1-乙氧基-4-亚硝基苯 | 3420-97-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-乙氧基-4-亚硝基苯
• 英文名称: 1-ethoxy-4-nitrosobenzene
• 英文别名: p-ethoxynitrosobenzene；4-nitrosophenetole；p-nitrosophenetole；4-nitroso-phenetole；4-Nitroso-1-aethoxy-benzol；4-Nitroso-phenetol
• CAS: 3420-97-1
• 化学式: C₈H₉NO₂
• 分子量: 151.165
• InChiKey: ZGWJGKWXNVDMII-UHFFFAOYSA-N

物化性质

• 熔点：
  31.5-33 °C
• 沸点：
  245.4±23.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2909309090

反应信息

• 作为反应物：
  描述：

  1-乙氧基-4-亚硝基苯 以 甲醇 为溶剂， 反应 72.0h， 生成 4-亚硝基苯酚
  参考文献：
  名称：

  Additional Pathways of S-Conjugate Formation during Interaction of 4-Nitrosophenetole with Glutathione

  摘要：

  The rapid reactions of nitrosoarenes with cellular SH groups have proved to be main metabolic conversions during detoxication. Inter actions of the phenacetin metabolite 4-nitrosophenetole with glutathione have been investigated in detail during the last years, revealing a complete pattern of products depending on the stoichiometry of the reactants and reaction conditions Eight metabolites have been identified hitherto, and the present work extends this medley by six additional products. Three metastable sulfenamides, 4-ethoxy-2,N-bis(glutathion-S-yl)-aniline, N-4-glutathion-S-yl)-4-amino-4'-ethoxydiphenylamine, and N-(glutathion-S-yl)-4-aminophenol, as well as the N-sulfenylquinonimine N-(glutathion-S-yl)-1,4-benzoquinonimine were characterized by chemical reactivity, chromatographic behavior, UV/vis absorption, H-1 NMR, and FAB-MS data. The structure of the sulfenamide 2,N-4-bis(glutathion-S-yl)-4-amino-4'-ethoxydiphenylamine could not be proved unequivocally, but is strongly suggested due to the chemical reactivity? chromatographic behavior, and UV/vis absorption of the compound. Finally, traces of 4-aminophenol were detected. A reaction scheme is presented explaining the formation of all identified metabolites via a central sulfenamide cation. Molecular orbital calculations for this sulfenamide cation have been performed, corroborating the proposed reaction mechanisms on the basis of Klopman's generalized perturbation theory.

  DOI：

  10.1021/tx980087q
• 作为产物：
  描述：

  苯乙醚 在 nitrosonium ethyl sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以30%的产率得到1-乙氧基-4-亚硝基苯
  参考文献：
  名称：

  用亚硝基乙基硫酸盐硝化芳烃

  摘要：

  亚硝基乙基硫酸盐与 O-烷基苯酚和 N,N-二烷基苯胺反应生成相应的 4-亚硝基芳烃。该反应不伴随常见亚硝化剂的副反应。用亚硝基乙基硫酸盐重氮化伯芳香胺产生稳定的重氮盐，这是有机合成的有前途的试剂。

  DOI：

  10.1007/bf02496170

文献信息

• New nitrite ionic liquid (IL-ONO) and nanoparticles of organosilane-based nitrite ionic liquid immobilized on silica as nitrosonium sources for electrophilic aromatic nitrosation
  作者：Hassan Valizadeh、Mohammad Amiri、Ashkan Shomali

  DOI：10.1016/j.crci.2011.09.012

  日期：2011.12

  improved method for the synthesis of nitrosoarenes has been developed using a new nitrite ionic liquid (IL-ONO) and immobilized nitrite ionic liquid. These ionic liquids play as nitrosonium sources for electrophilic aromatic nitrosation of active aromatics at 0–5 °C. Their action was accomplished in water and the satisfactory results were obtained under the mild conditions in short reaction time.

