N-(3,4-二氢-2H-吡喃-5-基)苯甲酰胺 | 887236-68-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(3,4-二氢-2H-吡喃-5-基)苯甲酰胺
• 英文名称: Benzamide, N-(3,4-dihydro-2H-pyran-5-yl)-
• 英文别名: N-(3,4-dihydro-2H-pyran-5-yl)benzamide
• CAS: 887236-68-2
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: GUPAZGINNPCEOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3,4-二氢-2H-吡喃-5-基)苯甲酰胺 在 二(三苯基膦)环戊二烯基氯化钌(II) 2-双环己基膦-2',6'-二甲氧基联苯 、 2-氯吡啶 、 ammonium hexafluorophosphate 、 trifluoromethanesulfonic acid anhydride 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 6-phenyl-3,4-dihydro-2H-pyrano[3,2-b]pyridine
  参考文献：
  名称：

  Synthesis of Substituted Pyridines and Quinolines

  摘要：

  各种 N-乙烯基和 N-芳基酰胺分别被转化为相应的吡啶和喹啉衍生物。酰胺活化和亲核加成铜(I) (三甲基硅烷基)乙酰化物能有效地提供所需的炔亚胺。在钌催化下，这些亚胺发生原代甲硅烷基化和环异构化反应，生成相应的杂杂环。

  DOI：

  10.1055/s-2007-965940

文献信息

• Direct Synthesis of Substituted Pyrimidines and Quinazolines
  作者：Mohammad Movassaghi、Matthew Hill

  DOI：10.1055/s-2007-990932

  日期：2008.3

  A variety of N-vinyl and N-aryl amides were converted in one step into the corresponding pyrimidine and quinazoline derivatives, respectively. Amide activation with trifluoromethanesulfonic anhydride in the presence of 2-chloropyridine followed by nitrile addition to the activated amide derivative and annulation provides the desired azaheterocycles.

  各种 N-乙烯基和 N-芳基酰胺在一个步骤中分别转化为相应的嘧啶和喹唑啉衍生物。在 2-氯吡啶存在下，先用三氟甲磺酸酐进行酰胺活化，然后将腈加到活化的酰胺衍生物中并环化，就得到了所需的杂杂环。
• New Strategies for the Synthesis of Pyrimidine Derivatives
  作者：Matthew D. Hill、Mohammad Movassaghi

  DOI：10.1002/chem.200800014

  日期：2008.8.8

  Recent advances in pyrimidine synthesis are described. Modification of conventional strategies involving N-C-N fragment condensation with 1,3-dicarbonyl derivatives remains a common theme in current literature. Other methods, including N-C fragment condensation strategies, provide reactive intermediates capable of intramolecular cyclization and formation of pyrimidine derivatives. These recently developed

  描述了嘧啶合成的最新进展。涉及NCN片段与1，3-二羰基衍生物缩合的常规策略的修改仍然是当前文献中的共同主题。其他方法，包括NC片段缩合策略，提供了能够分子内环化和形成嘧啶衍生物的反应性中间体。这些最近开发的方法为氮杂杂环合成提供了宝贵的补充。
• Synthesis of Substituted Pyridine Derivatives via the Ruthenium-Catalyzed Cycloisomerization of 3-Azadienynes
  作者：Mohammad Movassaghi、Matthew D. Hill

  DOI：10.1021/ja060626a

  日期：2006.4.1

  respectively. The process involves the direct conversion of amides, including sensitive N-vinyl amides, to the corresponding trimethylsilyl alkynyl imines followed by a ruthenium-catalyzed protodesilylation and cycloisomerization. A wide range of new alkynyl imines are prepared and readily converted to the corresponding azaheterocycles.

  我们描述了各种 N-乙烯基和 N-芳基酰胺分别向相应的取代吡啶和喹啉的两步转化。该过程涉及将酰胺（包括敏感的 N-乙烯基酰胺）直接转化为相应的三甲基甲硅烷基炔基亚胺，然后是钌催化的原脱甲硅烷化和环异构化。广泛的新炔基亚胺被制备并容易转化为相应的氮杂杂环。
• Direct Synthesis of Pyridine Derivatives
  作者：Mohammad Movassaghi、Matthew D. Hill、Omar K. Ahmad

  DOI：10.1021/ja073912a

  日期：2007.8.1

  We describe a single-step conversion of various N-vinyl and N-aryl amides to the corresponding pyridine and quinoline derivatives, respectively. The process involves amide activation with trifluoromethanesulfonic anhydride in the presence of 2-chloropyridine followed by pi-nucleophile addition to the activated intermediate and annulation. Compatibility of this chemistry with sensitive N-vinyl amides, epimerizable substrates, and a variety of functional groups is noteworthy.
• Single-Step Synthesis of Pyrimidine Derivatives
  作者：Mohammad Movassaghi、Matthew D. Hill

  DOI：10.1021/ja066405m

  日期：2006.11.1

  We describe a single-step conversion of various N-vinyl and N-aryl amides to the corresponding pyrimidine and quinazoline derivatives, respectively. The process involves amide activation with 2-chloropyridine and trifluoromethanesulfonic anhydride followed by nitrile addition into the reactive intermediate and cycloisomerization. In situ nitrile generation from primary amides allows for their use as nitrile surrogates. The use of this chemistry with sensitive N-vinyl amides and epimerizable substrates in addition to a wide range of functional groups is noteworthy.