2-乙氧基-5-硝基苯胺 | 136-79-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-乙氧基-5-硝基苯胺
• 中文别名: 5-硝基邻氨基苯乙醚；4-硝基-2-氨基苯乙醚4-Nitro-2-aminophenetole
• 英文名称: 2-Amino-4-nitroethoxybenzen
• 英文别名: 4-nitro-p-phenetidine；2-ethoxy-5-nitro-aniline；2-Aethoxy-5-nitro-anilin；5-Nitro-o-phenetidin；4-Nitro-2-amino-phenol-aethylaether；4-Nitro-2-amino-phenetol；2-Ethoxy-5-nitroaniline
• CAS: 136-79-8
• 化学式: C₈H₁₀N₂O₃
• mdl: MFCD01463324
• 分子量: 182.179
• InChiKey: AMMPGYPPRLWMLW-UHFFFAOYSA-N

物化性质

• 熔点：
  96.5°C
• 沸点：
  355.56°C (rough estimate)
• 密度：
  1.2477 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 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：
  81.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2922299090

反应信息

• 作为反应物：
  描述：

  2-乙氧基-5-硝基苯胺 生成 2-ethoxy-5-nitrobenzenediazonium tetrafluoroborate
  参考文献：
  名称：

  Schiemann; Miau, Chemische Berichte, 1933, vol. 66, p. 1180,1183

  摘要：

  DOI：
• 作为产物：
  描述：

  氨基苯乙醚 在 硫酸 、 硝酸 、 溶剂黄146 作用下， 生成 2-乙氧基-5-硝基苯胺
  参考文献：
  名称：

  Reverdin; Duering, Chemische Berichte, 1899, vol. 32, p. 160

  摘要：

  DOI：

文献信息

• Regioselective reduction of substituted dinitroarenes using baker's yeast
  作者：Claire L. Davey、Lawson W. Powell、Nicholas J. Turner、Andrew Wells

  DOI：10.1016/0040-4039(94)80139-8

  日期：1994.10

  A range of substituted dinitroaromatic compounds have been reduced using baker's yeast (Saccharamyces cerevisiae), in some cases with very high selectivity. A model is presented to account for the origin of the selectivity together with a possible mechanism for the reduction.

  使用贝克酵母（Saccharamyces cerevisiae）已经还原了许多取代的二硝基芳族化合物，在某些情况下具有很高的选择性。提出了一个模型来说明选择性的起源以及可能的降低机理。
• Partial Reduction of Dinitroarenes to Nitroanilines with Hydrazine Hydrate
  作者：Nagaraj R. Ayyangar、Uttam R. Kalkote、Ananda G. Lugade、Pandurang V. Nikrad、Vasant K. Sharma

  DOI：10.1246/bcsj.56.3159

  日期：1983.10

  such as hydroxyl and amine groups could be conveniently reduced with 3 molar equivalents of hydrazine hydrate in presence of Raney nickel catalyst in ethanol/1,2-dichloroethane solvent mixture to give a product wherein one of the two nitro groups was reduced to the amino group. The yields of the partial reduction products are good. Under similar conditions alkoxyl substituents in the o,p-position to the

  在阮内镍催化剂的存在下，在乙醇/1,2-二氯乙烷溶剂混合物中，含有羟基和胺基等取代基的二硝基芳烃可以方便地用 3 摩尔当量的水合肼还原得到产物，其中两个硝基之一被还原为氨基。部分还原产物的收率良好。在类似条件下，硝基 o,p 位的烷氧基取代基被肼基取代，得到 2,4-二硝基苯肼作为主要产物。描述还原反应的细节。
• BITTER TASTE MODIFIERS INCLUDING SUBSTITUTED 1-BENZYL-3-(1-(ISOXAZOL-4-YLMETHYL)-1H-PYRAZOL-4-YL)IMIDAZOLIDINE-2,4-DIONES AND COMPOSITIONS THEREOF
  申请人：SENOMYX, INC.

  公开号：US20160376263A1

  公开（公告）日：2016-12-29

  The present invention includes compounds and compositions known to modify the perception of bitter taste, and combinations of said compositions and compounds with additional compositions, compounds, and products. Exemplary compositions comprise one or more of the following: cooling agents; inactive drug ingredients; active pharmaceutical ingredients; food additives or foodstuffs; flavorants, or flavor enhancers; food or beverage products; bitter compounds; sweeteners; bitterants; sour flavorants; salty flavorants; umami flavorants; plant or animal products; compounds known to be used in pet care products; compounds known to be used in personal care products; compounds known to be used in home products; pharmaceutical preparations; topical preparations; cannabis-derived or cannabis-related products; compounds known to be used in oral care products; beverages; scents, perfumes, or odorants; compounds known to be used in consumer products; silicone compounds; abrasives; surfactants; warming agents; smoking articles; fats, oils, or emulsions; and/or probiotic bacteria or supplements.

