(3R, 8aS)-hexahydro-8a-(4-methoxyphenyl)-3-phenyloxazolo[3,2-a]pyrazin-5-one | 1399859-37-0

• 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, 8aS)-hexahydro-8a-(4-methoxyphenyl)-3-phenyloxazolo[3,2-a]pyrazin-5-one
• CAS: 1399859-37-0
• 化学式: C₁₉H₂₀N₂O₃
• 分子量: 324.379
• InChiKey: CTNVTEFJZISYIO-PKOBYXMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  50.8
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3R, 8aS)-hexahydro-8a-(4-methoxyphenyl)-3-phenyloxazolo[3,2-a]pyrazin-5-one 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 、
  参考文献：
  名称：

  Stereoselective synthesis of enantiopure N-protected-3-arylpiperazines from keto-esters

  摘要：

  An efficient method for a stereoselective synthesis of optically pure N-Boc-3-arylpiperazines has been developed. After optimization of the protecting group strategy and experimental conditions, compounds were obtained via a highly stereoselective synthesis in up to 45% overall yield. This is a practical route to optically pure piperazines for medicinal chemistry. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.031
• 作为产物：
  描述：

  (3R, 8aS)-benzylhexahydro-8a-(4-methoxyphenyl)-5-oxo-3-phenyloxazolo[3,2-a]pyrazine-7-carboxylate 在 20% Pd/C 、 氢气 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以87%的产率得到(3R, 8aS)-hexahydro-8a-(4-methoxyphenyl)-3-phenyloxazolo[3,2-a]pyrazin-5-one
  参考文献：
  名称：

  Stereoselective synthesis of enantiopure N-protected-3-arylpiperazines from keto-esters

  摘要：

  An efficient method for a stereoselective synthesis of optically pure N-Boc-3-arylpiperazines has been developed. After optimization of the protecting group strategy and experimental conditions, compounds were obtained via a highly stereoselective synthesis in up to 45% overall yield. This is a practical route to optically pure piperazines for medicinal chemistry. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.031

文献信息

• Efficient, Stereoselective Synthesis of Oxazolo[3,2-<i>a</i>]pyrazin-5-ones:  Novel Bicyclic Lactam Scaffolds from the Bicyclocondensation of 3-Aza-1,5-ketoacids and Amino Alcohols
  作者：Josef R. Bencsik、Timothy Kercher、Michael O'Sulliva、John A. Josey

  DOI：10.1021/ol030065h

  日期：2003.7.1

  [reaction: see text] The bicyclocondensation of 3-aza-1,5-ketoacids and amino alcohols furnished novel oxazolo[3,2-a]pyrazin-5-one scaffolds possessing angular, ring junction substituents in high yield with excellent levels of substrate-based diastereocontrol. Mild oxidation of serinol-derived scaffolds provided access to a new class of constrained dipeptide surrogates. Deprotection of the endocyclic

  [反应：见正文] 3-氮杂-1,5-酮酸和氨基醇的双环缩合反应提供了新颖的恶唑并[3,2-a]吡嗪-5-酮支架，该支架具有高产率的角，环连接取代基，且具有极好的环磷酰胺水平基于底物的非对映控制。丝氨酸衍生的支架的轻度氧化提供了一种新的受约束的二肽替代物。这些支架中所含的内环胺的脱保护作用允许通过N-官能化进一步多样化。