(5R,6S)-4,5-dimethyl-6-phenylmorpholine-2,3-dione | 565204-52-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (5R,6S)-4,5-dimethyl-6-phenylmorpholine-2,3-dione
• CAS: 565204-52-6
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: APLZFAOVXIKLKF-PSASIEDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R,6S)-4,5-dimethyl-6-phenylmorpholine-2,3-dione 在 四氯化钛 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2S,5R,6S)-2-allyl-2-but-3-enyl-4,5-dimethyl-6-phenylmorpholin-3-one
  参考文献：
  名称：

  A Concise, Enantioselective Approach to (−)-Quinic Acid

  摘要：

  An expedient, enantioselective synthesis of a key precursor to (-)-quinic acid has been achieved from an ephedrine-derived morpholine-dione. The salient features of this approach are a highly diastereoselective conversion of the dione to a dialkenyl morpholinone and a subsequent ring-closing metathesis reaction. Removal of the ephedrine portion generates an enantiomerically enriched hydroxycyclohexene carboxamide that is readily converted to the quinic acid precursor.

  DOI：

  10.1021/ol060399h
• 作为产物：
  描述：

  草酰氯 、 盐酸右旋麻黄碱 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以55%的产率得到(5R,6S)-4,5-dimethyl-6-phenylmorpholine-2,3-dione
  参考文献：
  名称：

  A Concise, Enantioselective Approach to (−)-Quinic Acid

  摘要：

  An expedient, enantioselective synthesis of a key precursor to (-)-quinic acid has been achieved from an ephedrine-derived morpholine-dione. The salient features of this approach are a highly diastereoselective conversion of the dione to a dialkenyl morpholinone and a subsequent ring-closing metathesis reaction. Removal of the ephedrine portion generates an enantiomerically enriched hydroxycyclohexene carboxamide that is readily converted to the quinic acid precursor.

  DOI：

  10.1021/ol060399h

文献信息

• Reactivity of β-amino alcohols against dialkyl oxalate: synthesis and mechanism study in the formation of substituted oxalamide and/or morpholine-2,3-dione derivatives
  作者：Maria Luisa Testa、Elena Zaballos、Ramón J. Zaragozá

  DOI：10.1016/j.tet.2012.09.067

  日期：2012.11

  β-amino alcohols with dialkyl oxalates, in several reaction conditions, has been investigated. Linear disubstituted oxalamides were obtained with primary β-amino alcohols and linear tetrasubstituted oxalamides, or a mixture of linear tetrasubstituted oxalamides and cyclic morpholine-2,3-diones were obtained with N-substituted β-amino alcohols. A DFT study of the possible mechanism has been made. The theoretical

  在几种反应条件下，已经研究了各种β-氨基醇与草酸二烷基酯的反应性。用伯β-氨基醇和线性四取代的草酰胺获得线性二取代的草酰胺，或用N-取代的β-氨基醇获得线性的四取代草酰胺和环状吗啉-2，3-二酮的混合物。DFT研究了可能的机制。理论结果表明，这些反应不是动力学控制的，所有物质之间都存在平衡，因此遵循热力学控制。β-氨基伯醇与N的不同行为-甲基β-氨基醇是由于线性二取代的草酰胺相对于线性四取代的草酰胺具有更大的稳定性。四取代的草酰胺的能量更接近于相应的吗啉-2，3-二酮的能量。