3-甲氧基-4-(对硝基苄氧基)苯甲醛 | 81307-09-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-甲氧基-4-(对硝基苄氧基)苯甲醛
• 中文别名: 3-甲氧基-4-(4-硝基-苄氧基)-苯甲醛
• 英文名称: 3-methoxy-4-((4-nitrobenzyl)oxy)benzaldehyde
• 英文别名: 3-Methoxy-4-[(4-nitrophenyl)methoxy]benzaldehyde
• CAS: 81307-09-7
• 化学式: C₁₅H₁₃NO₅
• mdl: MFCD00016711
• 分子量: 287.272
• InChiKey: LBZHTZHIZXKRQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2913000090

反应信息

• 作为反应物：
  描述：

  3-甲氧基-4-(对硝基苄氧基)苯甲醛 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 4.0h， 以84%的产率得到香草醛
  参考文献：
  名称：

  Solid-Supported Acids for Debenzylation of Aryl Benzyl Ethers

  摘要：

  Solid-supported acids have been investigated for aromatic debenzylation reactions. Stoichiometric amounts of solid-supported acids in refluxing toluene with or without 4 equiv of methanol effectively provided the desired aromatic debenzylation products of various systems in moderate to excellent yields (up to 98%).

  DOI：

  10.1021/jo052337v
• 作为产物：
  描述：

  香草醛 、 对硝基溴化苄 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-甲氧基-4-(对硝基苄氧基)苯甲醛
  参考文献：
  名称：

  Synthesis, Characterization and Antimicrobial Activities of Organosilicon(IV) Complexes

  摘要：

  合成了香兰素和噻吩-2-羧酸酰肼的新型有机硅（IV）配合物，并通过元素分析、摩尔电导、红外线和核磁共振（1H、13C 和 29Si）光谱分析对其进行了表征。对合成的化合物进行了抗菌活性筛选，以检测其对革兰氏阳性菌（肺炎金葡菌和金黄色葡萄球菌）、革兰氏阴性菌（大肠杆菌和产气大肠杆菌）、真菌（黑木耳和白僵菌）的抗菌活性。研究发现，一些化合物的活性高于检测中使用的标准药物，与各自的游离配体相比，与硅原子配位的化合物的抗菌活性进一步提高。

  DOI：

  10.14233/ajchem.2018.21315

文献信息

• Scavenger assisted combinatorial process for preparing libaries of secondary amine compounds
  申请人：ELI LILLY AND COMPANY

  公开号：EP0818431A1

  公开（公告）日：1998-01-14

  This invention relates to a novel solution phase process for the preparation of secondary amine combinatorial libraries. These libraries have use for drug discovery and are used to form wellplate components of novel assay kits.

  这项发明涉及一种新颖的溶液相过程，用于制备次胺组合化合物库。这些库对药物发现具有用途，并用于形成新型测定试剂盒的孔板组分。
• Facile Synthesis of Novel Vanillin Derivatives Incorporating a Bis(2-hydroxyethyl)dithhioacetal Moiety as Antiviral Agents
  作者：Jian Zhang、Lei Zhao、Chun Zhu、Zengxue Wu、Guoping Zhang、Xiuhai Gan、Dengyue Liu、Jianke Pan、Deyu Hu、Baoan Song

  DOI：10.1021/acs.jafc.7b01035

  日期：2017.6.14

  A series of vanillin derivatives incorporating a bis(2-hydroxyethyl)dithioacetal moiety was designed and synthesized via a facile method. A plausible reaction pathway was proposed and verified by computational studies. Bioassay results demonstrated that target compounds possessed good to excellent activities against potato virus Y (PVY) and cucumber mosaic virus (CMV), of which, compound 6f incorporating

  通过简便的方法设计并合成了一系列结合有双（2-羟乙基）二硫缩醛部分的香兰素衍生物。提出了合理的反应途径，并通过计算研究进行了验证。生物测定结果表明，目标化合物具有抗马铃薯病毒Y（PVY）和黄瓜花叶病毒（CMV）的良好至优异的活性，其中化合物6f结合了双（2-羟乙基）二硫缩醛部分，在体内对PVY和CMV表现出最佳的治疗和保护活性，其50％有效浓度分别为217.6、205.7μg/ mL和206.3、186.2μg/ mL，优于利巴韦林（分别为848.0、808.1μg/ mL和858.2、766.5μg/ mL），杜布林（分别为462.6、454.8μg/ mL和471.2、465.4μg/ mL）和宁南霉素（440.5、425.3μg/ mL和426.1、405.3μg/ mL）。当前的研究为结合双（2-羟乙基）二硫缩醛作为新抗病毒剂的香兰素衍生物的应用提供了支持。
• Syntheses, spectroscopic and crystallographic characterizations of 4-nitrobenzyloxy derivatives and benzofurans from ortho-substituted benzaldehydes and 4-nitrobenzyl bromide
  作者：Zeliha Hayvali、Hakan Dal、Pinar Köksal、Duygu Şahin、Tuncer Hökelek

