3-(4-Bromophenyl)-5-prop-2-ynyl-6,7-dihydro-[1,2]oxazolo[4,5-c]pyridin-4-one | 1365759-08-5

• 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: 3-(4-Bromophenyl)-5-prop-2-ynyl-6,7-dihydro-[1,2]oxazolo[4,5-c]pyridin-4-one
• CAS: 1365759-08-5
• 化学式: C₁₅H₁₁BrN₂O₂
• 分子量: 331.169
• InChiKey: GCAINLWXGHYMRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-叠氮-4-氯苯 、 3-(4-Bromophenyl)-5-prop-2-ynyl-6,7-dihydro-[1,2]oxazolo[4,5-c]pyridin-4-one 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以74%的产率得到3-(4-Bromophenyl)-5-[[1-(4-chlorophenyl)triazol-4-yl]methyl]-6,7-dihydro-[1,2]oxazolo[4,5-c]pyridin-4-one
  参考文献：
  名称：

  Isoxazolodihydropyridinones: 1,3-Dipolar Cycloaddition of Nitrile Oxides onto 2,4-Dioxopiperidines

  摘要：

  Practical and efficient methods have been developed for the diversity-oriented synthesis of isoxazolodihydropyridinones via the 1,3-dipolar cycloaddition of nitrile oxides onto 2,4-dioxopiperidines. A select few of these isoxazolodihydropyridinones were further elaborated with triazoles by copper-catalyzed azide-alkyne cycloaddition reactions. A total of 70 compounds and intermediates were synthesized and analyzed for drug likeness. Sixty-four of these novel compounds were submitted to the NIH Molecular Libraries Small Molecule Repository for high-throughput biological screening.

  DOI：

  10.1021/co200200u
• 作为产物：
  描述：

  Tert-butyl 3-(4-bromophenyl)-4-oxo-6,7-dihydro-[1,2]oxazolo[4,5-c]pyridine-5-carboxylate 在 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 8.5h， 生成 3-(4-Bromophenyl)-5-prop-2-ynyl-6,7-dihydro-[1,2]oxazolo[4,5-c]pyridin-4-one
  参考文献：
  名称：

  Isoxazolodihydropyridinones: 1,3-Dipolar Cycloaddition of Nitrile Oxides onto 2,4-Dioxopiperidines

  摘要：

  Practical and efficient methods have been developed for the diversity-oriented synthesis of isoxazolodihydropyridinones via the 1,3-dipolar cycloaddition of nitrile oxides onto 2,4-dioxopiperidines. A select few of these isoxazolodihydropyridinones were further elaborated with triazoles by copper-catalyzed azide-alkyne cycloaddition reactions. A total of 70 compounds and intermediates were synthesized and analyzed for drug likeness. Sixty-four of these novel compounds were submitted to the NIH Molecular Libraries Small Molecule Repository for high-throughput biological screening.

  DOI：

  10.1021/co200200u

文献信息

• Isoxazolodihydropyridinones: 1,3-Dipolar Cycloaddition of Nitrile Oxides onto 2,4-Dioxopiperidines
  作者：Keith C. Coffman、Timothy P. Hartley、Jerry L. Dallas、Mark J. Kurth

  DOI：10.1021/co200200u

  日期：2012.4.9

  Practical and efficient methods have been developed for the diversity-oriented synthesis of isoxazolodihydropyridinones via the 1,3-dipolar cycloaddition of nitrile oxides onto 2,4-dioxopiperidines. A select few of these isoxazolodihydropyridinones were further elaborated with triazoles by copper-catalyzed azide-alkyne cycloaddition reactions. A total of 70 compounds and intermediates were synthesized and analyzed for drug likeness. Sixty-four of these novel compounds were submitted to the NIH Molecular Libraries Small Molecule Repository for high-throughput biological screening.