3-amino-1-(3-methoxyl-4-methoxyl-5-methoxylphenyl)-1H-benzo[a]pyrano[2,3 c]phenazine-2-carbonitrile | 1263278-27-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 3-amino-1-(3-methoxyl-4-methoxyl-5-methoxylphenyl)-1H-benzo[a]pyrano[2,3 c]phenazine-2-carbonitrile
• 英文别名: 5-Amino-3-(3,4,5-trimethoxyphenyl)-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: 1263278-27-8
• 化学式: C₂₉H₂₂N₄O₄
• 分子量: 490.518
• InChiKey: PGUKUBGLAQHVGE-UHFFFAOYSA-N

物化性质

• 熔点：
  252-254 °C
• 沸点：
  743.4±60.0 °C(predicted)
• 密度：
  1.42±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  邻苯二胺 在 咖啡因 作用下， 以 neat (no solvent) 为溶剂， 反应 0.28h， 生成 3-amino-1-(3-methoxyl-4-methoxyl-5-methoxylphenyl)-1H-benzo[a]pyrano[2,3 c]phenazine-2-carbonitrile
  参考文献：
  名称：

  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

  摘要：

  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。

  DOI：

  10.1007/s11164-015-2083-5

文献信息

• Nano copper(II) oxide catalyzed four-component synthesis of functionalized benzo[a]pyrano[2,3-c]phenazine derivatives
  作者：Hamid Reza Shaterian、Farzaneh Moradi、Majid Mohammadnia

  DOI：10.1016/j.crci.2012.09.012

  日期：2012.11

  Résumé An efficient 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 nano CuO as the catalyst has been developed. The copper(II) oxide nanoparticles can be recovered and reused several times without loss of its activity.

  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。
• 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。
• Synthesis of benzopyranophenazine derivatives in the presence of Glycerol: Urea: NH4Cl mixture
  作者：Letcy V. Theresa、K. Sreekumar

  DOI：10.1016/j.molstruc.2022.134635

  日期：2023.3

  Deep eutectic solvents have become attractive alternatives to conventional solvents due to their interesting characteristics such as physicochemical properties, low cost of components, easiness to prepare, low toxicity, bio renewability and biodegradability. To make the deep eutectic mixture more cost effective and renewable, carbohydrate was linked with the deep eutectic mixture, since, carbohydrates

  低共熔溶剂由于其物理化学性质、成分成本低、易于制备、低毒性、生物可再生性和生物降解性等有趣特性，已成为传统溶剂的有吸引力的替代品。为了使低共熔混合物更具成本效益和可再生性，将碳水化合物与低共熔混合物联系起来，因为碳水化合物是最重要的可再生化合物。在这项工作中，我们使用由碳水化合物组成的低熔点混合物来创建用于有机转化的反应介质。研究了混合物的密度、粘度、酸度、折射率、表面张力、溶解度、玻璃化转变温度和热稳定性等物理性质。甘油：尿素：NH 4采用 Cl 低熔点混合物作为反应介质和催化剂，有效合成了苯并吡喃吩嗪甲腈，使反应成本低、安全并减少了有机溶剂的使用。邻苯二胺、2-羟基-1,4 萘醌、丙二腈和醛之间的反应有效进行，产率从好到极好。
• [(EtO)3Si(CH2)3N+H3][CH3COO−] as Basic Ionic Liquid Catalyst Promoted Green Synthesis of Benzo[a]pyrano[2,3-c]phenazine Derivatives in Homogenous Solution
  作者：Farhad Shirzaei、Hamid Reza Shaterian

  DOI：10.1007/s10953-023-01332-w

  日期：2024.2

  3-c]phenazine derivatives from four-component condensation reaction of 2-hydroxynaphthalene-1,4-dione, benzene-1,2-diamine, aromatic aldehydes, and malononitrile in the presence of [(EtO)3Si(CH2)3N+H3][CH3COO−] as basic ionic liquid as catalyst in homogenous solution under solvent-free conditions at 90 °C is described. Simple procedure, high yields, short reaction times, and an environmentally benign method are

  一种高效的一锅定量方法，用于从 2-羟基萘-1,4-二酮、苯-1,2-二胺的四组分缩合反应制备苯并[ a ]吡喃并[2,3-c]吩嗪衍生物、芳香醛和丙二腈，在[(EtO) 3 Si(CH 2 ) 3 N + H 3 ][CH 3 COO - ]作为碱性离子液体作为催化剂的存在下，在无溶剂条件下于90 °C下在均匀溶液中被描述。该方案具有程序简单、产率高、反应时间短和环境友好的优点。[(EtO) 3 Si(CH 2 ) 3 N + H 3 ][CH 3 COO - ]可以回收并重复使用多次而不损失其活性。
• 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.