1,2-二甲氧基-4-(硝基甲基)苯 | 114131-33-8

• 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: 1,2-二甲氧基-4-(硝基甲基)苯
• 英文名称: (3,4-dimethoxyphenyl)nitromethane
• 英文别名: 1,2-dimethoxy-4-(nitromethyl)benzene
• CAS: 114131-33-8
• 化学式: C₉H₁₁NO₄
• 分子量: 197.191
• InChiKey: DHOHQWRMMYNZLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-二甲氧基-4-(硝基甲基)苯 在 potassium hydroxide 、 potassium permanganate 、 disodium hydrogenphosphate 、 水 、 盐酸 、 sodium thiosulfate 、 sodium chloride 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 0.17h， 以97%的产率得到藜芦酸
  参考文献：
  名称：

  KMnO₄-Mediated Oxidation as a Continuous Flow Process

  摘要：

  An efficient and easily scalable transformation of alcohols and aldehydes to carboxylic acids and nitroalkane derivatives to the corresponding carbonyls and carboxylic acids using permanganate as the oxidant within a continuous flow reactor is reported. Notably, the generation and downstream processing of MnO2 slurries was not found to cause any blocking of the reactor when ultrasound pulses were applied to the flow system.

  DOI：

  10.1021/ol101345z
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛肟 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以1.26 g的产率得到1,2-二甲氧基-4-(硝基甲基)苯
  参考文献：
  名称：

  Organocatalytic, Diastereo- and Enantioselective Synthesis of Nonsymmetric cis-Stilbene Diamines: A Platform for the Preparation of Single-Enantiomer cis-Imidazolines for Protein–Protein Inhibition

  摘要：

  The finding by scientists at Hoffmann-La Roche that cis-imidazolines could disrupt the protein-protein interaction between p53 and MDM2, thereby inducing apoptosis in cancer cells, raised considerable interest in this scaffold over the past decade. Initial routes to these small molecules (i.e., Nutlin-3) provided only the racemic form, with enantiomers being enriched by chromatographic separation using high-pressure liquid chromatography (HPLC) and a chiral stationary phase. Reported here is the first application of an enantioselective aza-Henry approach to nonsymmetric cis-stilbene diamines and cis-imidazolines. Two novel mono(amidine) organocatalysts (MAM) were discovered to provide high levels of enantioselection (>95% ee) across a broad range of substrate combinations. Furthermore, the versatility of the aza-Henry strategy for preparing nonsymmetric cis-imidazolines is illustrated by a comparison of the roles of aryl nitromethane and aryl aldimine in the key step, which revealed unique substrate electronic effects providing direction for aza-Henry substrate-catalyst matching. This method was used to prepare highly substituted cis-4,5-diaryl imidazolines that project unique aromatic rings, and these were evaluated for MDM2-p53 inhibition in a fluorescence polarization assay. The diversification of access to cis-stilbene diamine-derived imidazolines provided by this platform should streamline their further development as chemical tools for disrupting protein-protein interactions.

  DOI：

  10.1021/jo501003r

文献信息

• Intramolecular Biaryl Oxidative Coupling of Stilbenes by Vanadium Oxytrichloride (VOCl₃): Facile Synthesis of Substituted Phenanthrene Derivatives
  作者：Zhong Jin、Qingmin Wang、Runqiu Huang

  DOI：10.1081/scc-120027245

  日期：2004.12.31

  Abstract Vanadium oxytrichloride (VOCl3) has proven to be a highly efficient reagent for intramolecular biaryl oxidative coupling reaction of electron‐rich stilbenes. Accordingly, a mild and efficient route to phenanthrene derivatives from stilbenes oxygenated is developed.