  摘要 利用新型亚硝酸离子液体 (IL-ONO) 和固定化亚硝酸离子液体开发了一种合成亚硝基芳烃的改进方法。这些离子液体在 0–5 °C 下作为活性芳烃的亲电芳族亚硝化的亚硝基源。它们的作用是在水中完成的，在温和的条件下，在很短的反应时间内获得了令人满意的结果。
• Mechanism of metabolic activation of the analgetic bucetin to bacterial mutagens by hamster liver microsomes.
  作者：TAKEHIKO NOHMI、MOTOI JR. ISHIDATE、AKIRA HIRATSUKA、TADASHI WATABE

  DOI：10.1248/cpb.33.2877

  日期：——

  Bucetin (N-(β-hydroxybutyryl)-p-phenetidine) was found to be mutagenic to Salmonella typhimurium TA100 in the presence of liver 9000g supernatant fractions (S9) prepared from polychlorinated biphenyl (PCB)-treated hamsters and a reduced nicotinamide adenine dinucleotidephosphate (NADPH)-generating system. However, the analgetic was not mutagenic in the presence of NADPH-fortified S9 from PCB-treated rat liver. The mutagenic potency of bucetin was about a quarter of that of the structurally related analgetic, phenacetin. PCB-treated hamster liver microsomes fortified with NADPH activated bucetin to two direct-acting mutagens, N-hydroxyphenetidine and p-nitrosophenetole, through deacylation followed by N-hydroxylation. The nitroso compound arose from N-hydroxyphenetidine via autoxidation. N-(β-Hydroxybutyryl)-p-aminophenol, a major metabolite of bucetin under the conditions used, was not mutagenic to TA 100 either with or without NADPH-fortified S9 from PCB-treated or untreated rats or hamsters. N-Hydroxybucetin, which was about 70 times less mutagenic than N-hydroxyphenacetin in the presence of PCB-treated hamster S9, was not detected as a metabolite of bucetin from the NADPH-fortified reaction mixtures. Although no species difference was observed in p-phenetidine N-hydroxylation, the rate of bucetin deacylation was over 90 times higher in hamsters than in rats. The rate of microsomal deacylation of bucetin was much lower than that of phenacetin or N-butyryl-p-phenetidine. These results suggest that the species difference in bucetin mutagenicity is due to the difference in deacylating activity between rat and hamster liver microsomes, and also that the β-hydroxyl group in the butyryl side chain makes bucetin poorly hydrolyzable in microsomes, resulting in lower mutagenic activity as compared with phenacetin.

  研究发现，在多氯联苯（PCB）处理仓鼠肝脏 9000g 上清液馏分（S9）和还原型烟酰胺腺嘌呤二核苷酸（NADPH）生成系统存在的情况下，Bucetin（N-(β-羟基丁酰)-p-苯乙啶）对鼠伤寒沙门氏菌 TA100 具有诱变作用。然而，在来自经多氯联苯（PCB）处理的大鼠肝脏的强化 NADPH S9 存在的情况下，该镇痛剂不具有诱变性。布塞汀的诱变效力约为结构相关的镇痛药苯乙哌啶的四分之一。经 NADPH 强化的多氯联苯处理仓鼠肝脏微粒体通过脱乙酰化和 N-羟基化将布克汀活化为两种直接作用的诱变剂--N-羟基苯乙啶和对亚硝基苯乙醚。亚硝基化合物是由 N-羟基苯乙啶通过自氧化作用生成的。在使用条件下，N-（β-羟基丁酰）-p-氨基苯酚是丁香酚的主要代谢物，无论是否添加 NADPH 强化 S9，都不会对来自 PCB 处理过或未处理过的大鼠或仓鼠的 TA 100 产生诱变作用。在有 PCB 处理过的仓鼠 S9 存在的情况下，N-羟基白屈菜素的诱变性比 N-羟基苯乙酮低约 70 倍，但在 NADPH 强化的反应混合物中未检测到白屈菜素的代谢物。虽然在对苯乙啶 N-羟基化过程中没有观察到物种差异，但仓鼠的丁香酚脱乙酰率比大鼠高 90 多倍。与苯乙酸或 N-丁酰基对苯乙哌啶相比，丁香酮苷的微粒体脱乙酰率要低得多。这些结果表明，布塞汀致突变性的物种差异是由于大鼠和仓鼠肝脏微粒体的脱乙酰活性不同造成的，而且丁酰侧链中的β-羟基使布塞汀在微粒体中的水解性差，导致其致突变活性低于苯乙哌啶。
• ISOCYANATE TERMINATED MACROMER AND FORMULATION THEREOF FOR USE AS AN INTERNAL ADHESIVE OR SEALANT
  申请人：Khatri Chetan Anirudh

  公开号：US20100158849A1

  公开（公告）日：2010-06-24

  A novel macromer or mixture thereof is described herein, comprising isocyanatophenyl ether terminal moieties and at least two residues of a water-soluble polymer having a molecular weight ranging from 80 to 10,000 adjacent to the ether group of the isocyanatophenyl ether terminal isocyanate moieties, thereby forming at least two ether linkages in the macromer or mixture thereof. A method for making a polyisocyanate macromer is also described herein.

