N-(4-乙氧基苯基)羟胺 | 38246-95-6

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: N-(4-乙氧基苯基)羟胺
• 英文名称: N-hydroxyphenetidine
• 英文别名: N-(4-ethoxy-phenyl)-hydroxylamine；N-(4-Aethoxy-phenyl)-hydroxylamin；4-Hydroxylamino-1-aethoxy-benzol；4-Hydroxylamino-phenetol；N-(4-Ethoxyphenyl)-hydroxylamin；N-(4-ethoxyphenyl)hydroxylamine
• CAS: 38246-95-6
• 化学式: C₈H₁₁NO₂
• mdl: MFCD01722030
• 分子量: 153.181
• InChiKey: BZMRNEWNOBBZCH-UHFFFAOYSA-N

物化性质

• 沸点：
  276.1°C (rough estimate)
• 密度：
  1.1577 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  N-(4-乙氧基苯基)羟胺 在 sodium hydroxide 、 氧气 作用下， 反应 4.0h， 生成 非那西丁杂质18
  参考文献：
  名称：

  Synthesis Of N-Arylhydroxylamines by Antimony-Catalyzed Reduction of Nitroarenes

  摘要：

  Metallic antimony catalyzes the reduction of aromatic nitro compounds to the corresponding N-arylhydroxylamines in good yields with NaBH4 under mild conditions. The azoxybenzenes from autoxidation of N-arylhydroxylamines were also obtained in basic conditions.

  DOI：

  10.1080/00397919708006092
• 作为产物：
  描述：

  4-硝基苯乙醚 在 氯化铵 、 锌 作用下， 以 乙醇 、 水 为溶剂， 反应 0.17h， 生成 N-(4-乙氧基苯基)羟胺
  参考文献：
  名称：

  线粒体A胺肟还原组分（mARC）参与异羟肟酸的还原代谢。

  摘要：

  线粒体mid胺肟还原组分是哺乳动物中最近发现的钼酶，与电子转运蛋白细胞色素b5和NADH细胞色素b5还原酶协同作用，催化N氧化结构的还原。这三种成分的酶系统在N还原药物代谢中起主要作用。属于N-羟基化结构的组，异羟肟酸也是mARC系统的潜在底物。异羟肟酸具有多种药理活性，因此经常在候选药物中发现。它们还表现出毒性，就像芳基酰胺代谢过程中形成的许多芳基异羟肟酸一样。使用重组人蛋白，亚细胞猪组织级分以及人细胞培养物进行了生物转化测定。在此，除了减少三种药物之外，还报告了mARC依赖的模型化合物苯氧肟酸的还原。与依赖钼的酶系统的其他已知底物（例如a胺肟前药）相比，此处测得的转化速率较慢，从而反映出不同的异羟肟酸的中等代谢稳定性和口服生物利用度。此外，在选定条件下，mARC系统不会降低止痛非那西丁的有毒N-羟基化代谢产物N-羟基非那西丁。这证实了该成分的高毒性，因为它需要通过其他途径进行解毒。

  DOI：

  10.1124/dmd.118.082453

文献信息

• Mechanism and reactivity in perborate oxidation of anilines in acetic acid
  作者：Chockalingam Karunakaran、Ramasamy Kamalam

  DOI：10.1039/b208199g

  日期：2002.12.6

  Perborate but not percarbonate in acetic acid generates peracetic acid on standing and the peracetic acid oxidation of anilines is fast. The oxidation with a fresh solution of perborate in acetic acid is smooth and second order but the specific oxidation rate increases with increasing [perborate]0 or [boric acid]. Perborate on dissolution affords hydrogen peroxide and a borate; the latter assists the former in the oxidation. The oxidation rates of anilines under identical conditions do not conform to any of the linear free energy relationships but the reaction rates of molecular anilines do. Perborate oxidation proceeds via two reaction paths but the overall oxidation rates of molecular anilines conform to structure–reactivity relationships; the transition states do not differ significantly. Analysis of the oxidation rates of perborate and percarbonate reveals that while perborate oxidation is faster than percarbonate it is at least as selective as the latter.

