5-hydroxy-2-(1-hydroxyethyl)-1-methyl-1H-benzo[ f ]-indole-4,9-dione | 1332494-64-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-hydroxy-2-(1-hydroxyethyl)-1-methyl-1H-benzo[ f ]-indole-4,9-dione
• 英文别名: 5-hydroxy-2-(1-hydroxyethyl)-1-methyl-1H-benzo[ f ]indole-4,9-dione；5-hydroxy-2-(1-hydroxyethyl)-1-methyl-1H-benzo[f]indole-4,9-dione；5-hydroxy-2-(1-hydroethyl)-1-methyl-1H-benzo[f]indole-4,9-dione；1-methyl-2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]pyrrole-4,9-dione；5-Hydroxy-2-(1-hydroxyethyl)-1-methylbenzo[f]indole-4,9-dione
• CAS: 1332494-64-0
• 化学式: C₁₅H₁₃NO₄
• 分子量: 271.273
• InChiKey: CEDJZACYNFUTAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  79.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(dimethylamino)-5-hydroxynaphthalene-1,4-dione 在 copper(I) oxide 、 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 三乙胺 作用下， 以 吡啶 、 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 5-hydroxy-2-(1-hydroxyethyl)-1-methyl-1H-benzo[ f ]-indole-4,9-dione
  参考文献：
  名称：

  Concise Synthesis of Heterocycle-Fused Naphthoquinones by Employing Sonogashira Coupling and Tandem Addition-Elimination/Intramolecular Cyclization

  摘要：

  开发了一种合成杂环融合萘醌类化合物（如萘并[2,3-b]-呋喃-4,9-二酮、1H-苯并[f]吲哚-4,9-二酮和萘并[2,3-b]噻吩-4,9-二酮）的简便方法。该方法采用了 Sonogashira 偶联和串联加成-消除/分子内环化技术，能够用一种底物制备多功能杂环融合萘醌。

  DOI：

  10.1248/cpb.c13-00102

文献信息

• NOVEL PREPARATION OF ANTICANCER-ACTIVE TRICYCLIC COMPOUNDS VIA ALKYNE COUPLING REACTION
  申请人：IIDA Akira

  公开号：US20120077986A1

  公开（公告）日：2012-03-29

  The present invention is directed to provide a novel preparation of anticancer-active tricyclic compounds via alkyne coupling reaction. The present invention provides a process for preparing a compound of formula (Ia) or (Ib): wherein R 1 is optionally substituted C 1-6 alkyl, etc.; W is O, S or NR 2 ; R 2 is hydrogen atom, etc., which comprises Step (a) in which a compound of formula (II): wherein R 1 is the same as defined above, and a compound of formula (III) or (IV): wherein R 2 is the same as defined above; R 3 is hydrogen atom, etc.; X is halogen atom, etc., are reacted in the presence of a base, a copper catalyst and a palladium catalyst in an aprotic polar solvent.

  本发明旨在通过炔烃偶联反应提供一种新型抗癌活性三环化合物的制备方法。本发明提供了一种制备式(Ia)或(Ib)的化合物的方法：其中R1为可选择的取代的C1-6烷基等；W为O、S或NR2；R2为氢原子等；其中包括步骤(a)，其中式(II)的化合物：其中R1与上述定义相同，和式(III)或(IV)的化合物：其中R2与上述定义相同；R3为氢原子等；X为卤原子等，在无水极性溶剂中，在碱、铜催化剂和钯催化剂的存在下反应。
• 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.
• Preparation of anticancer-active tricyclic compounds via alkyne coupling reaction
  申请人：Taheebo Japan Co., Ltd.

  公开号：EP2436669B1

  公开（公告）日：2016-01-13
• US8703979B2
  申请人：——

  公开号：US8703979B2

  公开（公告）日：2014-04-22