isoascididemin | 133400-90-5

• 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: isoascididemin
• 英文别名: 8H-benzo[b]pyrido[4,3,2-de][1,10]phenanthrolin-8-one；3,10,20-Triazapentacyclo[11.7.1.02,7.09,21.014,19]henicosa-1(20),2(7),3,5,9,11,13(21),14,16,18-decaen-8-one
• CAS: 133400-90-5
• 化学式: C₁₈H₉N₃O
• 分子量: 283.289
• InChiKey: ZOEYUXZGLBXDAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-bromo-5,8-dimethoxy-4-<(trifluoromethanesulfonyl)-oxy>quinoline 在 盐酸 、 四(三苯基膦)钯 、 ammonium cerium(IV) nitrate 、 硫酸 、 三氟乙酸 、 lithium chloride 、 copper(I) bromide 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 79.75h， 生成 isoascididemin
  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：——
• Assembly of pentacyclic pyrido[4,3,2-mn]acridin-8-ones via a domino reaction initiated by Au(I)-catalyzed 6-endo-dig cycloisomerization of N-propargylaminoquinones
  作者：Hao Yin、Fanji Kong、Shaozhong Wang、Zhu-Jun Yao

  DOI：10.1016/j.tetlet.2012.10.065

  日期：2012.12

  A novel methodology taking advantage of a domino reaction initiated by an Au(I)-catalyzed 6-endo-dig cycloisomerization under silver-free condition was developed to prepare pentacyclic pyrido[4,3,2-mn]acridin-8-ones from N-propargylaminoquinones. Triphenylphosphinegold(I) chloride in combination with TFA was firstly employed and displayed excellent catalytic efficiency in the domino reaction. (C) 2012 Elsevier Ltd. All rights reserved.
• 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.