1'-tert-butyl 5-methyl (1S,2R,4S,5S)-2-ethyl-2-hydroxy-4-nitro-2'-oxospiro[cyclopentane-1,3'-indoline]-1',5-dicarboxylate | 1449336-76-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1'-tert-butyl 5-methyl (1S,2R,4S,5S)-2-ethyl-2-hydroxy-4-nitro-2'-oxospiro[cyclopentane-1,3'-indoline]-1',5-dicarboxylate
• 英文别名: 1-O'-tert-butyl 1-O-methyl (1S,2S,3R,5S)-3-ethyl-3-hydroxy-5-nitro-2'-oxospiro[cyclopentane-2,3'-indole]-1,1'-dicarboxylate
• CAS: 1449336-76-8
• 化学式: C₂₁H₂₆N₂O₈
• 分子量: 434.446
• InChiKey: WEAFJAIFRNABAA-YJPXFSGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-戊烯-3-酮 在 C₃₅H₄₈N₄OS 、 溶剂黄146 、 sodium nitrite 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1'-tert-butyl 5-methyl 2-ethyl-2-hydroxy-4-nitro-2'-oxospiro[cyclopentane-1,3'-indoline]-1',5-dicarboxylate 、 1'-tert-butyl 5-methyl (1S,2R,4S,5S)-2-ethyl-2-hydroxy-4-nitro-2'-oxospiro[cyclopentane-1,3'-indoline]-1',5-dicarboxylate
  参考文献：
  名称：

  Asymmetric Synthesis of Congested Spiro-cyclopentaneoxindoles via an Organocatalytic Cascade Reaction

  摘要：

  Starting from simple alkylidene oxindoles and nitroketones, a highly stereoselective methodology was developed for the synthesis of spiro-cyclopentaneoxindoles with four consecutive stereogenic centers. Using an organocatalytic cascade of Michael and aldol reactions in the presence of a chiral thiourea catalyst products were obtained in moderate to high yields and excellent enantioselectivities. Nitro, ester, and hydroxyl groups were introduced to the spiro ring, which could be used to facilitate further functionalization of the products.

  DOI：

  10.1021/jo4008223