  在乙酸中，过硼酸盐而非过碳酸盐静置时会产生过乙酸，而过乙酸对苯胺的氧化反应迅速。使用新鲜配制的乙酸过硼酸盐溶液进行氧化反应平稳且具有二级反应特性，但特定的氧化速率随[过硼酸盐]0或[硼酸]浓度的增加而增加。过硼酸盐溶解时产生过氧化氢和硼酸盐；后者在氧化过程中辅助前者。在相同条件下，苯胺的氧化速率不符合任何线性自由能关系，但分子苯胺的反应速率却符合。过硼酸盐氧化通过两条反应路径进行，但分子苯胺的整体氧化速率符合结构-反应活性关系；过渡态的差异不大。对过硼酸盐和过碳酸盐氧化速率的分析显示，尽管过硼酸盐的氧化速率更快，但其选择性至少不亚于过碳酸盐。
• A fast procedure for the reduction of azides and nitro compounds based on the reducing ability of Sn(SR)3-species
  作者：Marti Bartra、Pedro Romea、Fèlix Urpí、Jaume Vilarrasa

  DOI：10.1016/s0040-4020(01)85439-9

  日期：1990.1

  Tin(II) complexes prepared by treatment of SnCl2or Sn(SR)2 with appropriate amounts of RSH and Et3N appear to be the best reducing agents for azides (to amines) reported so far. These tin(II) complexes also reduce primary and secondary aliphatic nitro compounds to oximes, usually within minutes at r.t. or hours in cold, and tertiary aliphatic as well as aromatic nitro compounds to afford the corresponding

  通过用适量的RSH和Et 3 N处理SnCl 2或Sn（SR）2制备的锡（II）络合物似乎是迄今为止报道的叠氮化物（对胺类）的最佳还原剂。这些锡（II）配合物还可以将伯和仲脂肪族硝基化合物还原为肟，通常在室温下在数分钟之内或数小时之内即可还原成肟，而叔脂肪族以及芳香族硝基化合物也可以还原为相应的羟胺。通常，叠氮化物比硝基取代基反应更快，而羰基，亚砜，砜，腈和酯在相同条件下实际上是不反应的。还阐明了Sn（SPh）3-与叠氮化物和硝基化合物反应的一些机理细节。
• 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。
• Process for tinting a resin having a large refractivity index and optical material tinted by the process
  申请人：MITSUBISHI GAS CHEMICAL COMPANY, INC.

  公开号：EP0928802A2

  公开（公告）日：1999-07-14

  A process for tinting a resin comprising dipping the resin into a liquid containing at least one compound selected from the group consisting of polar inorganic compounds and polar organic compounds and subsequently tinting the resin, wherein the resin is obtained by curing by polymerization of a compound alone or a composition comprising the compound, the compound having in the molecule thereof one or more structures represented by the following formula (1): wherein R1 represents a hydrocarbon group having 1 to 10 carbon atoms, R2, R3 and R4 each represents hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, Y represents S or O and n represents 0 or 1. A novel resin comprising the compound having sulfur can be tinted in accordance with the present process.

  一种树脂着色工艺，包括将树脂浸入含有至少一种选自由极性无机化合物和极性有机化合物组成的组中的化合物的液体中，然后对树脂进行着色，其中树脂是通过单独的化合物或含有该化合物的组合物的聚合固化而得到的，该化合物在其分子中具有下式(1)所代表的一个或多个结构： 其中 R1 代表具有 1 至 10 个碳原子的烃基，R2、R3 和 R4 各自代表氢原子或具有 1 至 10 个碳原子的烃基，Y 代表 S 或 O，n 代表 0 或 1。 包含含硫化合物的新型树脂可根据本工艺进行着色。
• Process for producing a resin having a large refractive index
  申请人：MITSUBISHI GAS CHEMICAL COMPANY, INC.

  公开号：EP1006374A2

  公开（公告）日：2000-06-07

  A process for producing a resin having a large refractive index which comprises curing an episulfide compound having one or more epithio structures represented by formula (1) in one molecule by polymerization in the presence of a polymerization catalyst and 0.001 to 3.0 parts by weight of a phenol derivative per 100 parts by weight of the episulfide compound. (R1 represents a hydrocarbon group having 1 to 10 carbon atoms, R2, R3 and R4 each represents hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, Y represents S, O, Se or Te and m and n each represents 0 or 1)

  一种生产大折射率树脂的工艺，包括在聚合催化剂和 0.001 至 3.0 份（重量）苯酚衍生物（每 100 份（重量）环硫化合物中含 0.001 至 3.0 份（重量）苯酚衍生物）存在的情况下，通过聚合固化一分子中具有一个或多个由式（1）表示的表硫结构的环硫化合物。 (R1代表具有 1 至 10 个碳原子的烃基，R2、R3 和 R4 分别代表氢原子或具有 1 至 10 个碳原子的烃基，Y 代表 S、O、Se 或 Te，m 和 n 分别代表 0 或 1)