2,4,6-trimethoxy-β-nitrostyrene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,4,6-trimethoxy-β-nitrostyrene
• 英文别名: (E)-1,3,5-trimethoxy-2-(2-nitrovinyl)benzene；(E)-2,4,6-trimethoxy-β-nitrostyrene；(E)-2,4,6-Trimethoxy-β-nitro-styrol；2,4,6-Trimethoxy-beta-nitrostyrene；1,3,5-trimethoxy-2-[(E)-2-nitroethenyl]benzene
• 化学式: C₁₁H₁₃NO₅
• 分子量: 239.228
• InChiKey: URHPFHDNYKOMAI-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  73.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三乙基硼 、 2,4,6-trimethoxy-β-nitrostyrene 在 air 作用下， 以 正己烷 、 溶剂黄146 为溶剂， 生成 (E)-1,3,5-trimethoxy-2-(but-1-enyl)benzene
  参考文献：
  名称：

  One-pot synthesis of trans-β-alkylstyrenes

  摘要：

  One-pot synthesis of (E)-alkenes 5 from the reactions of aldehyde 1 and nitromethane 2 in the acetic acid solution and then with triethylborane 4 in the biphase of diethyl ether and aqueous Solution ill the presence of oxygen in air was reported. Various (E)-alkenes 7 could also be prepared when different kinds of secondary or tertiary alkyl iodides 6 were used under similar conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01185-6
• 作为产物：
  描述：

  硝基乙烷 、 1,3,5-三甲氧基苯 在 palladium(II) trifluoroacetate 、 silver(I) acetate 作用下， 以 乙二醇二甲醚 、 二甲基亚砜 为溶剂， 反应 24.0h， 以78%的产率得到2,4,6-trimethoxy-β-nitrostyrene
  参考文献：
  名称：

  Pd-Catalyzed Multidehydrogenative Cross-Coupling between (Hetero)Arenes and Nitroethane to Construct β-Aryl Nitroethylenes

  摘要：

  The Pd-catalyzed multidehydrogenative cross-coupling reactions of arenes with nitroethane are described. The established methods afford beta-aryl nitroethylenes that are an important class of synthetic Intermediates and biologically active compounds in an atom- and step-economical fashion. The reactions were applicable to substituted benzenes and a variety of heterocycles such as benzothiophenes, benzofurans, and indoles. Mechanistic experiments Indicated that beta-nitroethylbenzene might be the intermediate in this transformation.

  DOI：

  10.1021/ol400507u

文献信息

• The ultrasound promoted Knoevenagel condensation of aromatic aldehydes
  作者：James McNulty、Jennifer A. Steere、Sonja Wolf

  DOI：10.1016/s0040-4039(98)01789-4

  日期：1998.10

  Application of ultrasound has been found to greatly assist the Knoevenagel aldol condensation reaction of activated methylenes with aromatic aldehydes under mild conditions. The outcome of the ultrasound-promoted reaction depends upon the electronic nature of the armoatic aldehyde, the solvent employed and the addition of acids, bases or ammonium salts.

  已经发现，在温和的条件下，超声的应用极大地促进了活化的亚甲基与芳族醛的Knoevenagel醛醇缩合反应。超声促进反应的结果取决于电枢乙醛的电子性质，所用溶剂以及酸，碱或铵盐的添加。
• Investigation of pore-size effects on base catalysis using amino-functionalized monodispersed mesoporous silica spheres as a model catalyst
  作者：T SUZUKI、M YAMAMOTO、K FUKUMOTO、Y AKIMOTO、K YANO

  DOI：10.1016/j.jcat.2007.08.010

  日期：2007.10.25

  The effects of pore size on base catalysis have been studied using amino-functionalized monodispersed mesoporous silica spheres (NH2-MMSS). By changing the surfactant that is used for the template and also the synthetic conditions, NH2-MMSS with similar particle diameters (560–600 nm) and different pore sizes (0–2.66 nm) were successfully prepared. Because the NH2-MMSS that were obtained had the same

