(R)-3-(but-3-enyl)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one | 1160107-32-3

• 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: (R)-3-(but-3-enyl)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one
• 英文别名: (3R)-5-but-3-enyl-3-phenyl-2,3-dihydro-1,4-oxazin-6-one
• CAS: 1160107-32-3
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: WYPLEMBFQPRZOZ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  (R)-3-(but-3-enyl)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 氯化亚砜 、 potassium tert-butylate 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.67h， 生成 (R)-1-azaspiro[4.5]dec-7-ene-2,4-dione
  参考文献：
  名称：

  Spirocycles as Rigidified sp³-Rich Scaffolds for a Fragment Collection

  摘要：

  Novel divergent methodology to access sp³-rich spirocyclic fragments is reported. First, a robust modular synthesis of bis-alkene amino ester building blocks was developed. Three different carbocycles and six heterocycles were then constructed to assemble eight spirocycles. Importantly, strategic exit vectors were incorporated within each scaffold to aid fragment growth and were elaborated via chemical modifications. Finally, computational methods demonstrate higher levels of rigidity, three-dimensionality, and structural diversity of the library compared to a commercial collection.

  DOI：

  10.1021/acs.orglett.9b01499
• 作为产物：
  描述：

  D-苯甘氨醇 、 2-氧代-5-己酸乙酯 以 2,2,2-三氟乙醇 为溶剂， 反应 0.75h， 以55%的产率得到(R)-3-(but-3-enyl)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one
  参考文献：
  名称：

  立体肽的直接立体选择访问。

  摘要：

  描述了由衍生自（R）-苯基甘醇的手性亚氨基内酯制备环状二肽模拟物。合成途径的关键步骤包括完全立体选择性地构建四元中心，通过RCM环化形成六元，七元或八元内酰胺，以及在内酰胺环内引入新的氨基。还报道了三肽模拟物的合成。

  DOI：

  10.1021/jo900679c

文献信息

• Straightforward Stereoselective Access to Cyclic Peptidomimetics
  作者：Santos Fustero、Natalia Mateu、Laia Albert、José Luis Aceña

  DOI：10.1021/jo900679c

  日期：2009.6.5

  steps of the synthetic route included the fully stereoselective construction of a quaternary center, the formation of six-, seven-, or eight-membered lactams by means of an RCM cyclization, and the introduction of a new amino group within the lactam ring. The synthesis of a tripeptide mimetic is also reported.

  描述了由衍生自（R）-苯基甘醇的手性亚氨基内酯制备环状二肽模拟物。合成途径的关键步骤包括完全立体选择性地构建四元中心，通过RCM环化形成六元，七元或八元内酰胺，以及在内酰胺环内引入新的氨基。还报道了三肽模拟物的合成。
• Spirocycles as Rigidified sp³-Rich Scaffolds for a Fragment Collection
  作者：Attila Sveiczer、Andrew J. P. North、Natalia Mateu、Sarah L. Kidd、Hannah F. Sore、David R. Spring

  DOI：10.1021/acs.orglett.9b01499

  日期：2019.6.21

  Novel divergent methodology to access sp³-rich spirocyclic fragments is reported. First, a robust modular synthesis of bis-alkene amino ester building blocks was developed. Three different carbocycles and six heterocycles were then constructed to assemble eight spirocycles. Importantly, strategic exit vectors were incorporated within each scaffold to aid fragment growth and were elaborated via chemical modifications. Finally, computational methods demonstrate higher levels of rigidity, three-dimensionality, and structural diversity of the library compared to a commercial collection.