(4R,5S,6R)-4,5-Dimethyl-6-phenyl-3-(3-phenyl-propionyl)-[1,3,4]oxadiazinan-2-one | 660849-11-6

• 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: (4R,5S,6R)-4,5-Dimethyl-6-phenyl-3-(3-phenyl-propionyl)-[1,3,4]oxadiazinan-2-one
• CAS: 660849-11-6
• 化学式: C₂₀H₂₂N₂O₃
• 分子量: 338.406
• InChiKey: CDISEUOPMOVHPI-KXBFYZLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.85
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-萘甲醛 、 (4R,5S,6R)-4,5-Dimethyl-6-phenyl-3-(3-phenyl-propionyl)-[1,3,4]oxadiazinan-2-one 在 四氯化钛 、 三乙胺 作用下， 生成 (4R,5S,6R)-3-(2-Benzyl-3-hydroxy-3-naphthalen-2-yl-propionyl)-4,5-dimethyl-6-phenyl-[1,3,4]oxadiazinan-2-one 、 (4R,5S,6R)-3-((2S,3S)-2-Benzyl-3-hydroxy-3-naphthalen-2-yl-propionyl)-4,5-dimethyl-6-phenyl-[1,3,4]oxadiazinan-2-one
  参考文献：
  名称：

  Toward the Development of a Structurally Novel Class of Chiral Auxiliaries. Conformational Properties of the Aldol Adducts of Oxadiazinones:  Observation of Unusual Shielding Effects

  摘要：

  Asymmetric aldol reactions were conducted with the titanium enolate of N-3-hydrocinnamoyl-3,4,5,6tetrahydro-2H-1,3,4-oxadiazin-2-one to afford aldol adducts 5a-j. The dominant product of the asymmetric aldol reaction was the non-Evans syn adduct as determined by N-1 NMR spectroscopy and X-ray crystallography. When evaluating the N-1 NMR spectra of adducts 5a-j, a highly shielded signal with an average chemical shift of 0.05 ppm was observed. This signal was readily determined to be the C-5-methyl group of the oxadiazinone. It is presumed that the overall conformation adopted by the aldol adducts in solution places an aromatic ring of the N-3-substituent in close proximity to the C-5-methyl group. An investigation of this conformational preference is conducted employing H-1 NMR spectroscopy, X-ray crystallography, and computational methods.

  DOI：

  10.1021/jo035481u
• 作为产物：
  描述：

  (5S,6R)-4,5-dimethyl-6-phenyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one 、 3-苯丙酰氯 在 lithium hydride 作用下， 以 二氯甲烷 为溶剂， 生成 (4R,5S,6R)-4,5-Dimethyl-6-phenyl-3-(3-phenyl-propionyl)-[1,3,4]oxadiazinan-2-one
  参考文献：
  名称：

  Toward the Development of a Structurally Novel Class of Chiral Auxiliaries. Conformational Properties of the Aldol Adducts of Oxadiazinones:  Observation of Unusual Shielding Effects

  摘要：

  Asymmetric aldol reactions were conducted with the titanium enolate of N-3-hydrocinnamoyl-3,4,5,6tetrahydro-2H-1,3,4-oxadiazin-2-one to afford aldol adducts 5a-j. The dominant product of the asymmetric aldol reaction was the non-Evans syn adduct as determined by N-1 NMR spectroscopy and X-ray crystallography. When evaluating the N-1 NMR spectra of adducts 5a-j, a highly shielded signal with an average chemical shift of 0.05 ppm was observed. This signal was readily determined to be the C-5-methyl group of the oxadiazinone. It is presumed that the overall conformation adopted by the aldol adducts in solution places an aromatic ring of the N-3-substituent in close proximity to the C-5-methyl group. An investigation of this conformational preference is conducted employing H-1 NMR spectroscopy, X-ray crystallography, and computational methods.

  DOI：

  10.1021/jo035481u