2-甲氧基-1-硝基萘 | 4900-66-7

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-甲氧基-1-硝基萘
• 英文名称: 2-methoxy-1-nitronaphthalene
• CAS: 4900-66-7
• 化学式: C₁₁H₉NO₃
• mdl: MFCD00100119
• 分子量: 203.197
• InChiKey: XDNSKIDXVJNJFO-UHFFFAOYSA-N

物化性质

• 熔点：
  127-128 °C
• 沸点：
  357.7±17.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2909309090
• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319
• 储存条件：
  存储条件：2-8°C，干燥

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  1-硝基-2-萘酚	1-nitro-2-naphthol	550-60-7	C10H7NO3	189.17

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	5-nitro-6-methoxy-2-bromonaphthalene	123856-15-5	C11H8BrNO3	282.093
  1-硝基-2-萘酚	1-nitro-2-naphthol	550-60-7	C10H7NO3	189.17
  ——	2-methoxy-4-methyl-1-nitronaphthalene	72206-99-6	C12H11NO3	217.224
  ——	1-Nitro-2-methoxy-4-(2-phenylethyl)-naphthalen	69745-41-1	C19H17NO3	307.349
  2-甲氧基萘-1-胺	2-methoxynaphthylamine	2246-42-6	C11H11NO	173.214

反应信息

• 作为反应物：
  描述：

  2-甲氧基-1-硝基萘 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 二乙二醇二甲醚 、 乙酸乙酯 为溶剂， 130.0 ℃ 、413.69 kPa 条件下， 反应 48.0h， 生成 1-(2-methoxy-1-naphthyl)piperazine
  参考文献：
  名称：

  N-(phthalimidoalkyl) derivatives of serotonergic agents: a common interaction at 5-HT1A serotonin binding sites?

  摘要：

  Several classes of agents are known to bind at central 5-HT1A serotonin sites In order to challenge the hypothesis that these agents bind in a relatively similar manner (i.e., share common aryl and terminal amine sites), we prepared N-(phthalimidobutyl) derivatives of examples of several such agents. With regard to arylpiperazines, we had previously shown that introduction of this functionality at the terminal amine is tolerated by the receptor and normally results in a significant (greater than 10-fold) enhancement in affinity. The results of the present study show that this bulky functionality is also tolerated by the receptor when incorporated into examples of all other major classes of 5-HT1A agents (e.g., 2-aminotetralin, phenylalklamine, indolylalkylamine, and (aryloxy)alkylamine derivatives). The length of the alkyl chain that separates the terminal amine from the phthalimido group is of major importance, and a four-carbon chain appears optimal. Alteration of the length of this chain can have a significant influence on affinity; decreasing the chain length from four to three carbon atoms can reduce affinity by an order of magnitude, and further shortening can have an even more pronounced effect.

  DOI：

  10.1021/jm00128a039
• 作为产物：
  描述：

  2-萘甲醚 在 三甲基氯硅烷 、 copper(ll) sulfate pentahydrate 、 硝酸胍 作用下， 以 乙腈 为溶剂， 以32%的产率得到2-甲氧基-1-硝基萘
  参考文献：
  名称：

  硝酸胍对富电子芳烃的无酸铜催化亲电硝化反应

  摘要：

  报道了一种实用的铜催化富电子芳烃与三甲基氯硅烷和硝酸胍的硝化反应。在无酸、开瓶和操作简单的条件下，在环境温度下以中等至优异的产率 (32–99%) 生成各种硝化产物。

  DOI：

  10.1021/acs.joc.1c03020

文献信息

• MONNA, a Potent and Selective Blocker for Transmembrane Protein with Unknown Function 16/Anoctamin-1
  作者：Soo-Jin Oh、Seok Jin Hwang、Jonghoon Jung、Kuai Yu、Jeongyeon Kim、Jung Yoon Choi、H. Criss Hartzell、Eun Joo Roh、C. Justin Lee