  本文描述了一种新型大分子单体或其混合物，包括异氰酸苯醚端基团和至少两个分子量范围从80到10,000的水溶性聚合物残基，这些残基与异氰酸苯醚端基异氰酸酯基团相邻，从而在大分子单体或其混合物中形成至少两个醚键。本文还描述了一种制备聚异氰酸酯大分子单体的方法。
• Formation of 4,4-Dialkoxycyclohexa-2,5-dienone <i>N</i>-(Thiol-<i>S</i>-yl)imine during Reaction of 4-Alkoxynitrosobenzenes with Thiols in Alcoholic Solvents
  作者：Dieter Gallemann、Anke Greif、Peter Eyer、Johannes Dasenbrock、Elmar Wimmer、Johann Sonnenbichler、Isolde Sonnenbichler、Wolfram Schäfer、Ingrid Buhrow

  DOI：10.1021/tx980088i

  日期：1998.12.1

  During the interaction of nitrosoarenes with glutathione in aqueous media, intermediate generation of a highly resonance-stabilized sulfenamide cation has been repeatedly suggested. Most intermediates and end products could be explained by reactions of this sulfenamide cation with different nucleophiles such as excess thiol, solvent water, and metabolically produced arylamine. The present paper presents

  在水介质中亚硝基芳烃与谷胱甘肽的相互作用过程中，已经多次提出了高度共振稳定的次磺酰胺阳离子的中间生成。多数中间体和终产物可以通过该次磺酰胺阳离子与不同亲核试剂（例如过量的硫醇，溶剂水和代谢产生的芳胺）的反应来解释。本文提供了在中性pH下亚砜酰胺阳离子与溶剂醇加成形成的证据。强烈建议分别由4-亚硝基苯酚和4-亚硝基苯甲醚生成的亚磺酰胺阳离子形成亚稳缩酮4-乙氧基-4-甲氧基环己2,5-二烯酮N-（谷胱甘肽-S-基）亚胺和4,4-在与溶剂甲醇反应期间，分别将二甲氧基环己-2,5-二烯酮N-（谷胱甘肽-S-基）亚胺。两个亚磺酰胺阳离子在乙醇中的反应产生4,4-二乙氧基环己-2，5-二烯酮N-（谷胱甘肽-S-基）亚胺和4-乙氧基-4-甲氧基环己-2，5-二烯酮N-（谷胱甘肽-S -yl）亚胺。尽管缩酮的亚稳定性不允许分离纯固体物质，但色谱和化学行为以及串联MS碎片证实了这些中间体的缩酮结构。为了确
• Processes for production of alpha-aminooxyketones and alpha-hydroxyketones
  申请人：Saito Susumu

  公开号：US20070055081A1

  公开（公告）日：2007-03-08

  The present invention provides a method for easily obtaining α-aminooxyketone compound which is a synthetic equivalent for monosaccharide and pentoses, and a equivalent of α-hydroxyketone compound that can be synthetic intermediates of various physiologically active materials, in high yield; to pave the way for the synthesis of monosaccharide and furthermore of oligosaccharide from the resulting α-hydroxyketone compound induced from α-aminooxyketone compound; and to open new possibilities for the synthesis of various sugar medicines such as anticancer agents, antithrombogenic agents, anti-viral agents, anti-HIV agents, inhibitors of cholesterol synthesis, verotoxin neutralizing agents. According to the invention, a carbonyl compound is allowed to react with a nitroso compound to produce an α-aminooxyketone compound using a catalyst containing a heterocyclic compound shown in the general formula (I) (wherein X1, X2 and X3 independently represent nitrogen, carbon, oxygen or sulfur; and Z represents a substituted or unsubstituted 5- to 10-membered ring).

  本发明提供了一种方法，以高产率轻松获得α-氨氧酮化合物，该化合物是单糖和戊糖的合成等效物，以及α-羟基酮化合物的等效物，可用作各种生理活性物质的合成中间体，为从α-氨氧酮化合物诱导的α-羟基酮化合物合成单糖并进一步合成寡糖铺平道路，并为合成各种糖类药物如抗癌剂、抗凝血剂、抗病毒剂、抗HIV剂、胆固醇合成抑制剂、痢疾毒素中和剂开辟新的可能性。根据本发明，允许羰基化合物与亚硝基化合物反应，使用包含在一般式（I）中的杂环化合物的催化剂（其中X1、X2和X3独立地表示氮、碳、氧或硫；Z表示取代或未取代的5至10元环）。