5-Amino-3-(4-hydroxy-3-nitrophenyl)-6-oxa-15,22-diazapentacyclo[12.8.0.02,7.08,13.016,21]docosa-1(22),2(7),4,8,10,12,14,16,18,20-decaene-4-carbonitrile | 1263278-25-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 5-Amino-3-(4-hydroxy-3-nitrophenyl)-6-oxa-15,22-diazapentacyclo[12.8.0.02,7.08,13.016,21]docosa-1(22),2(7),4,8,10,12,14,16,18,20-decaene-4-carbonitrile
• CAS: 1263278-25-6
• 化学式: C₂₆H₁₅N₅O₄
• 分子量: 461.436
• InChiKey: XDCHVUAPIYDKMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  35
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  151
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  邻苯二胺 在 copper(II) oxide 作用下， 反应 0.21h， 生成 5-Amino-3-(4-hydroxy-3-nitrophenyl)-6-oxa-15,22-diazapentacyclo[12.8.0.02,7.08,13.016,21]docosa-1(22),2(7),4,8,10,12,14,16,18,20-decaene-4-carbonitrile
  参考文献：
  名称：

  Nano copper(II) oxide catalyzed four-component synthesis of functionalized benzo[a]pyrano[2,3-c]phenazine derivatives

  摘要：

  简历 一项高效的一锅法定量制备功能化苯并[a]吡喃[2,3-c]吩嗪衍生物的方法已被开发，该方法通过2-羟基萘-1,4-二酮、邻苯二胺、醛和丙二腈的四组分反应，在纳米CuO催化剂存在下进行。铜(II)氧化物纳米颗粒可以回收并重复使用多次而不损失其活性。

  DOI：

  10.1016/j.crci.2012.09.012

文献信息

• An efficient four-component domino protocol for the rapid and green synthesis of functionalized benzo[a]pyrano[2,3-c]phenazine derivatives using caffeine as a homogeneous catalyst
  作者：Afshin Yazdani Elah Abadi、Malek-Taher Maghsoodlou、Reza Heydari、Razieh Mohebat

  DOI：10.1007/s11164-015-2083-5

  日期：2016.2

  A one-pot, two-step procedure has been used to synthesize functionalized benzo[a]pyrano[2,3-c]phenazine derivatives from a four-component condensation reaction of 2-hydroxynaphthalene-1,4-dione, o-phenylenediamine, aldehydes, and malononitrile in the presence of 1,3,7-trimethylpurine-2,6-dione (caffeine) as an expedient and reusable solid base catalyst. This new procedure has the following advantages: operational simplicity, short reaction times, environmentally friendly, easy work-up, and all the products were obtained in excellent yields.

  一种一步锅、两步法已被用于合成功能化的苯并[a]吡喃[2,3-c]菲啶衍生物，其方法为：在1,3,7-三甲基嘌呤-2,6-二酮（咖啡因）作为方便易回收的固体碱催化剂存在下，通过2-羟基萘-1,4-二酮、邻苯二胺、醛和丙二腈的四组分缩合反应。该新方法具有以下优点：操作简便、反应时间短、环境友好、易于处理，且所得产物均以优异的产率获得。
• Multicomponent Synthesis of Poly-Substituted Benzo[<i>a</i>]pyrano[2,3-<i>c</i>]phenazine Derivatives under Microwave Heating
  作者：Shu-Liang Wang、Fei-Yue Wu、Chuang Cheng、Ge Zhang、Yin-Ping Liu、Bo Jiang、Feng Shi、Shu-Jiang Tu

  DOI：10.1021/co1000376

  日期：2011.3.14

  one-pot two-step tandem synthesis of highly functionalized benzo[a]pyrano[2,3-c]phenazine derivatives via microwave-assisted multicomponent reactions of 2-hydroxynaphthalene-1,4-dione, diamines, aldehydes, and malononitrile is reported. The procedures are facile, avoiding time-consuming and costly syntheses, tedious workup, and purifications of precursors, as well as protection/deprotection of functional

  通过2-羟基萘-1,4-二酮，二胺，醛和丙二腈的微波辅助多组分反应，新的一锅两步串联合成高度官能化的苯并[a]吡喃并[2,3-c]吩嗪衍生物被报道。该过程是容易的，避免了费时且昂贵的合成，繁琐的后处理和前体的纯化以及对官能团的保护/脱保护。该方法有望在生物活性化合物的组合合成中找到应用，因​​为吩嗪和色烯基序具有广泛的生物活性。
• Theophylline as a new and green catalyst for the one-pot synthesis of spiro[benzo[ a ]pyrano[2,3- c ]phenazine] and benzo[ a ]pyrano[2,3- c ]phenazine derivatives under solvent-free conditions
  作者：Afshin Yazdani-Elah-Abadi、Malek-Taher Maghsoodlou、Razieh Mohebat、Reza Heydari

  DOI：10.1016/j.cclet.2016.09.016

  日期：2017.2

  A green, convenient, high yielding and one-pot procedure for the synthesis of novel spiro[benzo[a]pyrano[2,3-c]phenazine] derivatives by domino multi-component condensation reaction between 2-hydroxynaphthalene-1,4-dione, benzene-1,2-diamines, ninhydrine, and malononitrile in the presence of a catalytic amount of 1,3-dimethyl-7H-purine-2,6-dione (theophylline) as an expedient, eco-friendly and reusable

  通过2-羟基萘-1,4-之间多米诺骨牌多组分缩合反应合成新型螺[苯并[a]吡喃并[2,3-c]吩嗪]衍生物的绿色简便方法催化量的1,3-二甲基-7H-嘌呤-2,6-二酮（茶碱）的存在下，二酮，苯1,2-二胺，茚三酮和丙二腈作为一种方便，生态友好且可重复使用的固体碱催化剂在热，微波辐射和无溶剂条件下。该方法也已成功用于苯并[a]吡喃并[2,3-c]吩嗪的合成。
• Mild basic ionic liquid catalyzed four component synthesis of functionalized benzo[a]pyrano[2,3-c]phenazine derivatives
  作者：Hamid Reza Shaterian、Majid Mohammadnia

  DOI：10.1016/j.molliq.2012.11.006

  日期：2013.1

  An efficient, mild, and one-pot quantitative procedure for the preparation of functionalized benzo[a]pyrano[2,3-c] phenazine derivatives from four component reaction of 2-hydroxynaphthalene-1,4-dione, o-phenylenediamine, aldehydes, and malononitrile in the presence of basic ionic liquids such as 1-butyl-3-methylimidazolium hydroxide, 3-hydroxypropanaminium acetate, pyrrolidinium formate, pyrrolidinium acetate, 1,8-diazabicyclo[5.4.0]-undec-7-en-8-ium acetate, and piperidinium formate as the catalysts has been developed. The ionic liquid was stable during the reaction process and could also be reused several times with consistent activity. This procedure may be a practical alternative to the existing one reported procedure to meet the need of academe as well as industries. (C) 2012 Elsevier B.V. All rights reserved.