(S)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one | 183023-15-6

• 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: (S)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one
• 英文别名: (S)-5,6-dihydro-2H-5-phenyl-1,4-oxazin-2-one；2H-1,4-Oxazin-2-one, 5,6-dihydro-5-phenyl-, (5S)-；(3S)-3-phenyl-2,3-dihydro-1,4-oxazin-6-one
• CAS: 183023-15-6
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: DINGSFSTMYUIAU-SECBINFHSA-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：

  (S)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 三氟化硼乙醚 作用下， 生成 (3S,5S)-3-benzyl-5-phenyl-3,4,5,6-tetrahydro-1,4-oxazin-2-one
  参考文献：
  名称：

  Synthesis of enantiomerically pure α-amino acids via chemo- and diastereoselective alkylation of (5S)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one

  摘要：

  (5S)-5-苯基-5,6-二氢-2H-1,4-氧嗪-2-酮在路易斯酸介导下进行化学和立体选择性良好的Grignard试剂亲核加成反应，生成加成物。随后，该加成物可以通过简便的方法转化为光学纯的(S)-α-氨基酸。版权(C) 1997 Elsevier Science Ltd. 所有权利保留。

  DOI：

  10.1016/s0957-4166(97)00587-9
• 作为产物：
  描述：

  (5S)-3,4,5,6-四氢-5-苯基-4(H)-1,4-恶嗪-2-酮 在 N-溴代丁二酰亚胺(NBS) 、 methyloxirane 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以55%的产率得到(S)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one
  参考文献：
  名称：

  Synthesis, isomerisation and diels-alder reactions of (5S)-5-phenyl-3,4-dehydromorpholin-2-one

  摘要：

  (5S)-5-苯基-3,4-去氢吗啉-2-酮[(5S)-5-苯基-5,6-二氢-2H-1,4-氧嗪-2-酮]2a 是通过一锅法溴化/脱氢溴化反应从(SS)-5-苯基吗啉-2-酮制备，并在具有区域和对映选择性的催化的Diels-Alder反应中发生反应。版权(C)1996 Elsevier Science Ltd。

  DOI：

  10.1016/0957-4166(96)00329-1

文献信息

• An Asymmetric Ugi Three-Component Reaction Induced by Chiral Cyclic Imines: Synthesis of Morpholin– or Piperazine–Keto-carboxamide Derivatives
  作者：Deguang Zhu、Liang Xia、Li Pan、Sheng Li、Ruijiao Chen、Yongren Mou、Xiaochuan Chen

  DOI：10.1021/jo2021967

  日期：2012.2.3

  4-oxazin-2-one substrates, as preformed cyclic aldimines and ketoimines, were employed to develop a new asymmetric Ugi three-component reaction for the first time. The Ugi reaction of the imines, isocyanides, and carboxylic acids opens an efficient access to novel morpholin-2-one-3-carboxamide compounds. The chiral imines showed promising stereoinduction for the new chiral center of the Ugi products, and

  一系列手性5,6-二氢-1,4-恶嗪-2-酮底物，如预先形成的环状醛亚胺和酮亚胺，首次用于开发新的不对称Ugi三组分反应。亚胺，异氰酸酯和羧酸的Ugi反应使人们可以有效地获得新型的吗啉-2-二-3-甲酰胺化合物。手性亚胺对Ugi产品的新手性中心显示出有希望的立体诱导，并且在大多数情况下获得了主要的反式异构体。添加一些路易斯酸或质子酸可以进一步提高非对映选择性，但通常会导致总收率下降。Ugi-3CR可以扩展到ketopiperazine-2-carboxamide衍生物的立体选择性合成。
• An Efficient Procedure for the Synthesis of Morpholin-2-one-3-carboxamide Derivatives in Good Diastereoselectivity by the Ugi Reaction
  作者：Xiaochuan Chen、Deguang Zhu、Ruijiao Chen、Haibo Liang、Sheng Li、Li Pan

  DOI：10.1055/s-0029-1219533

  日期：2010.4

  series of 5-substituted morpholin-2-one-3-carbox-amide derivatives were efficiently synthesized by a Ugi three-component reaction involving chiral 5,6-dihydro[1,4]oxazin-2-one substrates, isocyanides and carboxylic acids. The newly formed chiral center in the product was obtained in good diastereoselectivity.

  通过涉及手性 5,6-二氢[1,4]恶嗪-2-one 底物、异氰化物和羧酸的 Ugi 三组分反应有效合成了一系列 5-取代吗啉-2-one-3-羧酰胺衍生物酸。产物中新形成的手性中心以良好的非对映选择性获得。
• 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。
• Total Synthesis of Polydiscamides B, C, and D via a Convergent Native Chemical Ligation–Oxidation Strategy
  作者：Gajan Santhakumar、Richard J. Payne

  DOI：10.1021/ol502045u

  日期：2014.9.5

  The first total syntheses of the marine sponge-derived cyclic depsipeptide natural products Polydiscamides B, C, and D are described. The molecules were constructed through the convergent fusion of cyclic and linear fragments via an unprecedented native chemical ligation–oxidation protocol.

  描述了海洋海绵衍生的环状二肽天然产物Polydiscamides B，C和D的第一批合成。这些分子是通过前所未有的天然化学连接-氧化方案，通过环状和线性片段的融合融合而构建的。
• Diastereoselective Allylstannane Additions to (<i>S</i>)-5,6-Dihydro-2<i>H</i>-5-phenyloxazin-2-one. A Concise Synthesis of (<i>S</i>)-β-Methylisoleucine
  作者：Julie A. Pigza、Tadeusz F. Molinski

  DOI：10.1021/ol1001126

  日期：2010.3.19

  The addition of allyl stannanes to (S)-4,5-dihydro-5-phenyl-2H-oxazinone (3) was achieved under Bronsted acid catalysis to give 2-allylmorpholinones with high diastereoselectivity (up to dr 14.2:1). The product of dimethylallyltributylstannane addition to 3 was converted to L-beta-methylisoleucine, an alpha-amino acid residue found in the complex, biologically active marine-derived peptides polytheonamides A and B, and polydiscamides A-C.