  摘要 三氯氧化钒 (VOCl3) 已被证明是富电子二苯乙烯分子内联芳基氧化偶联反应的高效试剂。因此，开发了一种从二苯乙烯氧化得到菲衍生物的温和有效的途径。
• [EN] ARYL-SUBSTITUTED IMIDAZOLES AND METHODS OF MAKING AND USING SAME<br/>[FR] IMIDAZOLES SUBSTITUÉS PAR UN ARYL ET LEURS PROCÉDÉS DE PRÉPARATION ET D'UTILISATION
  申请人：ST JUDE CHILDRENS RES HOSPITAL

  公开号：WO2015184383A1

  公开（公告）日：2015-12-03

  The compounds of the invention are antagonists of MDM2 and/or MDMX, with excellent specificity for MDM2 and/or MDMX over other proteins. Several analogs demonstrate selective binding affinity to MDMX over MDM2. The disclosed compounds can therefore regulate p53 activity and treat a variety of cancers. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  该发明的化合物是MDM2和/或MDMX的拮抗剂，对MDM2和/或MDMX具有极好的特异性，优于其他蛋白质。几种类似物表现出对MDMX比对MDM2具有选择性结合亲和力。因此，所披露的化合物可以调节p53活性并治疗多种癌症。本摘要旨在作为在特定领域进行搜索的扫描工具，并不打算限制本发明。
• A New and Convenient Method for the Synthesis of Dehydroamino Acids Starting from Ethyl<b><i>N</i></b>-Boc- and<b><i>N</i></b>-<b><i>Z</i></b>-<b><i>α</i></b>-Tosylglycinates and Various Nitro Compounds
  作者：Tanemasa Nagano、Hideki Kinoshita

  DOI：10.1246/bcsj.73.1605

  日期：2000.7

  Ethyl N-Boc- and N-Z-α-tosylglycinates, which were readily available from t-butyl or benzyl carbamate, ethyl glyoxylate, and sodium p-toluenesulfinate in formic acid, were reacted with a variety of nitro compounds in the presence of a base to afford the corresponding α,β-didehydroamino acid derivatives in good yields. Eventually, it was found that the (Z)-isomer was predominantly formed in the present

  N-Boc- 和 NZ-α-甲苯磺酰基甘氨酸乙酯很容易从甲酸中的氨基甲酸叔丁酯或苄酯、乙醛酸乙酯和对甲苯亚磺酸钠中获得，在碱存在下与各种硝基化合物反应以良好的收率提供相应的α,β-二脱氢氨基酸衍生物。最终，发现在本方法中主要形成(Z)-异构体。
• Preparation of Ring-Methoxylated Arylnitromethanes by the Victor Meyer Reaction
  作者：Victor P. Kislyi、Anna S. Maksimenko、Petr A. Buikin、Elena D. Daeva、Victor V. Semenov

  DOI：10.1055/s-0041-1737534

  日期：2022.6

  arylnitromethanes and nitrite esters. A modified approach for the isolation of arylnitromethanes is described, which represents a valuable improvement of the established Victor Meyer reaction. The isolation technique, which involves reaction of the nitrite ester with urea in methanol, allows the desired arylnitromethanes to be isolated, without loss, in 29–75% yields, and generates the corresponding recyclable

  易于获得且稳定的环甲氧基化苄基氯与 AgNO2 反应生成相应的芳基硝基甲烷和亚硝酸酯的混合物。描述了一种改进的芳基硝基甲烷分离方法，它代表了对已建立的 Victor Meyer 反应的有价值的改进。该分离技术涉及亚硝酸酯与脲在甲醇中的反应，可以以 29-75% 的收率无损失地分离出所需的芳基硝基甲烷，并生成相应的可回收苯甲醇。出乎意料的是，环甲氧基化苄基碘不能使用，因为它们不够稳定并且在开发的反应条件下会产生焦油。
• Polyalkoxy-substituted nitrostilbenes in the synthesis of lamellarin analogs. Formal synthesis of lamellarin H
  作者：E. A. Silyanova、A. S. Maksimenko、M. D. Brunner、I. A. Koblov、V. P. Kislyi、A. V. Samet、V. V. Semenov

  DOI：10.1007/s11172-023-4003-y

  日期：2023.9

  Lamellarin D trimethyl ether was prepared by 1,3-dipolar cycloaddition of 6,7-dimethoxyisoquinolinium ylide to pentamethoxy-substituted nitrostilbene followed by a lactone ring closure in the intermediate cycloadduct. This approach allowed a formal synthesis of lamellarin H.

  通过 6,7-二甲氧基异喹啉鎓叶立德与五甲氧基取代的硝基茋进行 1,3-偶极环加成，然后在中间体环加合物中进行内酯环闭合，制备层片素 D 三甲醚。这种方法使得板层蛋白 H 得以正式合成。