4-硝基萘-1-腈 | 23245-63-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 4-硝基萘-1-腈
• 英文名称: 4-Nitronaphthalene-1-carbonitrile
• 英文别名: 1-cyano-4-nitronaphthalene；4-nitro-[1]naphthonitrile；4-Nitro-[1]naphthonitril；1-Nitro-4-cyanonaphthalin；1-Nitro-4-naphthonitril
• CAS: 23245-63-8
• 化学式: C₁₁H₆N₂O₂
• 分子量: 198.181
• InChiKey: SNUJXDIAMQLCNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-硝基萘-1-腈 在 barium dihydroxide 、 ammonium sulfide 作用下， 生成 1-萘胺
  参考文献：
  名称：

  Friedlaender; Weisberg, Chemische Berichte, 1895, vol. 28, p. 1839

  摘要：

  DOI：
• 作为产物：
  描述：

  1-氨基-4-硝基萘 生成 4-硝基萘-1-腈
  参考文献：
  名称：

  Friedlaender; Weisberg, Chemische Berichte, 1895, vol. 28, p. 1839

  摘要：

  DOI：

文献信息

• Dissociation of Naphthoic Acids in Non-Aqueous Media. Comparison of Benzene and Naphthalene Skeletons
  作者：Patrik Pařík、Jitka Wolfová、Miroslav Ludwig

  DOI：10.1135/cccc20000385

  日期：——

  Seven monosubstituted 1-naphthoic acids were synthesized by new or modified procedures, and their dissociation constants were measured potentiometrically at 25 °C in methanol, acetonitrile, dimethylformamide, and pyridine. Dissociation constants of these along with thirteen substituted 1-naphthoic acids and twenty-five substituted 2-naphthoic acids previously studied were measured at 25 °C in ethanol and dimethyl sulfoxide. The pK_HA values of 3- and 4-substituted 1-naphthoic acids were treated by simple linear regression and principal component analysis, and the results were used for comparison of model compounds and of corresponding 3- and 4-substituted benzoic acids with the aim of comparison of benzene and naphthalene skeletons. It has been found, the 3 and 4 positions of the 1-naphthyl system can roughly be compared with the meta and para positions of benzene, respectively.

  通过新的或修改过的程序合成了七种单取代的1-萘甲酸，并在25°C下在甲醇、乙腈、二甲基甲酰胺和吡啶中用电位法测量了它们的离解常数。这些单取代的1-萘甲酸与之前研究的十三种取代的1-萘甲酸和二十五种取代的2-萘甲酸的离解常数在25°C下在乙醇和二甲基亚砜中进行了测量。3-和4-取代的1-萘甲酸的pK_HA值通过简单线性回归和主成分分析进行处理，并将结果用于比较模型化合物以及目的是比较苯和萘骨架的相应3-和4-取代苯甲酸。研究发现，1-萘基系统的3位和4位可以分别与苯的间位和对位进行粗略比较。
• A novel application of the Diels–Alder reaction: nitronaphthalenes as normal electron demand dienophiles
  作者：Elisa Paredes、Romina Brasca、María Kneeteman、Pedro M.E. Mancini

  DOI：10.1016/j.tet.2007.02.054

  日期：2007.4

  detected as main product, suggesting that a competitive reaction would probably take place. The results clearly confirmed the dienophilic nature of nitronaphthalenic double bonds and provided an alternative procedure for phenanthrene derivatives and N-naphthylpyrroles' synthesis. The relative reactivity of the reactants and the viability of the reactions were discussed from a theoretical point of view.

  研究了硝基萘与丁二烯之间的热反应。结果表明，这些反应能够进行正常的电子需求Diels-Alder反应，并且各种二烯都能提供菲衍生物。还讨论了扩展名和取代类型的影响。当萘核的吸电子活化或二烯的供体性质不足时，检测到N-萘吡咯是主要产物，这表明可能发生竞争性反应。结果清楚地证实了硝基萘双键的双亲性质，并为菲衍生物和N提供了一种替代方法。-萘并吡咯的合成。从理论的角度讨论了反应物的相对反应性和反应的可行性。
• One-step synthesis of 2,9-disubstituted phenanthrenes via Diels–Alder reactions using 1,4-disubstituted naphthalenes as dienophiles
  作者：Elisa Paredes、Betina Biolatto、Marı́a Kneeteman、Pedro Mancini

