ethyl 5,7-dinitro-2-oxo-5',6',7',7a'-tetrahydrospiro[indoline-3,3'-pyrrolizine]-2'-carboxylate | 1453811-39-6

• 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: ethyl 5,7-dinitro-2-oxo-5',6',7',7a'-tetrahydrospiro[indoline-3,3'-pyrrolizine]-2'-carboxylate
• 英文别名: ethyl 5,7-dinitro-2-oxospiro[1H-indole-3,3'-5,6,7,8-tetrahydropyrrolizine]-2'-carboxylate
• CAS: 1453811-39-6
• 化学式: C₁₇H₁₆N₄O₇
• 分子量: 388.337
• InChiKey: OCHGLRIREBWJTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  150
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5,7-dinitro-1H-indole-2,3-dione 、 L-脯氨酸 、 丙炔酸乙酯 在 copper(l) iodide 作用下， 以 乙腈 为溶剂， 反应 2.5h， 以85%的产率得到ethyl 5,7-dinitro-2-oxo-5',6',7',7a'-tetrahydrospiro[indoline-3,3'-pyrrolizine]-2'-carboxylate
  参考文献：
  名称：

  Cu-mediated 1,3-dipolar cycloaddition of azomethine ylides with dipolarophiles: a faster access to spirooxindoles of potential pharmacological interest

  摘要：

  CuI facilitated three-component reaction of isatin derivatives, L-proline and terminal alkynes containing an amide or ester functional group. The multi-component reaction (MCR) afforded a faster and practical synthesis of spirooxindole derivatives. A range of novel spirooxindoles were synthesized by using this straightforward and one-pot efficient methodology. A representative compound showed significant inhibition of PDE4B enzyme in vitro and good interactions with this protein in silico. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.126

文献信息

• Cu-mediated 1,3-dipolar cycloaddition of azomethine ylides with dipolarophiles: a faster access to spirooxindoles of potential pharmacological interest
  作者：Shambhu Nath Singh、Sridhar Regati、Abir Kumar Paul、Mohosin Layek、Sarva Jayaprakash、K. Venkateshwara Reddy、Girdhar Singh Deora、Soumita Mukherjee、Manojit Pal

  DOI：10.1016/j.tetlet.2013.07.126

  日期：2013.10

  CuI facilitated three-component reaction of isatin derivatives, L-proline and terminal alkynes containing an amide or ester functional group. The multi-component reaction (MCR) afforded a faster and practical synthesis of spirooxindole derivatives. A range of novel spirooxindoles were synthesized by using this straightforward and one-pot efficient methodology. A representative compound showed significant inhibition of PDE4B enzyme in vitro and good interactions with this protein in silico. (C) 2013 Elsevier Ltd. All rights reserved.