(3R,4S,8aS)-3,4-diphenyl-3,4,6,7,8,8a-hexahydro(313C)pyrrolo[2,1-c](213C)[1,4]oxazin-1-one | 1196980-37-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (3R,4S,8aS)-3,4-diphenyl-3,4,6,7,8,8a-hexahydro(313C)pyrrolo[2,1-c](213C)[1,4]oxazin-1-one
• CAS: 1196980-37-6
• 化学式: C₁₉H₁₉NO₂
• 分子量: 295.343
• InChiKey: UORBQXHZUPMAKQ-OGOVMUQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4S,8aS)-3,4-diphenyl-3,4,6,7,8,8a-hexahydro(313C)pyrrolo[2,1-c](213C)[1,4]oxazin-1-one 在 10% palladium on carbon 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 21.5h， 以78%的产率得到[1,3-⁽¹³⁾C₂]-L-proline
  参考文献：
  名称：

  Enantioselective Syntheses of α-Fmoc-Pbf-[2-¹³C]-l-arginine and Fmoc-[1,3-¹³C₂]-l-proline and Incorporation into the Neurotensin Receptor 1 Ligand, NT₈₋₁₃

  摘要：

  Enantioselective syntheses of selectively labeled, orthogonally protected [2-C-13]L-arginine and [1,3-C-13(2)]-L-proline are described from the commercially available precursors [2-C-13]bromoacetic acid and potassium [C-13]cyanide, Interestingly the enhanced signal assigned to C-2 in the C-13 NMR spectrum of alpha-Fmoc-Pbf-[2-C-13]-L-arginine was very broad at room temperature. The two Fmoc-labeled amino acids were used to prepare [2-C-13]-Arg9 and [1,3-C-13(2)]-Pro 10 labeled ligand (NT8-13) by manual Fmoc-SPSS.

  DOI：

  10.1021/jo9014497
• 作为产物：
  描述：

  tert-butyl (3S,5S,6R)-3-[3-(4-methylphenyl)sulfonyloxy(113C)propyl]-2-oxo-5,6-diphenyl-(213C)1,4-oxazinane-4-carboxylate 在 三氟乙酸 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.58h， 以63%的产率得到(3R,4S,8aS)-3,4-diphenyl-3,4,6,7,8,8a-hexahydro(313C)pyrrolo[2,1-c](213C)[1,4]oxazin-1-one
  参考文献：
  名称：

  Enantioselective Syntheses of α-Fmoc-Pbf-[2-¹³C]-l-arginine and Fmoc-[1,3-¹³C₂]-l-proline and Incorporation into the Neurotensin Receptor 1 Ligand, NT₈₋₁₃

  摘要：

  Enantioselective syntheses of selectively labeled, orthogonally protected [2-C-13]L-arginine and [1,3-C-13(2)]-L-proline are described from the commercially available precursors [2-C-13]bromoacetic acid and potassium [C-13]cyanide, Interestingly the enhanced signal assigned to C-2 in the C-13 NMR spectrum of alpha-Fmoc-Pbf-[2-C-13]-L-arginine was very broad at room temperature. The two Fmoc-labeled amino acids were used to prepare [2-C-13]-Arg9 and [1,3-C-13(2)]-Pro 10 labeled ligand (NT8-13) by manual Fmoc-SPSS.

  DOI：

  10.1021/jo9014497