2-nitro-1-methoxynaphthalene | 4900-62-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-nitro-1-methoxynaphthalene
• 英文别名: 1-Methoxy-2-nitronaphthalene；methyl-(2-nitro-[1]naphthyl)-ether；Methyl-(2-nitro-[1]naphthyl)-aether；2-Nitro-1-methoxy-naphthalin
• CAS: 4900-62-3
• 化学式: C₁₁H₉NO₃
• 分子量: 203.197
• InChiKey: MADSSDZXBDQMAF-UHFFFAOYSA-N

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

反应信息

• 作为反应物：
  描述：

  2-nitro-1-methoxynaphthalene 在 三氯化铁 、 甲烷 、 一水合肼 、 magnesium 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 11.0h， 生成 [1,1'-binaphthalen]-2-amine
  参考文献：
  名称：

  Nucleophilic aromatic substitution on 1-alkoxy-2-nitronaphthalene by 1-naphthyl Grignard reagents for the synthesis of 2-nitro-1,1′-binaphthyls

  摘要：

  Treatment of 1-methoxy-2-nitronaphthalene with 1-naphthyl- and 2-methoxy-1-naphthylmagnesium bromide in diethyl ether-benzene at room temperature provides a facile entry to the corresponding 2-nitro-1, 1'-binaphthyls in high yields. Induction of axial chirality into the binaphthyl bond has been achieved by using 1-menthoxy-2-nitronaphthalene as the substrate, giving 2-methoxy-2'-nitro-1, 1'-binaphthyl of 78% ee. Also reported is the optical resolution of 2-amino-1,1'-binaphthyls, which can be easily prepared by reduction of the 2-nitro-1,1'-binaphthyls, by preparative LC on a cellulose-derived chiral stationary phase, or on silica gel after conversion into the diastereomeric menthyl carbamates. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01143-7
• 作为产物：
  描述：

  1-甲氧基萘 在 亚硝酸特丁酯 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以14%的产率得到2-nitro-1-methoxynaphthalene
  参考文献：
  名称：

  一种富电子芳烃的直接硝化方法

  摘要：

  本发明公开了一种富电子芳烃的直接硝化合成方法，属于有机合成领域。本发明提供一种新型绿色自由基硝化方法，以芳烃为原料，与绿色硝化试剂叔丁基亚硝酸酯(TBN)在室温条件下，以乙腈、二氯甲烷、氯仿或丙酮作为反应溶剂，发生自由基硝化反应，获得硝基芳烃。本发明不使用金属参与反应，利用亚硝酸叔丁酯直接参与硝化反应。本发明引入供电子基如OMe，提高芳香化合物的电子密度，增加硝化反应的可能性。本发明减少亚硝酸叔丁酯的使用量。本发明反应只生成产物和叔丁醇，减少了环境污染。本发明方法在硝基芳烃合成领域具有重要的应用前景，真正意义上实现了绿色硝化，也为大规模工业化生产硝基芳烃提供了一条新的思路。

  公开号：

  CN108530242A

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。
• Improved Nitrations Using Metal Nitrate–Sulfuric Acid Systems
  作者：John M. Mellor、Stifun Mittoo、Rachel Parkes、Ross W. Millar

  DOI：10.1016/s0040-4020(00)00720-1

  日期：2000.9

  and di-nitration of aromatic substrates have been developed using ceric ammonium nitrate suspended in dichloromethane in the presence of 2 equiv. of sulfuric acid. By suspending the sulfuric acid on silica gel following nitration, products are easily isolated by filtration and evaporation of solvent. In these nitrations ceric ammonium nitrate can be replaced by other metal nitrates, for example potassium-

