tert-butyl (3-oxo-5-phenylpent-4-yn-1-yl)carbamate | 1321589-04-1

• 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: tert-butyl (3-oxo-5-phenylpent-4-yn-1-yl)carbamate
• 英文别名: tert-butyl 3-oxo-5-phenylpent-4-ynylcarbamate；tert-butyl N-(3-oxo-5-phenylpent-4-ynyl)carbamate
• CAS: 1321589-04-1
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: LUUXQJHKIDHOFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (3-oxo-5-phenylpent-4-yn-1-yl)carbamate 在 N-溴代丁二酰亚胺(NBS) 、 silver hexafluoroantimonate 、 三苯基膦氯金 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.08h， 以91%的产率得到Tert-butyl 5-bromo-4-oxo-6-phenyl-2,3-dihydropyridine-1-carboxylate
  参考文献：
  名称：

  Gold-Mediated Synthesis and Functionalization of Chiral Halopyridones

  摘要：

  A rapid and efficient one-step halopyridone synthesis has been developed based on gold-catalyzed cyclization of beta-amino-ynone intermediates and halodeauration process.

  DOI：

  10.1021/jo400827b
• 作为产物：
  描述：

  Diazo-(N-tert-butoxycarbonylglycyl)methane 在 正丁基锂 、 silver nitrate 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.5h， 生成 tert-butyl (3-oxo-5-phenylpent-4-yn-1-yl)carbamate
  参考文献：
  名称：

  Enantiospecific Synthesis of Pyridinones as Versatile Intermediates toward Asymmetric Piperidines

  摘要：

  The enantiospecific syntheses of pyridinones from amino acids via a gold-catalyzed strategy are reported. Excellent stereocontrol was observed during the cyclization. This approach provides a straightforward tool for further synthetic applications toward piperidines.

  DOI：

  10.1021/ol201698m

文献信息

• Accessing spiropiperidines from dihydropyridones through tandem triflation–allylation and ring-closing metathesis (RCM)
  作者：Naresh Gantasala、Corentin Fournet、Myriam Le Roch、Claudia Lalli、Srihari Pabbaraja、Nicolas Gouault

  DOI：10.1039/d3ob00545c

  日期：——

  allyltributylstannane onto dihydropyridones allowed for the formation of gem bis-alkenyl intermediates that were converted to the corresponding spirocarbocycles with excellent yields via ring closing metathesis. The vinyl triflate group generated on these 2-spiro-dihydropyridine intermediates could be successfully used as a chemical expansion vector for further transformations namely Pd-catalyzed cross-coupling

  开发了一种从二氢吡啶酮开始构建 2-螺哌啶部分的新方法。三氟甲磺酸酐促进烯丙基三丁基锡烷在二氢吡啶酮上的共轭加成允许形成偕双烯基中间体，该中间体通过闭环复分解以优异的产率转化为相应的螺碳环。这些 2-螺二氢吡啶中间体上生成的三氟甲磺酸乙烯酯基团可以成功地用作进一步转化（即 Pd 催化的交叉偶联反应）的化学膨胀载体。
• Synthesis and Chemoinformatic Analysis of Fluorinated Piperidines as 3D Fragments for Fragment-Based Drug Discovery
  作者：Myriam Le Roch、Jacques Renault、Gilles Argouarch、Elena Lenci、Andrea Trabocchi、Thierry Roisnel、Nicolas Gouault、Claudia Lalli

  DOI：10.1021/acs.joc.4c00143

  日期：2024.4.5

  then been evaluated by chemoinformatic tools. In particular, the compounds' pKa's have been calculated, revealing that the fluorine atoms notably lowered their basicity, which is correlated to the affinity for hERG channels resulting in cardiac toxicity. The “lead-likeness” and three-dimensionality have also been evaluated to assess their ability as useful fragments for drug design. A random screening

  已经描述了从容易获得的二氢吡啶酮衍生物中简明合成小型氟化哌啶库。然后通过化学信息学工具评估氟化对不同位置的影响。特别是，计算了化合物的pKa值，表明氟原子显着降低了它们的碱性，这与导致心脏毒性的 hERG 通道的亲和力相关。还对“先导相似性”和三维度进行了评估，以评估它们作为药物设计有用片段的能力。然后对一组代表性蛋白水解酶进行随机筛选，结果发现一个支架被 3CL Pro （SARS-CoV-2 冠状病毒的主要蛋白酶）的催化口袋识别。
• Enantiospecific Synthesis of Pyridinones as Versatile Intermediates toward Asymmetric Piperidines
  作者：Nicolas Gouault、Myriam Le Roch、Adèle Cheignon、Philippe Uriac、Michèle David

  DOI：10.1021/ol201698m

  日期：2011.8.19

  The enantiospecific syntheses of pyridinones from amino acids via a gold-catalyzed strategy are reported. Excellent stereocontrol was observed during the cyclization. This approach provides a straightforward tool for further synthetic applications toward piperidines.
• Gold-Mediated Synthesis and Functionalization of Chiral Halopyridones
  作者：Khanh Hung Nguyen、Sophie Tomasi、Myriam Le Roch、Loïc Toupet、Jacques Renault、Philippe Uriac、Nicolas Gouault

  DOI：10.1021/jo400827b

  日期：2013.8.16

  A rapid and efficient one-step halopyridone synthesis has been developed based on gold-catalyzed cyclization of beta-amino-ynone intermediates and halodeauration process.