(5S)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one | 175226-64-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪类
• 英文名称: (5S)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one
• 英文别名: (5R)-5-Phenyl-5,6-dihydro-2H-1,4-oxazin-2-one；(3R)-3-phenyl-2,3-dihydro-1,4-oxazin-6-one
• CAS: 175226-64-9
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: DINGSFSTMYUIAU-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 生成 (5R)-3,4,5,6-四氢-5-苯基-4(H)-1,4-恶嗪-2-酮
  参考文献：
  名称：

  Oxidative Rearrangement of 2-Substituted Oxazolines. A Novel Entry to 5,6-Dihydro-2H-1,4-oxazin-2-ones and Morpholin-2-ones

  摘要：

  A novel synthesis of 5,6-dihydro-2H-1,4-oxazin-2-ones by SeO2-promoted oxidative rearrangement of 2-alkyl- and 2-(arylmethyl)oxazolines is described. Yields are good to excellent; (up to 94%) with the highest yields obtained for 2-arylmethyl- and 2-neopentyl-substituted oxazolines. This reaction provides convenient access to novel 5-aryl-substituted dihydrooxazinones in high yield. The latter compounds are important ''chiral glycine'' synthons for asymmetric synthesis of a-amino acids. Since oxazolines are readily derived from carboxylic acids or their equivalents, this oxidative rearrangement constitutes an entry to synthesis of a-amino acids from carboxylic acids. A mechanism is proposed to account for the rearrangement involving a ''nitrilium to acylium'' 1,2-migration.

  DOI：

  10.1021/jo952144f
• 作为产物：
  描述：

  (R)-2-methyl-4-phenyl-Δ²-oxazoline 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以72%的产率得到(5S)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one
  参考文献：
  名称：

  Oxidative Rearrangement of 2-Substituted Oxazolines. A Novel Entry to 5,6-Dihydro-2H-1,4-oxazin-2-ones and Morpholin-2-ones

  摘要：

  A novel synthesis of 5,6-dihydro-2H-1,4-oxazin-2-ones by SeO2-promoted oxidative rearrangement of 2-alkyl- and 2-(arylmethyl)oxazolines is described. Yields are good to excellent; (up to 94%) with the highest yields obtained for 2-arylmethyl- and 2-neopentyl-substituted oxazolines. This reaction provides convenient access to novel 5-aryl-substituted dihydrooxazinones in high yield. The latter compounds are important ''chiral glycine'' synthons for asymmetric synthesis of a-amino acids. Since oxazolines are readily derived from carboxylic acids or their equivalents, this oxidative rearrangement constitutes an entry to synthesis of a-amino acids from carboxylic acids. A mechanism is proposed to account for the rearrangement involving a ''nitrilium to acylium'' 1,2-migration.

  DOI：

  10.1021/jo952144f

文献信息

• Allyl Silane Additions to Highly Electrophilic 5,6-Dihydro-2H-1,4- oxazinones
  作者：Cynthia Shafer、Julie Pigza、Tadeusz Molinski

  DOI：10.2174/157017809787893046

  日期：2009.4.1

  Allylsilane addition to the dihydro-2H-1,4-oxazinones, 1, proceeded in moderate to good yields with transdiastereoselectivity. The yield of addition reactions of 5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one with allylsilanes is improved over the corresponding additions of Grignard reagents to 1 and illustrates a simple path to protected β,β- disubstituted α-amino acids.

  烯丙基硅烷对二氢-2H-1,4-恶嗪酮 1 的加成反应具有中等至良好的产率和反式对映选择性。5-苯基-5,6-二氢-2H-1,4-恶嗪-2-酮与烯丙基硅烷的加成反应的收率比格氏试剂与 1 的相应加成反应的收率要高，说明了一种获得受保护的 β、β- 二取代 α-氨基酸的简单途径。
• Highly Diastereoselective Synthesisof 3-Indolyl-<i>N</i>-Substituted Glycine Derivativesvia TFA-Promoted Friedel-Crafts Type Reaction of Indoleswith Chiral Cyclic Glyoxylate Imine
  作者：Yong-Jun Chen、Dong Wang、Fei Lei、Yong Sui、Li Liu

  DOI：10.1055/s-2003-39905

  日期：——

  A method based on the highly diastereoselective Friedel-Crafts type reaction of indoles with chiral cyclic glyoxylate imines in the presence of TFA toward the stereoselective synthesis of 3-indolyl-N-substituted glycine derivatives is presented. The absolute configuration of the newly formed chiral center was determined by a single-crystal X-ray analysis.

  本文介绍了一种基于高度立体选择性Friedel-Crafts反应的方法，该反应在TFA存在下，将吲哚与手性环状乙醛酸亚胺反应，从而实现3-吲哚基-N-取代甘氨酸衍生物的立体选择性合成。新形成的手性中心的绝对构型通过单晶X射线分析确定。
• Oxidative Rearrangement of 2-Substituted Oxazolines. A Novel Entry to 5,6-Dihydro-2<i>H</i>-1,4-oxazin-2-ones and Morpholin-2-ones
  作者：Cynthia M. Shafer、Tadeusz F. Molinski

  DOI：10.1021/jo952144f

  日期：1996.1.1

  A novel synthesis of 5,6-dihydro-2H-1,4-oxazin-2-ones by SeO2-promoted oxidative rearrangement of 2-alkyl- and 2-(arylmethyl)oxazolines is described. Yields are good to excellent; (up to 94%) with the highest yields obtained for 2-arylmethyl- and 2-neopentyl-substituted oxazolines. This reaction provides convenient access to novel 5-aryl-substituted dihydrooxazinones in high yield. The latter compounds are important ''chiral glycine'' synthons for asymmetric synthesis of a-amino acids. Since oxazolines are readily derived from carboxylic acids or their equivalents, this oxidative rearrangement constitutes an entry to synthesis of a-amino acids from carboxylic acids. A mechanism is proposed to account for the rearrangement involving a ''nitrilium to acylium'' 1,2-migration.