6-bromo-4-<2-(tert-butoxycarbonyl)amino>-5,8-dimethoxyquinoline | 133400-98-3

• 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: 6-bromo-4-<2-(tert-butoxycarbonyl)amino>-5,8-dimethoxyquinoline
• 英文别名: tert-butyl N-[2-(6-bromo-5,8-dimethoxyquinolin-4-yl)phenyl]carbamate
• CAS: 133400-98-3
• 化学式: C₂₂H₂₃BrN₂O₄
• 分子量: 459.34
• InChiKey: QABOKOFIWROARI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-bromo-4-<2-(tert-butoxycarbonyl)amino>-5,8-dimethoxyquinoline 在 ammonium cerium(IV) nitrate 、 硫酸 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 18.0h， 生成 6-bromo-4-<2-<(trifluoroacetyl)amino>-phenyl>quinoline-5,8-dione
  参考文献：
  名称：

  Synthesis of isoascididemin, a regioisomer of the marine alkaloid ascididemin

  摘要：

  The synthesis of isoascididemin, a regioisomer of the naturally occurring ascididemin, has been completed in nine steps from 2,5-dimethoxyaniline. The key steps feature a selective palladium(O)-catalyzed cross-coupling reaction of 6-bromo-5,8-dimethoxy-4-[(trifluoromethanesulfonyl)oxy]quinoline with N-(tert-butoxycarbonyl)-2-(trimethylstannyl)aniline promoted by Cu(I) and a hetero-Diels-Alder reaction of a quinoline-5,8-dione with acrolein N,N-dimethylhydrazone.

  DOI：

  10.1021/jo00011a011
• 作为产物：
  描述：

  6-bromo-5,8-dimethoxy-4(1H)-quinolinone 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 lithium chloride 、 copper(I) bromide 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 6-bromo-4-<2-(tert-butoxycarbonyl)amino>-5,8-dimethoxyquinoline
  参考文献：
  名称：

  Synthesis of isoascididemin, a regioisomer of the marine alkaloid ascididemin

  摘要：

  The synthesis of isoascididemin, a regioisomer of the naturally occurring ascididemin, has been completed in nine steps from 2,5-dimethoxyaniline. The key steps feature a selective palladium(O)-catalyzed cross-coupling reaction of 6-bromo-5,8-dimethoxy-4-[(trifluoromethanesulfonyl)oxy]quinoline with N-(tert-butoxycarbonyl)-2-(trimethylstannyl)aniline promoted by Cu(I) and a hetero-Diels-Alder reaction of a quinoline-5,8-dione with acrolein N,N-dimethylhydrazone.

  DOI：

  10.1021/jo00011a011

文献信息

• GOMEZ-BENGOA, ENRIQUE;ECHAVARREN, ANTONIO M., J. ORG. CHEM., 56,(1991) N1, C. 3497-3501
  作者：GOMEZ-BENGOA, ENRIQUE、ECHAVARREN, ANTONIO M.

  DOI：——

  日期：——
• Synthesis of isoascididemin, a regioisomer of the marine alkaloid ascididemin
  作者：Enrique Gomez-Bengoa、Antonio M. Echavarren

  DOI：10.1021/jo00011a011

  日期：1991.5

  The synthesis of isoascididemin, a regioisomer of the naturally occurring ascididemin, has been completed in nine steps from 2,5-dimethoxyaniline. The key steps feature a selective palladium(O)-catalyzed cross-coupling reaction of 6-bromo-5,8-dimethoxy-4-[(trifluoromethanesulfonyl)oxy]quinoline with N-(tert-butoxycarbonyl)-2-(trimethylstannyl)aniline promoted by Cu(I) and a hetero-Diels-Alder reaction of a quinoline-5,8-dione with acrolein N,N-dimethylhydrazone.