t-butyl 3-(2-fluorophenyl)-4-oxo-6,7-dihydroisoxazolo[4,5-c]pyridine-5(4H)-carboxylate | 1246303-74-1

• 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: t-butyl 3-(2-fluorophenyl)-4-oxo-6,7-dihydroisoxazolo[4,5-c]pyridine-5(4H)-carboxylate
• 英文别名: Tert-butyl 3-(2-fluorophenyl)-4-oxo-6,7-dihydro-[1,2]oxazolo[4,5-c]pyridine-5-carboxylate
• CAS: 1246303-74-1
• 化学式: C₁₇H₁₇FN₂O₄
• 分子量: 332.331
• InChiKey: ATPHPRKKOBWXFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  72.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  t-butyl 3-(2-fluorophenyl)-4-oxo-6,7-dihydroisoxazolo[4,5-c]pyridine-5(4H)-carboxylate 在 copper(ll) sulfate pentahydrate 、 sodium hydride 、 sodium ascorbate 、 三氟乙酸 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 8.5h， 生成 3-(2-fluorophenyl)-5-((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)-6,7-dihydroisoxazolo[4,5-c]pyridin-4(5H)-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：

  Boc-beta-丙氨酸 在 4-二甲氨基吡啶 、 sodium hydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 t-butyl 3-(2-fluorophenyl)-4-oxo-6,7-dihydroisoxazolo[4,5-c]pyridine-5(4H)-carboxylate
  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

• Orthogonally Protected Thiazole and Isoxazole Diamino Acids: An Efficient Synthetic Route
  作者：Jeffrey D. Butler、Keith C. Coffman、Kristin T. Ziebart、Michael D. Toney、Mark J. Kurth

  DOI：10.1002/chem.201001492

  日期：——

  An efficient strategy has been developed for the synthesis of heteroaromatic amino acids (HAAs). These methods generate mono‐ or orthogonally protected diamino acids from β‐amino acids (see scheme). Their synthetic reliability and biological potential was demonstrated through the synthesis of an anthranilate synthase (AS) and isochorismate synthase (IS) inhibitor with improved potency.

  已开发出一种用于合成杂芳族氨基酸 (HAA)的有效策略。这些方法从 β-氨基酸生成单或正交保护的二氨基酸（见方案）。通过合成具有改进效力的邻氨基苯甲酸合酶 (AS) 和异分支酸合酶 (IS) 抑制剂，证明了它们的合成可靠性和生物学潜力。
• 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.