2-(3-hydroxybut-1-yn-1-yl)-3-(methylamino)naphthalene-1,4-dione | 1332494-65-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(3-hydroxybut-1-yn-1-yl)-3-(methylamino)naphthalene-1,4-dione
• 英文别名: 2-(3-Hydroxybut-1-ynyl)-3-(methylamino)naphthalene-1,4-dione；2-(3-hydroxybut-1-ynyl)-3-(methylamino)naphthalene-1,4-dione
• CAS: 1332494-65-1
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: MRFVBBQEBYEKNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-hydroxybut-1-yn-1-yl)-3-(methylamino)naphthalene-1,4-dione 在 吡啶 、 copper(I) oxide 、 palladium diacetate 、 3-丁炔-2-醇 、 copper(I) bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以45%的产率得到2-(1-hydroxyethyl)-1-methyl-1H-benzo[ f ]indole-4,9-dione
  参考文献：
  名称：

  Synthesis of indolequinones via a Sonogashira coupling/cyclization cascade reaction

  摘要：

  A mild strategy for constructing indolequinone motifs is described on the basis of the Sonogashira reaction and a copper-catalyzed intramolecular cyclization cascade reaction. The first step involves the palladium- and copper-catalyzed reaction between halogenated naphthoquinone and terminal acetylene to generate a coupling product, which then reacts in a copper-catalyzed intramolecular cyclization with the nitrogen functional group adjacent to the carbon-carbon triple bond. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.008
• 作为产物：
  描述：

  2-溴-3-(甲基氨基)-1,4-萘二酮 、 3-丁炔-2-醇 在 吡啶 、 copper(I) oxide 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以31%的产率得到2-(3-hydroxybut-1-yn-1-yl)-3-(methylamino)naphthalene-1,4-dione
  参考文献：
  名称：

  Synthesis of indolequinones via a Sonogashira coupling/cyclization cascade reaction

  摘要：

  A mild strategy for constructing indolequinone motifs is described on the basis of the Sonogashira reaction and a copper-catalyzed intramolecular cyclization cascade reaction. The first step involves the palladium- and copper-catalyzed reaction between halogenated naphthoquinone and terminal acetylene to generate a coupling product, which then reacts in a copper-catalyzed intramolecular cyclization with the nitrogen functional group adjacent to the carbon-carbon triple bond. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.008

文献信息

• One-Pot Synthesis of Benzo[f]indole-4,9-diones from 1,4-Naphthoquinones and Terminal Acetylenes
  作者：Mitsuaki Yamashita、Kazunori Ueda、Koichi Sakaguchi、Harukuni Tokuda、Akira Iida

  DOI：10.1248/cpb.59.1289

  日期：——

  In this paper, a concise one-pot method for the construction of benzo[f]indole-4,9-dione motifs is described. These transformations proceed via a sequential palladium- and copper-catalyzed coupling reaction of 1,4-naphthoquinones with terminal acetylenes, followed by a copper-catalyzed intramolecular cyclization reaction of the resulting coupling product.

  本文介绍了一种构建苯并[f]吲哚-4,9-二酮基团的简便的一锅法。这些转化是通过钯和铜催化的 1,4-萘醌与末端乙炔的连续偶联反应进行的，然后是铜催化的偶联产物的分子内环化反应。
• Synthesis of indolequinones via a Sonogashira coupling/cyclization cascade reaction
  作者：Mitsuaki Yamashita、Kazunori Ueda、Koichi Sakaguchi、Akira Iida

  DOI：10.1016/j.tetlet.2011.07.008

  日期：2011.9

  A mild strategy for constructing indolequinone motifs is described on the basis of the Sonogashira reaction and a copper-catalyzed intramolecular cyclization cascade reaction. The first step involves the palladium- and copper-catalyzed reaction between halogenated naphthoquinone and terminal acetylene to generate a coupling product, which then reacts in a copper-catalyzed intramolecular cyclization with the nitrogen functional group adjacent to the carbon-carbon triple bond. (C) 2011 Elsevier Ltd. All rights reserved.