methyl 6-oxo-1,7-diazaspiro[4.5]decane-8-carboxylate | 1421067-20-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 6-oxo-1,7-diazaspiro[4.5]decane-8-carboxylate
• 英文别名: Methyl 10-oxo-1,9-diazaspiro[4.5]decane-8-carboxylate
• CAS: 1421067-20-0
• 化学式: C₁₀H₁₆N₂O₃
• 分子量: 212.249
• InChiKey: QDIZYKMLJYKSGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-benzyl 8-methyl 6-oxo-1,7-diazaspiro[4.5]decane-1,8-dicarboxylate 、 1-benzyl 8-methyl 6-oxo-1,7-diazaspiro[4.5]decane-1,8-dicarboxylate 在 硫酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以85%的产率得到methyl 6-oxo-1,7-diazaspiro[4.5]decane-8-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of C8-substituted 4.5-spiro lactams as Glycogen Phosphorylase a inhibitors

  摘要：

  An effective synthesis of 4.5-spiro lactams 28/29, has been completed in nine steps with an overall yield of 5.8%. The 4.5-spiro lactams were made from 2-allyl-Cbz-Pro-OMe 21, which was converted into the corresponding alcohol 22 via a hindered borane reaction with (2-methylbutyl)(2)borane. Subsequent Swern oxidation of 22 gave novel aldehyde 23. Aldehyde 23 was treated under Bucherer-Bergs reaction conditions to give hydantoin 26, which was opened to the corresponding amino acid 30 using di-tert-butyl dicarbonate and DMAP followed by hydrolysis. Treatment of amino acid 30 with acidic methanol gave 4.5-spiro lactams 28/29. Only 4.5-spiro lactam 29 displayed moderate activity against GPa with an IC50 of 241 mu M. (c) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2012.12.004