(2S,5R,6S)-6-methyl-5-[(4S)-2-oxo-4-phenyloxazolidin-3-yl]-2-phenyl-1,3-oxazinan-4-one | 350045-25-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,5R,6S)-6-methyl-5-[(4S)-2-oxo-4-phenyloxazolidin-3-yl]-2-phenyl-1,3-oxazinan-4-one
• 英文别名: (2S,5R,6S)-6-methyl-5-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]-2-phenyl-1,3-oxazinan-4-one
• CAS: 350045-25-9
• 化学式: C₂₀H₂₀N₂O₄
• 分子量: 352.39
• InChiKey: ZLEMPRUTUSAEQF-YUFWVBKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,5R,6S)-6-methyl-5-[(4S)-2-oxo-4-phenyloxazolidin-3-yl]-2-phenyl-1,3-oxazinan-4-one 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 (2R,3R)-2-[(4S)-2-oxo-4-phenyloxazolidin-3-yl]-3-hydroxybutanoic acid
  参考文献：
  名称：

  Synthesis of perhydroxazin-4-ones. Competitive Mukaiyama versus hetero Diels–Alder reaction in the cycloaddition of 2-aza-3-trimethylsilyloxy-1,3-butadiene and aldehydes

  摘要：

  The reactions of 2-aza-3-trimethylsilyloxy-1,3-butadiene with carbonyl dienophiles are described. 2-Aza-1,3-butadienes participate as dienes in the [4+2] cycloaddition with aldehydes to afford perhydroxazin-4-ones in good yields. Experimental results, however, show that a Mukaiyama type two-step reaction must be taken into account. The cycloadducts obtained have proved to be useful intermediates in the synthesis of alpha -amino-beta -hydroxy acids. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00051-9
• 作为产物：
  描述：

  2-(4(S)-phenyloxazolidin-2-on-3-yl)acetyl chloride 在 三氟化硼乙醚 、 三乙胺 作用下， 以 正庚烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 (2S,5R,6S)-6-methyl-5-[(4S)-2-oxo-4-phenyloxazolidin-3-yl]-2-phenyl-1,3-oxazinan-4-one
  参考文献：
  名称：

  Synthesis of perhydroxazin-4-ones. Competitive Mukaiyama versus hetero Diels–Alder reaction in the cycloaddition of 2-aza-3-trimethylsilyloxy-1,3-butadiene and aldehydes

  摘要：

  The reactions of 2-aza-3-trimethylsilyloxy-1,3-butadiene with carbonyl dienophiles are described. 2-Aza-1,3-butadienes participate as dienes in the [4+2] cycloaddition with aldehydes to afford perhydroxazin-4-ones in good yields. Experimental results, however, show that a Mukaiyama type two-step reaction must be taken into account. The cycloadducts obtained have proved to be useful intermediates in the synthesis of alpha -amino-beta -hydroxy acids. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00051-9

文献信息

• Synthesis of perhydroxazin-4-ones. Competitive Mukaiyama versus hetero Diels–Alder reaction in the cycloaddition of 2-aza-3-trimethylsilyloxy-1,3-butadiene and aldehydes
  作者：Alessandro Bongini、Mauro Panunzio、Elisa Bandini、Eileen Campana、Giorgio Martelli、Giuseppe Spunta

  DOI：10.1016/s0957-4166(01)00051-9

  日期：2001.3

  The reactions of 2-aza-3-trimethylsilyloxy-1,3-butadiene with carbonyl dienophiles are described. 2-Aza-1,3-butadienes participate as dienes in the [4+2] cycloaddition with aldehydes to afford perhydroxazin-4-ones in good yields. Experimental results, however, show that a Mukaiyama type two-step reaction must be taken into account. The cycloadducts obtained have proved to be useful intermediates in the synthesis of alpha -amino-beta -hydroxy acids. (C) 2001 Elsevier Science Ltd. All rights reserved.