  DOI：10.1007/s11224-010-9618-6

  日期：2010.8

  A series of benzyloxybenzaldehyde derivatives (1–3) were prepared by the reactions of 4-nitrobenzyl bromide with 4-hydroxy-3-methoxybenzaldehyde (vanillin), 2-hydroxy-3-methoxybenzaldehyde (o-vanillin) and 2-hydroxy-4-methoxybenzaldehyde. When the reaction time is quite long, benzofuran derivatives (4 and 5) were obtained by the reactions of ortho-hydroxyaldehydes with the 4-nitrobenzyl bromide. Condensation reactions among the three benzyloxybenzaldehyde derivatives (1–3) with 2-aminomethylfuran (furfurylamine) yielded the new imine compounds (6–8). The structures of these aldehydes (1–3), benzofuran derivatives (4 and 5) and imine compounds (6–8) were confirmed on the basis of elemental analyses, IR, 1H NMR and 13C NMR and mass spectroscopy. The solid-state structures of compounds 4–6 were determined by single-crystal X-ray crystallography.

  通过 4-硝基溴化苄与 4-羟基-3-甲氧基苯甲醛（香兰素）、2-羟基-3-甲氧基苯甲醛（邻香兰素）和 2-羟基-4-甲氧基苯甲醛的反应，制备了一系列苄氧基苯甲醛衍生物（1-3）。当反应时间较长时，正羟基醛与 4-硝基溴化苄反应可得到苯并呋喃衍生物（4 和 5）。三种苄氧基苯甲醛衍生物（1-3）与 2-氨基甲基呋喃（糠胺）发生缩合反应，生成了新的亚胺化合物（6-8）。这些醛（1-3）、苯并呋喃衍生物（4 和 5）和亚胺化合物（6-8）的结构已通过元素分析、红外光谱、1H NMR 和 13C NMR 以及质谱得到确认。化合物 4-6 的固态结构是通过单晶 X 射线晶体学确定的。
• Scavenger assisted combinatorial process for preparing libraries of tertiary amine compounds
  申请人：ELI LILLY AND COMPANY

  公开号：EP0816310A2

  公开（公告）日：1998-01-07

  This invention relates to a novel solution phase process for the preparation of tertiary amine combinatorial libraries. These libraries have utility for drug discovery and are used to form wellplate components of novel assay kits.

  本发明涉及一种用于制备叔胺组合库的新型溶液相工艺。这些文库可用于药物发现，并可用于形成新型检测试剂盒的井板成分。
• Vanillin-derived antiproliferative compounds influence Plk1 activity
  作者：Roberto Carrasco-Gomez、Sarah Keppner-Witter、Martina Hieke、Lisa Lange、Gisbert Schneider、Manfred Schubert-Zsilavecz、Ewgenij Proschak、Birgit Spänkuch

  DOI：10.1016/j.bmcl.2014.09.015

  日期：2014.11

  We synthesized a series of vanillin-derived compounds and analyzed them in HeLa cells for their effects on the proliferation of cancer cells. The molecules are derivatives of the lead compound SBE13, a potent inhibitor of the inactive conformation of human polo-like kinase 1 (Plk1). Some of the new designs were able to inhibit cancer cell proliferation to a similar extent as the lead structure. Two of the compounds (((4-[(6-chloropyridin-3-yl)methoxy]-3-methoxyphenyl}methyl)(pyridin-4-ylmethyl)amine) and ((4-[(4-chlorophenyl)methoxy]-3-methoxyphenyl}methyl)(pyridin-4-ylmethyl)amine)) were much stronger in their capacity to reduce HeLa cell proliferation and turned out to potently induce apoptosis and reduce Plk1 kinase activity in vitro. (C) 2014 Published by Elsevier Ltd.