tert-butyl (3S)-4-methyl-1,9-dioxo-3-propan-2-yl-3H-pyrrolo[3,4-b]quinoline-2-carboxylate | 1042980-74-4

• 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: tert-butyl (3S)-4-methyl-1,9-dioxo-3-propan-2-yl-3H-pyrrolo[3,4-b]quinoline-2-carboxylate
• CAS: 1042980-74-4
• 化学式: C₂₀H₂₄N₂O₄
• 分子量: 356.422
• InChiKey: XENZPGVSRISFKP-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S)-4-methyl-1,9-dioxo-3-propan-2-yl-3H-pyrrolo[3,4-b]quinoline-2-carboxylate 在 zinc dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以94%的产率得到quinolactacin B
  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：

  tert-butyl (3S)-1-hydroxy-4-methyl-9-oxo-3-propan-2-yl-1,3-dihydropyrrolo[3,4-b]quinoline-2-carboxylate 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以67 mg的产率得到tert-butyl (3S)-4-methyl-1,9-dioxo-3-propan-2-yl-3H-pyrrolo[3,4-b]quinoline-2-carboxylate
  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