  本发明涵盖已知用于改变苦味感知的化合物和组合物，以及所述组合物和化合物与额外的组合物、化合物和产品的组合。示例组合物包括以下一种或多种：冷却剂；无活性药物成分；活性药用成分；食品添加剂或食品；调味剂或调味增强剂；食品或饮料产品；苦味化合物；甜味剂；苦味剂；酸味调味剂；咸味调味剂；鲜味调味剂；植物或动物产品；已知用于宠物护理产品中的化合物；已知用于个人护理产品中的化合物；已知用于家用产品中的化合物；制药制剂；局部制剂；大麻衍生或与大麻相关的产品；已知用于口腔护理产品中的化合物；饮料；香味、香水或除臭剂；已知用于消费品中的化合物；硅化合物；磨料；表面活性剂；发热剂；吸烟物品；脂肪、油脂或乳化剂；和/或益生菌或补充剂。
• COMPOUNDS USEFUL AS MODULATORS OF TRPM8
  申请人：Senomyx, Inc.

  公开号：US20170096418A1

  公开（公告）日：2017-04-06

  The present disclosure relates to compounds which are useful as cooling sensation compounds.

  本公开涉及作为冷感化合物有用的化合物。
• Expanding the Substrate Scope of <i>N</i>‐ and <i>O</i>‐Methyltransferases from Plants for Chemoselective Alkylation**
  作者：Emely Jockmann、Fabiana Subrizi、Michael K. F. Mohr、Eve M. Carter、Pia M. Hebecker、Désirée Popadić、Helen C. Hailes、Jennifer N. Andexer

  DOI：10.1002/cctc.202300930

  日期：2023.11.22

  Methylation reactions are of significant interest when generating pharmaceutically active molecules and building blocks for other applications. Synthetic methylating reagents are often toxic and unselective due to their high reactivity. S‐Adenosyl‐l‐methionine (SAM)‐dependent methyltransferases (MTs) present a chemoselective and environmentally friendly alternative. The anthranilate N‐MT from Ruta graveolens (RgANMT) is involved in acridone alkaloid biosynthesis, methylating anthranilate. Although it is known to methylate substrates only at the N‐position, the closest relatives with respect to amino acid sequence similarities of over 60 % are O‐MTs catalysing the methylation reaction of caffeate and derivatives containing only hydroxyl groups (CaOMTs). In this study, we investigated the substrate range of RgANMT and a CaOMT from Prunus persica (PpCaOMT) using compounds with both, an amino‐ and hydroxyl group (aminophenols) as possible methyl group acceptors. For both enzymes, the reaction was highly chemoselective. Furthermore, generating cofactor derivatives in situ enabled the transfer of other alkyl chains onto the aminophenols, leading to an enlarged pool of products. Selected MT reactions were performed at a preparative biocatalytic scale in in vitro and in vivo experiments resulting in yields of up to 62 %.

  摘要 甲基化反应在生成具有医药活性的分子和用于其他应用的构件时具有重要意义。合成甲基化试剂由于反应活性高，通常具有毒性和非选择性。依赖 S-腺苷-l-蛋氨酸（SAM）的甲基转移酶（MTs）提供了一种化学选择性和环境友好型的替代方法。Ruta graveolens 中的蚁酸 N-MT（RgANMT）参与吖啶酮生物碱的生物合成，将蚁酸甲基化。虽然已知它只能在 N 位甲基化底物，但氨基酸序列相似度超过 60% 的近亲是催化咖啡酸酯和仅含羟基的衍生物（CaOMTs）甲基化反应的 O-MTs 。在这项研究中，我们使用同时含有氨基和羟基（氨基苯酚）的化合物作为可能的甲基受体，研究了 RgANMT 和一种来自柿树的 CaOMT（PpCaOMT）的底物范围。这两种酶的反应都具有高度化学选择性。此外，原位生成辅助因子衍生物可以将其他烷基链转移到氨基苯酚上，从而扩大产物库。在体外和体内实验中，以制备生物催化的规模进行了选定的 MT 反应，结果产率高达 62%。