(RS)-1-benzoyl-2-methyl-2,3-dihydro-1H-pyridin-4-one | 214626-85-4

• 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: (RS)-1-benzoyl-2-methyl-2,3-dihydro-1H-pyridin-4-one
• 英文别名: 1-Benzoyl-2-methyl-2,3-dihydropyridin-4(1H)-one；1-benzoyl-2-methyl-2,3-dihydropyridin-4-one
• CAS: 214626-85-4
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: CLPLVBNNTSXDPM-UHFFFAOYSA-N

物化性质

• 熔点：
  126-127 °C
• 沸点：
  365.4±35.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (RS)-1-benzoyl-2-methyl-2,3-dihydro-1H-pyridin-4-one 在 sodium methylate 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.5h， 生成 1,2-二甲基-2,3-二氢-4(1H)-吡啶酮
  参考文献：
  名称：

  Synthesis of β-Amino Acids Based on Oxidative Cleavage of Dihydropyridone Derivatives

  摘要：

  A new method for the synthesis of beta-amino acids based on 2,3-dihydropyridones as starting materials is presented. Conversions of 2,3-dihydropyridones with NalO(4) and subsequently with base gave the corresponding beta-amino acids in a one-pot procedure. The reactions have been monitored by H-1 NMR indicating that the beta-amino acids were formed in quantitative yields mostly. This method appears to be of broad scope, as 2-substituted 2,3-dihydropyridones are easily accessible via N-acyliminium ions generated from 4-methoxypyridine.

  DOI：

  10.1021/ol0485518
• 作为产物：
  描述：

  4-甲氧基吡啶 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (RS)-1-benzoyl-2-methyl-2,3-dihydro-1H-pyridin-4-one
  参考文献：
  名称：

  Synthesis of β-Amino Acids Based on Oxidative Cleavage of Dihydropyridone Derivatives

  摘要：

  A new method for the synthesis of beta-amino acids based on 2,3-dihydropyridones as starting materials is presented. Conversions of 2,3-dihydropyridones with NalO(4) and subsequently with base gave the corresponding beta-amino acids in a one-pot procedure. The reactions have been monitored by H-1 NMR indicating that the beta-amino acids were formed in quantitative yields mostly. This method appears to be of broad scope, as 2-substituted 2,3-dihydropyridones are easily accessible via N-acyliminium ions generated from 4-methoxypyridine.

  DOI：

  10.1021/ol0485518

文献信息

• Diastereoselective synthesis of β-amino acid derivatives from dihydropyridones
  作者：Markus Ege、Klaus T. Wanner

  DOI：10.1016/j.tet.2008.05.073

  日期：2008.7

  A new method for the diastereoselective preparation of stereoisomeric 2,3-disubstituted β-amino acids is presented. It is based on trans- and cis-2,3-disubstituted dihydropyridones, which were derived from 2-monosubstituted N-acyl dihydropyridone derivatives. Alkylation of the enolates of 2-substituted dihydropyridones gave trans-2,3-disubstituted dihydropyridones with high diastereoselectivities.

  提出了一种非对映选择性制备立体异构体2,3-二取代的β-氨基酸的新方法。它是基于反式-和顺-2,3-二取代的二氢吡啶，将其衍生自2单取代Ñ酰基二氢吡啶酮衍生物。2-取代的二氢吡啶酮的烯醇盐的烷基化得到具有高非对映选择性的反式-2,3-二取代的二氢吡啶酮。通过去质子化/再质子化序列使二氢吡啶酮核的C-3处的立体中心反转，从而以高收率和非对映选择性产生了立体异构体顺式-2,3-二取代的二氢吡啶酮。除去N之后-酰基保护基团，高碘酸钠分别氧化生成的顺式或反式-2,3-异位二氢吡啶酮，导致相应的非对映体β-氨基酸氧化降解。
• Solid phase synthesis of N-acyl-2-substituted-dihydro-4-pyridone: Resin Activation/Capture Approach/REACAP Technology
  作者：Chixu Chen、Benito Munoz

  DOI：10.1016/s0040-4039(98)01489-0

  日期：1998.9

  Resin Activation/Capture (REACAP) Technology was used to prepare N-acyl-2-substituted-dihydro-4-pyridone analogs.

  树脂活化/捕获（REACAP）技术用于制备N-酰基-2-取代的二氢-4-吡啶酮类似物。
• Synthesis of β-Amino Acids Based on Oxidative Cleavage of Dihydropyridone Derivatives
  作者：Markus Ege、Klaus T. Wanner

  DOI：10.1021/ol0485518

  日期：2004.9.1

  A new method for the synthesis of beta-amino acids based on 2,3-dihydropyridones as starting materials is presented. Conversions of 2,3-dihydropyridones with NalO(4) and subsequently with base gave the corresponding beta-amino acids in a one-pot procedure. The reactions have been monitored by H-1 NMR indicating that the beta-amino acids were formed in quantitative yields mostly. This method appears to be of broad scope, as 2-substituted 2,3-dihydropyridones are easily accessible via N-acyliminium ions generated from 4-methoxypyridine.