(S)-4-phenyl-7,8,9,9a-tetrahydro-1H-quinolizin-2(6H)-one | 1240530-55-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹嗪类
• 英文名称: (S)-4-phenyl-7,8,9,9a-tetrahydro-1H-quinolizin-2(6H)-one
• CAS: 1240530-55-5
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: DIWZFDLGSDGGTH-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  tert-butyl (S)-2-(2-oxo-4-phenylbut-3-yn-1-yl)piperidine-1-carboxylate 在 甲酸 、 sodium iodide 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 30.0h， 生成 (R)-4-phenyl-7,8,9,9a-tetrahydro-1H-quinolizin-2(6H)-one 、 (S)-4-phenyl-7,8,9,9a-tetrahydro-1H-quinolizin-2(6H)-one
  参考文献：
  名称：

  Synthesis of 6- and 7-Membered Cyclic Enaminones: Scope and Mechanism

  摘要：

  Six- and seven-membered cyclic enaminones can be prepared using common. environmentally benign reagents. Ammo acids are used as synthetic precursors allowing diversification and the incorporation of chirality The key reaction in this multistep process involves deprotection Boc-amino ynones and subsequent treatment with methanolic K2CO3 to induce cyclization. A beta-amino elimination side reaction was identified in a few labile substrates that led to loss of stereochemical purity of degradation. This process can be mitigated in specific cases using mild deprotection conditions NMR and deuteitum-labeling experiments provided valuable insight into the work kings and limitations of this reaction Although disguised as a 6-endo-dig cyclization, the reagents employed in the transformation play a direct role in bond-making and bond-breaking. thus changing die mode of addition to a 6-endo-trig cyclization This method can be used to construct an array of monocyclic and bicyclic scaffolds. many of which me found in well-known natural products (e g indolizidine, quinolizidine, and Stemona alkaloids).

  DOI：

  10.1021/jo100907u