  DOI：10.1016/s0040-4039(02)00879-1

  日期：2002.5

  electron-demand Diels–Alder reaction between 1,4-disubstituted naphthalenes, nitro being one of these two groups, and 1-methoxy-3-trimethylsililoxy-1,3-butadiene gives hydroxyphenanthrene derivatives, the yields being enhanced by placement of more electron-withdrawing groups on the dienophilic system. The nitro group as substituent directs the cycloaddition, and its cis-extrusion as nitrous acid along with the

  1,4-二取代的萘（硝基为这两个基团之一）与1-甲氧基-3-三甲基甲硅烷氧基-1,3-丁二烯之间的常规电子需求Diels-Alder反应可生成羟基菲衍生物，通过放置双亲系统上有更多的吸电子基团。作为取代基的硝基指导环加成，其作为亚硝酸的顺式挤出以及伯加合物中甲醇的损失导致预期的芳构化产物。
• Synthesis of Phenanthrenol Derivatives Through Polar Diels-Alder Reactions Employing Nitronaphthalenes and (E)-1-(Trimethylsilyloxy)-1,3- butadiene. Theoretical Calculations
  作者：María Kneeteman、Claudia Rosa、Carla Ormachea、Paula Giménez、Anna Baena、Pedro Mancini

  DOI：10.2174/1570178611666140123235852

  日期：2014.4

  The cycloaddition reactions between dinitronaphthalenes and (E)-1-trimethylsilyloxy-1,3-butadiene produce nitrophenanthrenol derivatives as principal products. The primary adducts suffer the irreversible lost of nitrous acid and, consequently, the aromatization. In these reactions it is frequent to observe the presence of naphthalenyl-1H-pyrrole derivatives as a result of a hetero Diels-Alder process, which is competitive with the normal way. The global electrophilic character of the dienophile is responsible of these results. Other dienes (or dienophiles/electrophiles) with electron donor substitution in C-1 show a different behavior in which the hetero Diels-Alder products prevail. In the series explored only the substrate 1-cyano-4-nitronaphthalene produces the naphthalenyl-1H-pyrrole derivative as principal product, probably as a consequence of its charge distribution. A combination between stereoelectronic effects in the electrophile and the type of substitution joint to the nucleophilicity of the diene is responsible of the results and regioselectivity observed in these polar cycloaddition reactions. In all the cases studied the regioselectivity expected by theoretical calculations corresponds with the ones obtained experimentally.

  二硝基萘与(E)-1-三甲基硅氧基-1,3-丁二烯之间的环加成反应产生硝基菲醇衍生物作为主要产物。初级加合物经历不可逆的亚硝酸的损失，因此发生芳构化。在这些反应中，常常会观察到萘基-1H-吡咯衍生物的存在，这是由于异烯烃-Diels-Alder过程的结果，该过程与正常途径竞争。烯烃的整体电亲性特征导致了这些结果。其他在C-1具有电子供体取代基的烯烃（或烯烃亲电体/电亲体）表现出不同的行为，其中异烯烃-Diels-Alder产物占主导地位。在所探讨的系列中，只有底物1-氰基-4-硝基萘产生萘基-1H-吡咯衍生物作为主要产物，这可能是其电荷分布的结果。电亲体中的立体电子效应与烯烃的取代类型及其亲核性相结合，导致了这些极性环加成反应中观察到的结果和区域选择性。在所有研究的案例中，理论计算所预期的区域选择性与实验获得的结果相符。
• CHEMICAL MECHANICAL POLISHING AND WAFER CLEANING COMPOSITION COMPRISING AMIDOXIME COMPOUNDS AND ASSOCIATED METHOD FOR USE
  申请人：Lee Wai Mun

  公开号：US20090130849A1

  公开（公告）日：2009-05-21

  A composition and associated method for chemical mechanical planarization (or other polishing) is described. The composition contains an amidoxime compound and water. The composition may also contain an abrasive and a compound with oxidation and reduction potential. The composition is useful for attaining improved removal rates for metal, including copper, barrier material, and dielectric layer materials in metal CMP. The composition is particularly useful in conjunction with the associated method for metal CMP applications.

  本文描述了一种化学机械平整化（或其他抛光）的组合物及其相关方法。该组合物含有一种酰胺肟化合物和水。该组合物还可以含有磨料和具有氧化还原潜力的化合物。该组合物可用于在金属CMP中获得改进的金属去除速率，包括铜、屏障材料和金属CMP中的介电层材料。该组合物在金属CMP应用的相关方法中特别有用。