methyl 2-(3-(2-(ethoxycarbonylamino)ethyl)-5-methyl-1H-indol-2-yl)acetate | 1449683-71-9

• 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: methyl 2-(3-(2-(ethoxycarbonylamino)ethyl)-5-methyl-1H-indol-2-yl)acetate
• 英文别名: ethyl 2-(3-(2-(ethoxycarbonylamino)ethyl)-5-methyl-1H-indol-2-yl)acetate；methyl 2-[3-[2-(ethoxycarbonylamino)ethyl]-5-methyl-1H-indol-2-yl]acetate
• CAS: 1449683-71-9
• 化学式: C₁₇H₂₂N₂O₄
• 分子量: 318.373
• InChiKey: KUJUOGXPTMJVMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(3-(2-(ethoxycarbonylamino)ethyl)-5-methyl-1H-indol-2-yl)acetate 、 丙烯醛 在 邻硝基苯甲酸 、 quinidine 作用下， 以 乙酸乙酯 为溶剂， 反应 8.0h， 以87%的产率得到(S)-methyl 4a-(2-(ethoxycarbonylamino)ethyl)-6-methyl-4a,9-dihydro-4H-carbazole-1-carboxylate
  参考文献：
  名称：

  Enantioselective Intermolecular Formal [3 + 3] Cycloaddition of 2,3-Disubstituted Indoles with Acrolein

  摘要：

  An expedient enantioselective synthesis of highly substituted hydrocarbazoles has been realized by an organocatalyzed formal [3 + 3] cycloaddition between acrolein and 2,3-disubstituted indoles. Tricyclic hydrocarbazoles were obtained from a broad range of 2,3-disubstituted indoles and acrolein in good to excellent yields and excellent enantioselectivites.

  DOI：

  10.1021/ol401809d
• 作为产物：
  描述：

  methyl 2-((ethoxycarbonothioyl)thio)acetate 、 在 过氧化双月桂酰 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 methyl 2-(3-(2-(ethoxycarbonylamino)ethyl)-5-methyl-1H-indol-2-yl)acetate
  参考文献：
  名称：

  Enantioselective Intermolecular Formal [3 + 3] Cycloaddition of 2,3-Disubstituted Indoles with Acrolein

  摘要：

  An expedient enantioselective synthesis of highly substituted hydrocarbazoles has been realized by an organocatalyzed formal [3 + 3] cycloaddition between acrolein and 2,3-disubstituted indoles. Tricyclic hydrocarbazoles were obtained from a broad range of 2,3-disubstituted indoles and acrolein in good to excellent yields and excellent enantioselectivites.

  DOI：

  10.1021/ol401809d

文献信息

• Enantioselective Michael/aza-Michael/Cyclization Organocascade to Tetracyclic Spiroindolines: Concise Total Synthesis of Kopsinine and Aspidofractine
  作者：Xiaoyu Wu、Jianbiao Huang、Beibei Guo、Long Zhao、Yong Liu、Jie Chen、Weiguo Cao

  DOI：10.1002/adsc.201400363

  日期：2014.11.3

  AbstractKopsinine and related alkaloids are attractive synthetic targets because of their structural complexity and biological activities. An organocatalytic Michael addition/aza‐Michael addition/cyclization cascade sequence has been developed for the enantioselective preparation of tetracyclic spiroindolines from 2,3‐disubstituted indoles and propargyl aldehyde in moderate to good yields and good to excellent enantioselectivities. The synthetic value of these advanced structures has been demonstrated by the synthesis of kopsinine and related alkaloids. Key steps for the concise synthesis of these alkaloids included an efficient enantioselective construction of tetracyclic spiroindolines bearing a dienamino ester moiety and the organocatalyzed nucleophilic addition of a dienamino ester to acrolein.magnified image