  DOI：10.1124/mol.113.087502

  日期：2013.11

  Transmembrane protein with unknown function 16/anoctamin-1 (ANO1) is a protein widely expressed in mammalian tissues, and it has the properties of the classic calcium-activated chloride channel (CaCC). This protein has been implicated in numerous major physiological functions. However, the lack of effective and selective blockers has hindered a detailed study of the physiological functions of this channel. In this study, we have developed a potent and selective blocker for endogenous ANO1 in Xenopus laevis oocytes (xANO1) using a drug screening method we previously established ([Oh et al., 2008][1]). We have synthesized a number of anthranilic acid derivatives and have determined the correlation between biological activity and the nature and position of substituents in these derived compounds. A structure-activity relationship revealed novel chemical classes of xANO1 blockers. The derivatives contain a −NO2 group on position 5 of a naphthyl group-substituted anthranilic acid, and they fully blocked xANO1 chloride currents with an IC50 < 10 μ M. The most potent blocker, N -((4-methoxy)-2-naphthyl)-5-nitroanthranilic acid (MONNA), had an IC50 of 0.08 μ M for xANO1. Selectivity tests revealed that other chloride channels such as bestrophin-1, chloride channel protein 2, and cystic fibrosis transmembrane conductance regulator were not appreciably blocked by 10∼30 μ M MONNA. The potent and selective blockers for ANO1 identified here should permit pharmacological dissection of ANO1/CaCC function and serve as potential candidates for drug therapy of related diseases such as hypertension, cystic fibrosis, bronchitis, asthma, and hyperalgesia. [1]: #ref-12

  跨膜蛋白16/anoctamin-1（ANO1）是一种在哺乳动物组织中广泛表达的蛋白质，具有经典钙激活氯通道（CaCC）的特性。这种蛋白质已被认为涉及许多主要的生理功能。然而，缺乏有效且选择性的阻断剂阻碍了对该通道生理功能的详细研究。在本研究中，我们利用先前建立的药物筛选方法（Oh等，2008），开发了一种对非洲爪蟾卵母细胞中内源性ANO1（xANO1）具有强效和选择性的阻断剂。我们合成了许多邻氨基苯甲酸衍生物，并确定了这些衍生物中的生物活性与取代基性质和位置之间的关联。从结构-活性关系中发现了一系列新的xANO1阻断剂化学类别。这些衍生物在萘基取代的邻氨基苯甲酸的5位含有一个−NO2基团，能完全阻断xANO1氯电流，IC50 < 10 μM。最强效的阻断剂，N -((4-甲氧基)-2-萘基)-5-硝基邻氨基苯甲酸（MONNA），对xANO1的IC50为0.08 μM。选择性测试表明，其他氯通道如bestrophin-1、氯通道蛋白2和囊性纤维化跨膜传导调节因子在10～30 μM MONNA下未被明显阻断。本研究识别出的对ANO1具有强效和选择性的阻断剂应能允许对ANO1/CaCC功能进行药理学解析，并作为治疗高血压、囊性纤维化、支气管炎、哮喘和痛觉过敏等相关疾病的潜在药物候选。
• Boron-Promoted Ether Interchange Reaction: Synthesis of Alkyl Nitroaromatic Ethers from Methoxynitroarenes
  作者：Zhenwei Liu、Nannan Luan、Hongtao Lu、Apeng Liang、Jingya Li、Dapeng Zou、Yangjie Wu、Yusheng Wu

  DOI：10.1002/ejoc.201901779

  日期：2020.2.14

  for boron‐promoted ether interchange reaction of methoxynitroarenes is reported. A series of methoxynitroarenes and alcohols, including primary, secondary, as well as tertiary alcohols, reacted smoothly in moderate to good yields under the optimized reaction conditions. This protocol is an operationally simple and scalable strategy for the synthesis of alkyl nitroaromatic ethers.

