2-((6-methoxynaphthalen-2-yl)ethynyl)-1-(4-nitrobenzyl)pyrrolidine | 1206905-59-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-((6-methoxynaphthalen-2-yl)ethynyl)-1-(4-nitrobenzyl)pyrrolidine
• 英文别名: 1-(4-nitrobenzyl)-2-(2-(2-methoxynaphthalen-6-yl)ethynyl)pyrrolidine；2-[2-(6-Methoxynaphthalen-2-yl)ethynyl]-1-[(4-nitrophenyl)methyl]pyrrolidine
• CAS: 1206905-59-0
• 化学式: C₂₄H₂₂N₂O₃
• 分子量: 386.45
• InChiKey: DIFMQJQQBNCGNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-乙炔基-6-甲氧基萘 、 对硝基苯甲醛 、 DL-脯氨酸 在 copper(l) iodide 作用下， 以 甲苯 为溶剂， 反应 0.17h， 以65%的产率得到2-((6-methoxynaphthalen-2-yl)ethynyl)-1-(4-nitrobenzyl)pyrrolidine
  参考文献：
  名称：

  Aldehyde- and Ketone-Induced Tandem Decarboxylation-Coupling (Csp³−Csp) of Natural α-Amino Acids and Alkynes

  摘要：

  An interesting aldehyde- and ketone-induced intermolecular tandem decarboxylation-coupling (Csp(3)-Csp) catalyzed by copper with use of natural alpha-amino acids as starting materials is developed under neutral conditions with the production of CO2 and H2O as the only by products. Various functionalized nitrogen-containing compounds were obtained by this method. In these processes, interesting regioselectivites of the alkylation were observed, which has been rationalized by the relative stability of proposed resonance structures based on computation methods.

  DOI：

  10.1021/jo902319h

文献信息

• New routes towards azomethine ylide generation from prolines to synthesize diverseN-heterocycles: a DFT supportedendo-selective mechanism
  作者：Radha M. Laha、Shobhon Aich、Ankan Kumar Sarkar、Tanmoy Dutta、Narendra Nath Ghosh、Saikat Khamarui、Dilip K. Maiti

  DOI：10.1039/d4ob01004c

  日期：——

  Azomethine ylides are generated using either organocatalysts or metal catalysts via a ballet of decarboxylative C–N coupling choreographed by prolines. These strategies enable diastereoselective [3 + 2] cycloaddition, C–C coupling, and ring annulation, providing sustainable routes. The synthesized pyrrolizines and other heterocycles have potential applications in the development of crucial biomolecules

  甲亚胺叶立德是使用有机催化剂或金属催化剂，通过脯氨酸精心设计的脱羧 C-N 偶联生成的。这些策略可实现非对映选择性 [3 + 2] 环加成、C-C 偶联和环化，从而提供可持续的路线。合成的吡咯嗪和其他杂环化合物在关键生物分子和药物的开发中具有潜在的应用。偶氮甲碱叶立德的内选择性是通过 DFT 计算实现和支持的。