2-((3-phenylprop-2-yn-1-yl)amino)naphthalene-1,4-dione | 1228797-85-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-((3-phenylprop-2-yn-1-yl)amino)naphthalene-1,4-dione
• 英文别名: 2-(3-phenyl-2-propynylamino)-1,4-naphthoquinone；2-(3-Phenylprop-2-ynylamino)naphthalene-1,4-dione；2-(3-phenylprop-2-ynylamino)naphthalene-1,4-dione
• CAS: 1228797-85-0
• 化学式: C₁₉H₁₃NO₂
• 分子量: 287.318
• InChiKey: BEBJBQQKJDMSRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 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：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-((3-phenylprop-2-yn-1-yl)amino)naphthalene-1,4-dione 在 copper dichloride 作用下， 以 硝基甲烷 为溶剂， 反应 4.0h， 以83%的产率得到3-chloro-4-phenylbenzo[g]quinoline-5,10-dione
  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
• 作为产物：
  描述：

  3-苯基-2-丙炔-1-胺 、 1,4-萘醌 在 sodium tetrachloroaurate(III) dihyrate 、 氧气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以60%的产率得到2-((3-phenylprop-2-yn-1-yl)amino)naphthalene-1,4-dione
  参考文献：
  名称：

  Azaanthraquinone assembly from N-propargylamino quinone via iodine-induced 6-endo-dig electrophilic cyclization

  摘要：

  通过碘诱导的 6-endo-dig 亲电环化，开发了一种利用氨基醌优异的亲核性来组装氮杂蒽醌框架的有效方法。因此，从N-炔丙基氨基醌出发，得到了各种3-碘-1-氮杂蒽醌，产率在45%至90%之间。无金属协议的特点是在氮杂蒽醌环上易于安装碘原子以及良好的官能团兼容性。

  DOI：

  10.1039/c004896h

文献信息

• Azaanthraquinone Assembly from <i>N</i>-Propargylamino Quinone via a Au(I)-Catalyzed 6-<i>endo</i>-<i>dig</i> Cycloisomerization
  作者：Chunhui Jiang、Min Xu、Shaozhong Wang、Huaqin Wang、Zhu-Jun Yao

  DOI：10.1021/jo1006637

  日期：2010.6.18

  the azaanthraquinone skeleton from N-propargylamino quinone by a Au(I)-catalyzed 6-endo-dig cycloisomerization was developed. The catalytic process was applied to the synthesis of alkaloid cleistopholine and its analogues. A mechanism involving benign nucleophilicity of the aminoquinone was proposed.

  开发了一种通过Au（I）催化的6- endo - dig环异构化从N-炔丙基氨基醌组装氮杂蒽醌骨架的方法。该催化过程被应用于生物碱抗胆碱及其类似物的合成。提出了涉及氨基醌良性亲核性的机理。
• COMPOUNDS FOR THE TREATMENT OF NEUROLOGICAL OR MITOCHONDRIAL DISEASES
  申请人：Musc Foundation for Research Development

  公开号：EP3829560A1

  公开（公告）日：2021-06-09
• [EN] COMPOUNDS FOR THE TREATMENT OF NEUROLOGICAL OR MITOCHONDRIAL DISEASES<br/>[FR] COMPOSÉS POUR LE TRAITEMENT DE MALADIES NEUROLOGIQUES OU MITOCHONDRIALES
  申请人：MUSC FOUND FOR RES DEV

  公开号：WO2020028222A1

  公开（公告）日：2020-02-06

  Compounds and methods are provided for the treatment of neurological or mitochondrial diseases, including epilepsy. In some embodiments, the compounds are substituted 1,4- naphthoquinones.
• CuCl₂-Promoted 6-<i>endo-dig</i> Chlorocyclization and Oxidative Aromatization Cascade: Efficient Construction of 1-Azaanthraquinones from <i>N</i>-Propargylaminoquinones
  作者：Na Fei、Hao Yin、Shaozhong Wang、Huaqin Wang、Zhu-Jun Yao

  DOI：10.1021/ol201542h

  日期：2011.8.19

  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.
• Azaanthraquinone assembly from N-propargylamino quinone via iodine-induced 6-endo-dig electrophilic cyclization
  作者：Na Fei、Qiwen Hou、Shaozhong Wang、Huaqin Wang、Zhu-Jun Yao

  DOI：10.1039/c004896h

  日期：——

  An efficient methodology taking advantage of the excellent nucleophilicity of aminoquinone to assemble the azaanthraquinone framework was developed via an iodine-induced 6-endo-dig electrophilic cyclization. Therefore, starting from N-propargylaminoquinones, various 3-iodo-1-azaanthraquinones were obtained in yields ranging from 45% to 90%. The metal-free protocol features facile installation of an iodine atom on the azaanthraquinone ring and benign functional group compatibility.

  通过碘诱导的 6-endo-dig 亲电环化，开发了一种利用氨基醌优异的亲核性来组装氮杂蒽醌框架的有效方法。因此，从N-炔丙基氨基醌出发，得到了各种3-碘-1-氮杂蒽醌，产率在45%至90%之间。无金属协议的特点是在氮杂蒽醌环上易于安装碘原子以及良好的官能团兼容性。