(5S)-5-isopropyl-5,6-dihydro-2H-1,4-oxazin-2-one | 175226-63-8

• 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-isopropyl-5,6-dihydro-2H-1,4-oxazin-2-one
• 英文别名: (5S)-5-isopropyl-5,6-dihydro-[1,4]oxazin-2-one；(3S)-3-propan-2-yl-2,3-dihydro-1,4-oxazin-6-one
• CAS: 175226-63-8
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: YVTZVXQOBFCVQQ-ZCFIWIBFSA-N

物化性质

• 沸点：
  190.2±23.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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-isopropyl-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， 以79%的产率得到(5S)-5-isopropyl-3,4,5,6-tetrahydro-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
• 作为产物：
  描述：

  L-缬氨醇 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 (5S)-5-isopropyl-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

• Highly diastereoselective synthesis of arylglycine derivatives via TFA-promoted Friedel–Crafts reactions of phenols with cyclic glyoxylate imines
  作者：Yong-Jun Chen、Fei Lei、Li Liu、Dong Wang

  DOI：10.1016/s0040-4020(03)01142-6

  日期：2003.9

  Optically active α-arylglycine derivatives were synthesized by Brønsted acid (TFA)-promoted Friedel–Crafts reaction of various phenols with chiral cyclic glyoxylate imines (2a–c), followed by deprotection with Pd(OH)2/C under H2. The diastereoselectivities of the initially formed F–C reaction products are up to 99%.

  通过布朗斯台德酸（TFA）促进的各种酚与手性环状乙醛酸亚胺（2a – c）的Friedel-Crafts反应，然后在H 2下用Pd（OH）2 / C脱保护，可以合成光学活性的α-芳基甘氨酸衍生物。最初形成的F–C反应产物的非对映选择性高达99％。
• 1,3-Stereoinduction in Radical Additions to Glyoxylate Imines
  作者：Michèle P. Bertrand、Laurence Feray、Robert Nouguier、Lucien Stella

  DOI：10.1055/s-1998-1763

  日期：1998.7

  Addition of alkyl radicals to the acyclic glyoxylate imine 1 proceeded with a 70 : 30 stereoinduction, even at -78 °C. Addition to the cyclic imine 4b resulted in complete stereocontrol at -40 °C.

  在-78°C下，烷基自由基对非环状乙二醛亚胺1的加成反应形成了70:30的立体诱导产物。而在-40°C时，对环状亚胺4b的加成则实现了完全的立体控制。
• 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。