介导的炔基酮与 β-酮酯环化合成 2-吡喃酮衍生物。各种 β-酮酯与炔基酮反应，在温和条件下以中等至良好的产率得到官能化的 2-吡喃酮。
• Cycloaddition of Alkynyl Ketones with <i>N</i>-Tosylimines Catalyzed by Bu₃P and DMAP: Synthesis of Highly Functionalized Pyrrolidines and Azetidines
  作者：Ling-Guo Meng、Peijie Cai、Qingxiang Guo、Song Xue

  DOI：10.1021/jo801687v

  日期：2008.11.7

  Cycloadditions of alkynyl ketones with N-tosylimines catalyzed by Lewis bases to synthesize azetidines and pyrrolidines were systematically described. In the reaction of alkynyl ketones with N-tosylimines catalyzed by Bu3P at room temperature in toluene, highly functionalized pyrrolidines were formed in good to excellent yields. When DMAP was used in place of Bu3P as catalyst to facilitate the cycloaddition, completely substituted azetidines were produced in moderate to good yields in CH2Cl2. Both cyclization reactions proceeded smoothly with complete stereoselectivity. The scope and limitations of these cycloadditon reactions were also investigated.
• Synthesis and biological evaluation of 3-amino-2-pyrones as selective cyclooxygenase-1 (COX-1) inhibitors
  作者：Xue-Ping Chu、Qing-Fa Zhou、Shen Zhao、Fei-Fei Ge、Mian Fu、Jia-Peng Chen、Tao Lu

  DOI：10.1016/j.cclet.2013.01.005

  日期：2013.2

  A group of 3-amino-2-pyrones were synthesized and their biological activities were evaluated for inhibiting cyclooxygenase (COX) activity. This study has led to the identification of COX-1-selective inhibitors. Among the tested compounds, the compound 5j exhibited the most potent COX-1 inhibitory activity (IC50 = 19.32 mu g/mL) and COX-1 selectivity index (SI = 41.98). (C) 2013 Qing-Fa Zhou. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.