(3R,6R)-6-isopropyl-2-phenyl-3-propyl-3,6-dihydro-2H-1,2-oxazine-4-carbaldehyde | 1388837-36-2

• 分子结构分类: 有机化合物 - 苯类化合物 - N-苯基羟胺
• 英文名称: (3R,6R)-6-isopropyl-2-phenyl-3-propyl-3,6-dihydro-2H-1,2-oxazine-4-carbaldehyde
• 英文别名: (3R,6R)-2-phenyl-6-propan-2-yl-3-propyl-3,6-dihydrooxazine-4-carbaldehyde
• CAS: 1388837-36-2
• 化学式: C₁₇H₂₃NO₂
• 分子量: 273.375
• InChiKey: CHEYRVHRGMNFKP-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-已烯醛 、 亚硝基苯 、 异戊醛 在 L-脯氨酸 、 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 25.0h， 以58%的产率得到(3R,6R)-6-isopropyl-2-phenyl-3-propyl-3,6-dihydro-2H-1,2-oxazine-4-carbaldehyde
  参考文献：
  名称：

  Highly Efficient Asymmetric Synthesis of Enantiopure Dihydro-1,2-oxazines: Dual-Organocatalyst-Promoted Asymmetric Cascade Reaction

  摘要：

  A one-pot dual-organocatalyst-promoted asymmetric alpha-aminoxylation/aza-Michael/aldol consendation cascade reaction is presented. The targeted optically active 1,2-oxazine derivatives are synthesized in moderate yields (up to 70%), excellent enantioselectivities (ee >99% in all cases), and excellent diastereoselectivities (dr up to >99:1) under mild conditions. To further elucidate the synthetic utility of the cascade products, cleavage of the N-O bond is demonstrated and an enantiopure syn-1,4-amino alcohol derivative is achieved in excellent yield.

  DOI：

  10.1021/ol301218x

文献信息

• Highly Efficient Asymmetric Synthesis of Enantiopure Dihydro-1,2-oxazines: Dual-Organocatalyst-Promoted Asymmetric Cascade Reaction
  作者：Hua Lin、Yu Tan、Xing-Wen Sun、Guo-Qiang Lin

  DOI：10.1021/ol301218x

  日期：2012.8.3

  A one-pot dual-organocatalyst-promoted asymmetric alpha-aminoxylation/aza-Michael/aldol consendation cascade reaction is presented. The targeted optically active 1,2-oxazine derivatives are synthesized in moderate yields (up to 70%), excellent enantioselectivities (ee >99% in all cases), and excellent diastereoselectivities (dr up to >99:1) under mild conditions. To further elucidate the synthetic utility of the cascade products, cleavage of the N-O bond is demonstrated and an enantiopure syn-1,4-amino alcohol derivative is achieved in excellent yield.