  报道了第一个硼促进甲氧基硝基芳烃的醚交换反应的方案。在优化的反应条件下，一系列的甲氧基硝基芳烃和醇，包括伯醇，仲醇和叔醇，以中等至良好的收率平稳反应。该协议是用于烷基硝基芳族醚合成的操作简单且可扩展的策略。
• Transetherification of 2,4-dimethoxynitrobenzene by aromatic nucleophilic substitution
  作者：Jiho Song、Hae Ju Kang、Jung Wuk Lee、Michelle A. Wenas、Seung Hwarn Jeong、Taeho Lee、Kyungsoo Oh、Kyung Hoon Min

  DOI：10.1371/journal.pone.0183575

  日期：——

  In view of the few reports concerning aromatic nucleophilic substitution reactions featuring an alkoxy group as a leaving group, the aromatic nucleophilic substitution of 2,4-dimethoxynitrobenzene was investigated with a bulky t-butoxide nucleophile under microwave irradiation. The transetherification of 2,4-dimethoxynitrobenezene with sodium t-butoxide under specific conditions, namely for 20 min

  鉴于关于以烷氧基为离去基团的芳族亲核取代反应的报道很少，因此在微波辐射下用大体积的叔丁氧基亲核体研究了2,4-二甲氧基硝基苯的芳族亲核取代。2，4-二甲氧基硝基苯与叔丁醇钠在特定条件下（即在110°C下于10％的二甲氧基乙烷的甲苯溶液中）进行20分钟的醚化反应，制得所需的产物，产率为87％，具有排他的邻位选择性。筛选各种反应条件以获得最大产率。2，4-二甲氧基硝基苯被叔丁醇芳族亲核取代应在受控条件下进行，以避免形成副产物，这与二卤代活化苯不同。在形成的副产物中，
• Iodine(III)-Catalyzed Electrophilic Nitration of Phenols via Non-Brønsted Acidic NO₂⁺ Generation
  作者：Kevin A. Juárez-Ornelas、J. Oscar C. Jiménez-Halla、Terumasa Kato、César R. Solorio-Alvarado、Keiji Maruoka

  DOI：10.1021/acs.orglett.8b04141

  日期：2019.3.1

  The first catalytic procedure for the electrophilic nitration of phenols was developed using iodosylbenzene as an organocatalyst based on iodine(III) and aluminum nitrate as a nitro group source. This atom-economic protocol occurs under mild, non-Brønsted acidic and open-flask reaction conditions with a broad functional-group tolerance including several heterocycles. Density functional theory (DFT)

  使用碘基苯作为基于碘（III）和硝酸铝作为硝基基团来源的有机催化剂，开发了用于苯酚亲电硝化的第一个催化程序。该原子经济方案发生在温和的，非布朗斯台德酸性和开放式烧瓶反应条件下，具有宽泛的官能团耐受性，包括多个杂环。（SMD：MeCN）Mo8-HX /（LANLo8 + f，6-311 + G *）水平的密度泛函理论（DFT）计算表明反应通过阳离子途径进行，该途径有效地产生了NO 2 +离子，从而是中性条件下的硝化物种。
• [EN] ION CHANNEL ANTAGONISTS/BLOCKERS AND USES THEREOF<br/>[FR] ANTAGONISTES/BLOQUEURS DES CANAUX IONIQUES ET LEURS UTILISATIONS
  申请人：SHANGHAI EAST HOSPITAL

  公开号：WO2021114313A1

  公开（公告）日：2021-06-17

  Provided are ion channel antagonists/blockers and uses thereof. Specifically, it provides the compounds of formula (I) or pharmaceutically acceptable salts, stereoisomers, solvates or prodrugs, preparation method therefor and application thereof. Definition of each group in the formula can be found in the specification for details. Provided is also pharmaceutical composition useful for treatment of heart disease and other ion channel related diseases.

  提供了离子通道拮抗剂/阻断剂及其用途。具体而言，提供了式（I）的化合物或药用盐、立体异构体、溶剂合物或前药，其制备方法及应用。每个式中的各个基团的定义可在说明书中找到详细信息。还提供了用于治疗心脏病和其他离子通道相关疾病的药物组合物。