2-[[3-(2-aminophenyl)prop-2-yn-1-yl]amino]-1,4-naphthalenedione | 1315369-86-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[[3-(2-aminophenyl)prop-2-yn-1-yl]amino]-1,4-naphthalenedione
• 英文别名: 2-[3-(2-aminophenyl)-2-propynylamino]-1,4-naphthoquinone；2-[3-(2-Aminophenyl)prop-2-ynylamino]naphthalene-1,4-dione
• CAS: 1315369-86-8
• 化学式: C₁₉H₁₄N₂O₂
• 分子量: 302.332
• InChiKey: WVBAZXUJEBBPLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  72.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[[3-(2-aminophenyl)prop-2-yn-1-yl]amino]-1,4-naphthalenedione 在 copper dichloride 作用下， 以 硝基甲烷 为溶剂， 反应 4.0h， 以48%的产率得到5-chloro-8H-benzo[c]pyrido[4,3,2-mn]acridin-8-one
  参考文献：
  名称：

  CuCl₂-Promoted 6-endo-dig Chlorocyclization and Oxidative Aromatization Cascade: Efficient Construction of 1-Azaanthraquinones from N-Propargylaminoquinones

  摘要：

  An efficient synthetic methodology was developed to assemble 1-azaanthraquinones from N-propargylaminoquinones by copper(II)-promoted sequential 6-endo-dig chlorocyclization and oxidative aromatization. The approach can be extended to preprare chlorinated alkaloids such as cleistophine and sampangine. A possible mechanism involving carbon-carbon bond formation triggered by regioselective electrophilic activation and carbon-chlorine bond formation via reductive elimination was proposed.

  DOI：

  10.1021/ol201542h

文献信息

• 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.