(S)-4-methyl-7,8,9,9a-tetrahydro-1H-quinolizin-2(6H)-one | 1240530-54-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (S)-4-methyl-7,8,9,9a-tetrahydro-1H-quinolizin-2(6H)-one
• 英文别名: (9aS)-4-methyl-1,6,7,8,9,9a-hexahydroquinolizin-2-one
• CAS: 1240530-54-4
• 化学式: C₁₀H₁₅NO
• 分子量: 165.235
• InChiKey: BTRTYHMKVXOHRD-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl (2S)-2-(4-chlorobutyl)-6-methyl-4-oxo-2,3-dihydropyridine-1-carboxylate 在 叔丁胺 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到(S)-4-methyl-7,8,9,9a-tetrahydro-1H-quinolizin-2(6H)-one
  参考文献：
  名称：

  格氏试剂对4-甲氧基吡啶鎓离子的对映选择性催化脱芳加成

  摘要：

  我们描述了使用格氏试剂对吡啶衍生物进行对映选择性脱芳基化烷基化的通用催化方法，允许直接获得接近对映纯的手性二氢-4-吡啶酮，产率高达 98%。该方法涉及原位形成的N-酰基吡啶盐的脱芳构化，使用烷基有机镁试剂作为亲核试剂和手性铜 (I) 配合物作为催化剂。计算和机理研究提供了对催化过程反应性和对映选择性起源的见解。

  DOI：

  10.1021/acscatal.1c01544

文献信息

• Synthesis of 6- and 7-Membered Cyclic Enaminones: Scope and Mechanism
  作者：Micah J. Niphakis、Brandon J. Turunen、Gunda I. Georg

  DOI：10.1021/jo100907u

  日期：2010.10.15

  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).