  使用氨基官能化的单分散介孔二氧化硅球（NH 2 -MMSS）研究了孔径对碱催化的影响。通过改变用于模板的表面活性剂以及合成条件，成功制备了具有相似粒径（560–600 nm）和不同孔径（0–2.66 nm）的NH 2 -MMSS。因为NH 2所获得的-MMSS具有相同的形状，粒径和中孔排列，催化活性的任何差异可基本上归因于其孔径的差异。我们将苯甲醛衍生物和硝基甲烷之间的硝基醛缩合反应作为碱催化反应。首次发现该反应主要在中孔内部进行（效率系数：0.63），并且通过改变反应物上取代基的类型和数量来影响NH 2 -MMSS的最佳孔径。另外，由于与其他类型的中孔二氧化硅相比，中孔的径向排列，发现NH 2 -MMSS是极好的催化剂。
• Pd-catalyzed cross-coupling of carboxylic acids with nitroethane via combination of decarboxylation and dehydrogenation
  作者：Min Zhang、Jun Zhou、Jian Kan、Min Wang、Weiping Su、Maochun Hong

  DOI：10.1039/c0cc01029d

  日期：——

  An unexpected coupling reaction of arene carboxylic acid with nitroethane via a combination of decarboxylation and dehydrogenation is described. The method provides exclusively (E)-beta-nitrostyrenes.

  描述了芳烃羧酸与硝基乙烷通过脱羧和脱氢的组合的意外偶联反应。该方法仅提供（E）-β-硝基苯乙烯。
• Multicomponent Cascade Reactions:  Sequential [1 + 4] and [2 + 3] Cycloadditions for the Generation of Heterocyclic Ring Systems
  作者：Nicolas M. Fédou、Philip J. Parsons、Eddy M. E. Viseux、Alan J. Whittle

  DOI：10.1021/ol050892d

  日期：2005.7.1

  [reaction: see text]. A novel intermolecular nitrile oxide cycloaddition sequence has been developed for the formation of highly substituted heterocyclic rings. Reaction of trimethylsilyl cyanide with epoxides generates isonitriles which can react with nitroalkenes to form N-(isoxazolylidene)alkylamines. After fragmentation to nitrile oxides, the dipoles can undergo intermolecular 1,3-dipolar cycloadditions

  [反应：请参见文字]。已经开发了用于形成高度取代的杂环的新型分子间一氧化氮环加成序列。三甲基甲硅烷基氰化物与环氧化物的反应生成异腈，该异腈可以与硝基烯烃反应形成N-（异恶唑基亚烷基）烷基胺。碎裂为一氧化氮后，偶极子可与电子缺陷型偶极亲电子发生分子间的1,3-偶极环加成反应，从而在一个合成操作中生成取代的异恶唑啉。
• CYTOKINE INHIBITORS
  申请人：Bandgar Babasaheb Pandurang

  公开号：US20130203815A1

  公开（公告）日：2013-08-08

  The present invention provides compounds represented by general formula (I): wherein, R 1 , R 2 , R 3 , L and T are as defined in the specification, in all their stereoisomeric and tautomeric forms and mixtures thereof in all ratios, and their pharmaceutically acceptable salts, pharmaceutically acceptable solvates, and prodrugs thereof. The invention also relates to processes for the manufacture of compounds of formula (I) and pharmaceutical compositions containing them. The compounds and the pharmaceutical compositions of the present invention are useful in the treatment of a condition or disorder mediated by one or more cytokines selected from Tumor Necrosis Factor-alpha (TNF-α) and interleukins such as IL-1, IL-6, and IL-8. The present invention further provides a method of treatment of inflammatory disorders by administering a therapeutically effective amount of the said compound of formula (I) or its pharmaceutical composition, to a mammal in need thereof.

  本发明提供了通式（I）所表示的化合物：其中，R1、R2、R3、L和T如规范中所定义，在其所有立体异构体和互变异构体形式及其在所有比例中的混合物中，以及其药学上可接受的盐、药学上可接受的溶剂化物和其前药。本发明还涉及制造通式（I）化合物和含有它们的制药组合物的过程。本发明的化合物和制药组合物在治疗由肿瘤坏死因子-α（TNF-α）和白细胞介素（如IL-1、IL-6和IL-8）中选择的一种或多种细胞因子介导的疾病或症状中有用。本发明还提供了一种通过向需要治疗的哺乳动物中给予所述通式（I）化合物或其制药组合物的治疗有效量来治疗炎症性疾病的方法。