4-methyl 1'-((1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-cyclohexyl) 2,2-dimethyl-2',3-dioxospiro[cyclopentan-1,3'-indoline]-1',4-dicarboxylate

• 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: 4-methyl 1'-((1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-cyclohexyl) 2,2-dimethyl-2',3-dioxospiro[cyclopentan-1,3'-indoline]-1',4-dicarboxylate
• 英文别名: 1-O-methyl 1-O'-[(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (4S)-3,3-dimethyl-2,2'-dioxospiro[cyclopentane-4,3'-indole]-1,1'-dicarboxylate
• 化学式: C₃₃H₃₉NO₆
• 分子量: 545.676
• InChiKey: GYIAAQDTINKXPK-LCOHACJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-methyl 1'-((1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-cyclohexyl) 2,2-dimethyl-2',3-dioxospiro[cyclopentan-1,3'-indoline]-1',4-dicarboxylate 、 三氟甲磺酸酐 在 双(三甲基硅烷基)氨基钾 作用下， 以 甲苯 为溶剂， 反应 2.33h， 以76%的产率得到4-methyl 1'-((1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-cyclohexyl) 2,2-dimethyl-2'-oxo-3-(trifluoromethylsulfonyloxy)spiro[cyclopent[3]en-1,3'-indoline]-1',4-dicarboxylate
  参考文献：
  名称：

  Concise, Stereoselective Approach to the Spirooxindole Ring System of Citrinadin A

  摘要：

  The spirooxindole ring system of citrinadin A has been synthesized with excellent control over the absolute stereochemistry at the spirocenter. The key step involves a novel diastereoselective DMDO-mediated oxidative rearrangement employing an 8-phenylmenthol chiral auxiliary on the indole nitrogen.

  DOI：

  10.1021/ol702132v
• 作为产物：
  描述：

  (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-cyclohexyl 2,2-dimethyl-2,3'-dioxospiro[cyclopentan-1,3'-indoline]-1'-carboxylate 、 氰基甲酸甲酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.33h， 以80%的产率得到4-methyl 1'-((1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-cyclohexyl) 2,2-dimethyl-2',3-dioxospiro[cyclopentan-1,3'-indoline]-1',4-dicarboxylate
  参考文献：
  名称：

  Concise, Stereoselective Approach to the Spirooxindole Ring System of Citrinadin A

  摘要：

  The spirooxindole ring system of citrinadin A has been synthesized with excellent control over the absolute stereochemistry at the spirocenter. The key step involves a novel diastereoselective DMDO-mediated oxidative rearrangement employing an 8-phenylmenthol chiral auxiliary on the indole nitrogen.

  DOI：

  10.1021/ol702132v

文献信息

• Concise, Stereoselective Approach to the Spirooxindole Ring System of Citrinadin A
  作者：Martin Pettersson、Daniel Knueppel、Stephen F. Martin

  DOI：10.1021/ol702132v

  日期：2007.10.1

  The spirooxindole ring system of citrinadin A has been synthesized with excellent control over the absolute stereochemistry at the spirocenter. The key step involves a novel diastereoselective DMDO-mediated oxidative rearrangement employing an 8-phenylmenthol chiral auxiliary on the indole nitrogen.