1-(S)-isopropyl-9-oxo-1,3,4,9-tetrahydropyrrolo[3,4-b]-quinoline-2-carboxylic acid tert-butyl ester | 1043876-92-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-(S)-isopropyl-9-oxo-1,3,4,9-tetrahydropyrrolo[3,4-b]-quinoline-2-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (3S)-9-oxo-3-propan-2-yl-3,4-dihydro-1H-pyrrolo[3,4-b]quinoline-2-carboxylate
• CAS: 1043876-92-1
• 化学式: C₁₉H₂₄N₂O₃
• 分子量: 328.411
• InChiKey: IYQJVGQUSNLQGY-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(S)-isopropyl-9-oxo-1,3,4,9-tetrahydropyrrolo[3,4-b]-quinoline-2-carboxylic acid tert-butyl ester 、 碘甲烷 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以90%的产率得到1-(S)-isopropyl-4-methyl-9-oxo-1,3,4,9-tetrahydropyrrolo[3,4-b]-quinoline-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Enantioselective total synthesis of (S)-(−)-quinolactacin B

  摘要：

  The enantioselective total synthesis of (-)-quinolactacin B (-)-1 was performed in seven steps and 33% overall yield from tryptamine. The synthesis features the use of ruthenium catalytic asymmetric hydrogen reaction to introduce the chirality in dihydro-beta-carboline 2. Based on Noyori's work, the hydrogenation using the (R,R)-TsDPEN-Ru complex produces dihydro-beta-carbolines possessing the (S) absolute configuration, the corrected asymmetric center of the natural product. The synthetic quinolactacin B displayed optical rotations that was in accordance with that of the natural product, thereby supporting the (S) configuration for natural quinolactacin B. The final product's stereochemical assignment is in agreement with that proposed by Nakagawa and co-workers. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.04.130
• 作为产物：
  描述：

  1-(S)-isopropyl-1,3,4,9-tetrahydro-β-carboline-2-carboxylic acid tert-butyl ester 在 18-冠醚-6 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 1-(S)-isopropyl-9-oxo-1,3,4,9-tetrahydropyrrolo[3,4-b]-quinoline-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Enantioselective total synthesis of (S)-(−)-quinolactacin B

  摘要：

  The enantioselective total synthesis of (-)-quinolactacin B (-)-1 was performed in seven steps and 33% overall yield from tryptamine. The synthesis features the use of ruthenium catalytic asymmetric hydrogen reaction to introduce the chirality in dihydro-beta-carboline 2. Based on Noyori's work, the hydrogenation using the (R,R)-TsDPEN-Ru complex produces dihydro-beta-carbolines possessing the (S) absolute configuration, the corrected asymmetric center of the natural product. The synthetic quinolactacin B displayed optical rotations that was in accordance with that of the natural product, thereby supporting the (S) configuration for natural quinolactacin B. The final product's stereochemical assignment is in agreement with that proposed by Nakagawa and co-workers. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.04.130

文献信息

• Enantioselective total synthesis of (S)-(−)-quinolactacin B
  作者：Nagula Shankaraiah、Wender A. da Silva、Carlos Kleber Z. Andrade、Leonardo Silva Santos

  DOI：10.1016/j.tetlet.2008.04.130

  日期：2008.6

  The enantioselective total synthesis of (-)-quinolactacin B (-)-1 was performed in seven steps and 33% overall yield from tryptamine. The synthesis features the use of ruthenium catalytic asymmetric hydrogen reaction to introduce the chirality in dihydro-beta-carboline 2. Based on Noyori's work, the hydrogenation using the (R,R)-TsDPEN-Ru complex produces dihydro-beta-carbolines possessing the (S) absolute configuration, the corrected asymmetric center of the natural product. The synthetic quinolactacin B displayed optical rotations that was in accordance with that of the natural product, thereby supporting the (S) configuration for natural quinolactacin B. The final product's stereochemical assignment is in agreement with that proposed by Nakagawa and co-workers. (C) 2008 Elsevier Ltd. All rights reserved.