1-(2-bromo-acetyl)-5-methoxy-7-oxo-8-phenyl-1,3,4,7,8,8a-hexahydro-2H-quinoline-4a-carboxylic acid methyl ester

• 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-(2-bromo-acetyl)-5-methoxy-7-oxo-8-phenyl-1,3,4,7,8,8a-hexahydro-2H-quinoline-4a-carboxylic acid methyl ester
• 英文别名: methyl (4aS,8aR)-1-(2-bromoacetyl)-5-methoxy-7-oxo-8-phenyl-3,4,8,8a-tetrahydro-2H-quinoline-4a-carboxylate
• 化学式: C₂₀H₂₂BrNO₅
• 分子量: 436.302
• InChiKey: KSYSUSOREKWASB-PGDXBAMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-bromo-acetyl)-5-methoxy-7-oxo-8-phenyl-1,3,4,7,8,8a-hexahydro-2H-quinoline-4a-carboxylic acid methyl ester 在 potassium tert-butylate 作用下， 以 苯 为溶剂， 反应 4.5h， 以99%的产率得到7-methoxy-2,9-dioxo-9a-phenyl-1,2,5,6,9a,9b-hexahydro-4H,9H-pyrrolo[3,2,1-ij]quinoline-6a-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of the tricyclic core structure of vindoline

  摘要：

  An efficient synthesis of the core tricyclic structure (18) of vindoline has been achieved using the strategy, which features an intramolecular 1,3-dipolar cycloaddition of the azido dienone (12) to give aziridine (13) with complete region- and stereocontrol. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.115
• 作为产物：
  描述：

  6-methoxy-4-oxo-3b-phenyl-2,3,3b,6b-tetrahydro-1H,4H-3a-aza-cyclopropa[de]naphthalene-6a-carboxylic acid methyl ester 在 lithium 、 碳酸氢钠 作用下， 以 四氢呋喃 、 氨 、 溶剂黄146 为溶剂， 反应 0.5h， 生成 1-(2-bromo-acetyl)-5-methoxy-7-oxo-8-phenyl-1,3,4,7,8,8a-hexahydro-2H-quinoline-4a-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of the tricyclic core structure of vindoline

  摘要：

  An efficient synthesis of the core tricyclic structure (18) of vindoline has been achieved using the strategy, which features an intramolecular 1,3-dipolar cycloaddition of the azido dienone (12) to give aziridine (13) with complete region- and stereocontrol. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.115

文献信息

• Synthesis of the tricyclic core structure of vindoline
  作者：Zihong Guo、Arthur G. Schultz

  DOI：10.1016/j.tetlet.2003.11.115

  日期：2004.1

  An efficient synthesis of the core tricyclic structure (18) of vindoline has been achieved using the strategy, which features an intramolecular 1,3-dipolar cycloaddition of the azido dienone (12) to give aziridine (13) with complete region- and stereocontrol. (C) 2003 Elsevier Ltd. All rights reserved.