8-O-benzyl 4-O-methyl 2-ethyl-3-oxo-2,8-diazaspiro[4.5]deca-6,9-diene-4,8-dicarboxylate | 1235457-37-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 8-O-benzyl 4-O-methyl 2-ethyl-3-oxo-2,8-diazaspiro[4.5]deca-6,9-diene-4,8-dicarboxylate
• CAS: 1235457-37-0
• 化学式: C₂₀H₂₂N₂O₅
• 分子量: 370.405
• InChiKey: NSWRLGDWFLMTBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Methyl 3-[ethyl(pyridin-4-ylmethyl)amino]-3-oxopropanoate 、 氯甲酸苄酯 在 titanium(IV) isopropylate 作用下， 以 二氯甲烷 为溶剂， 反应 0.11h， 以86%的产率得到8-O-benzyl 4-O-methyl 2-ethyl-3-oxo-2,8-diazaspiro[4.5]deca-6,9-diene-4,8-dicarboxylate
  参考文献：
  名称：

  Titanium-Mediated Spirocyclization Reactions of 4-Alkylpyridines

  摘要：

  Pyridines substituted at the 4-position with alkyl tethers containing beta-dicarbonyl moieties were converted to spirocyclic 4,4-disubstituted dihydropyridines. Optimal conditions for these transformations involved N-acylation of the pyridine substrate with a chloroformate electrophile in the presence of Ti((OPr)-Pr-i)(4). Cyclization products could be easily converted into spiro-piperidine derivatives or elaborated into more complex heterocyclic frameworks via Au-catalyzed cycloisomerization.

  DOI：

  10.1021/ol1012636

文献信息

• Titanium-Mediated Spirocyclization Reactions of 4-Alkylpyridines
  作者：Sharavathi G. Parameswarappa、F. Christopher Pigge

  DOI：10.1021/ol1012636

  日期：2010.8.6

  Pyridines substituted at the 4-position with alkyl tethers containing beta-dicarbonyl moieties were converted to spirocyclic 4,4-disubstituted dihydropyridines. Optimal conditions for these transformations involved N-acylation of the pyridine substrate with a chloroformate electrophile in the presence of Ti((OPr)-Pr-i)(4). Cyclization products could be easily converted into spiro-piperidine derivatives or elaborated into more complex heterocyclic frameworks via Au-catalyzed cycloisomerization.