  已经开发了在2当量存在下使用悬浮在二氯甲烷中的硝酸铈硝酸铵对芳香族底物进行有效的单硝化和双硝化的方法。硫酸。硝化后，通过将硫酸悬浮在硅胶上，可以通过过滤和蒸发溶剂轻松分离出产物。在这些硝化反应中，硝酸铈铵可以被其他金属硝酸盐，例如硝酸钾或四丁基硝酸铵代替。相反，在甲醇和硫酸的存在下，硝酸铈铵对萘的硝化反应提供了1,4-和1,2-甲氧基硝基萘的混合物，但是使用硝酸钾或四丁基铵不能实现这些硝化反应。讨论了这种硝化/氧化的机理。
• [EN] TOLL-LIKE RECEPTOR AGONISTS<br/>[FR] AGONISTES DE RÉCEPTEURS DE TYPE TOLL
  申请人：UNIV KANSAS

  公开号：WO2015023958A1

  公开（公告）日：2015-02-19

  Compounds described herein can be used for therapeutic purposes. The compounds can be TLR agonists, such as TLR7 or TLR8 agonists. The compounds can be included in pharmaceutical compositions and used for therapies were being a TLR agonist is useful. The pharmaceutical compositions can include any ingredients, such as carries, diluents, excipients, fillers or the like that are common in pharmaceutical compositions. The compounds can be those illustrated or described herein as well as derivatives thereof, prodrugs thereof, salts thereof, or stereoisomers thereof, or having any chirality at any chiral center, or tautomer, polymorph, solvate, or combinations thereof. As such, the compounds can be used as adjuvants in vaccines, as well as for other therapeutic purposes described herein.

  本文描述的化合物可用于治疗目的。这些化合物可以是TLR激动剂，例如TLR7或TLR8激动剂。这些化合物可以包含在药物组合物中，并用于需要作为TLR激动剂有用的治疗中。药物组合物可以包括任何成分，如载体、稀释剂、赋形剂、填料或类似的在药物组合物中常见的成分。这些化合物可以是本文所示或描述的化合物，以及其衍生物、前药、盐、立体异构体，或在任何手性中心具有任何手性，或互变异构体、多晶形、溶剂化合物，或其组合。因此，这些化合物可以用作疫苗的佐剂，以及用于本文描述的其他治疗目的。
• Regioselective Functionalization of 9,9-Dimethyl-9-silafluorenes by Borylation, Bromination, and Nitration
  作者：Masahito Murai、Naoki Nishinaka、Mizuki Kimura、Kazuhiko Takai

  DOI：10.1021/acs.joc.9b00598

  日期：2019.5.3

  Despite the utility of 9-silafluorenes as functional materials and as building blocks, methods for efficient functionalization of their backbone are rare, probably because of the presence of easily cleavable C–Si bonds. Although controlling the regioselectivity of iridium-catalyzed direct borylation of C–H bonds is difficult, we found that bromination and nitration of 2-methoxy-9-silafluorene under

  尽管使用9硅芴作为功能材料和结构单元，但对其骨架进行有效功能化的方法却很少，这可能是由于存在易于裂解的C-Si键所致。尽管很难控制铱催化的C–H键直接硼化的区域选择性，但我们发现2-甲氧基-9-硅芴在温和条件下的溴化和硝化主要发生在富电子位置。具有甲氧基和溴基的所得产物可用作合成不对称取代的含9-硅芴的π-共轭分子的结构单元。
• Preparation of fluoronitronaphthalenes via a modified Schiemann reaction
  作者：Earl Brill

  DOI：10.1039/j39660000748

  日期：——

  1-Fluoro-2-nitro-, and 2-fluoro-1-nitro-naphthalene were prepared in 10–15% yields by the diazotisation of the corresponding nitroamine fluoborate salts in tetrahydrofuran, followed by decomposition of the diazonium fluoborate salts. This is the first reported synthesis of 1-fluoro-2-nitronaphthalene.

  通过将相应的硝基胺氟硼酸盐在四氢呋喃中重氮化，然后分解氟硼酸重氮盐，可以10-15％的收率制备1-氟-2-硝基萘和2-氟-1-硝基萘。这是首次报道的1-氟-2-硝基萘的合成。