2-(4-氨基苯基)乙酸乙酯 | 33709-38-5

• 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-(4-氨基苯基)乙酸乙酯
• 英文名称: 4-aminophenethyl acetate
• 英文别名: 2-(4-aminophenyl)ethyl acetate；4-amino-benzeneethyl acetate；Benzeneethanol, 4-amino-, acetate (ester)
• CAS: 33709-38-5
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: SKILLEHGFMDIJB-UHFFFAOYSA-N

物化性质

• 沸点：
  301.7±17.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-氨基苯基)乙酸乙酯 在 potassium carbonate 、 potassium nitrate 作用下， 以 甲醇 为溶剂， 生成 2-(4-amino-3-nitrophenyl)ethanol
  参考文献：
  名称：

  2-Arylindoles as gonadotropin releasing hormone (GnRH) antagonists: optimization of the tryptamine side chain

  摘要：

  A series of 2-arylindoles containing novel heteroaromatic substituents on the tryptamine tether, based on compound 1, was prepared and evaluated for their ability to act as gonadotropin releasing hormone (GnRH) antagonists. Successful modifications of 1 included chain length variation (reduction) and replacement of the pyridine with heteroaromatic groups. These alterations culminated in the discovery of compound 27kk which had excellent in vitro potency and oral efficacy in rodents. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00026-4
• 作为产物：
  描述：

  2-(4-硝基苯基)乙基乙酸酯 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 为溶剂， 以78%的产率得到2-(4-氨基苯基)乙酸乙酯
  参考文献：
  名称：

  2-Arylindoles as gonadotropin releasing hormone (GnRH) antagonists: optimization of the tryptamine side chain

  摘要：

  A series of 2-arylindoles containing novel heteroaromatic substituents on the tryptamine tether, based on compound 1, was prepared and evaluated for their ability to act as gonadotropin releasing hormone (GnRH) antagonists. Successful modifications of 1 included chain length variation (reduction) and replacement of the pyridine with heteroaromatic groups. These alterations culminated in the discovery of compound 27kk which had excellent in vitro potency and oral efficacy in rodents. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00026-4

文献信息

• Practical Chemoselective Acylation: Organocatalytic Chemodivergent Esterification and Amidation of Amino Alcohols with <i>N</i> ‐Carbonylimidazoles
  作者：Hope Nelson、William Richard、Hailee Brown、Abigail Medlin、Christina Light、Stephen T. Heller

  DOI：10.1002/anie.202107438

  日期：2021.10.11

  DBU-catalyzed esterification: A single esterification product was obtained from a molecule containing primary aniline, alcohol, phenol, secondary amide, and N−H indole groups. These acylation reactions are highly practical as they involve only readily available, inexpensive, and relatively safe reagents; can be performed on a multigram scale; and can be used on carboxylic acids directly by in situ formation

  化学选择性转化是高效有机合成的基石；然而，即使是简单的转化，如酰化反应，要实现这一目标也常常是一个挑战。我们报告说，N-羰基咪唑分别在吡啶鎓离子或 1,8-二氮杂双环 [5.4.0] undec-7-ene (DBU) 存在下能够催化化学发散的苯胺或醇酰化。两种酰化反应都显示出对目标基团的高而广泛的化学选择性。在 DBU 催化的酯化中观察到了前所未有的化学选择性水平：从含有伯苯胺、醇、苯酚、仲酰胺和N的分子中获得单一酯化产物-H吲哚基团。这些酰化反应非常实用，因为它们只涉及容易获得、便宜且相对安全的试剂；可以在多克规模上进行；并且可以通过原位形成酰基咪唑亲电试剂直接用于羧酸。
• Derivatives of purine, their preparation process and pharmaceutical compositions containing them
  申请人：Haesslein Jean-Luc

  公开号：US20050187228A1

  公开（公告）日：2005-08-25

  A compound of the formula wherein R is defined as in the specification, which compounds have an inhibitory effect vis-à-vis cycline-dependent kinase proteins (cdk) and are endowed with antimitotic properties.

  其中R在规范中定义，该化合物具有对细胞周期依赖性激酶蛋白（cdk）具有抑制作用并具有抗有丝分裂特性。
• A USEFUL METHOD FOR SELECTIVE ACYLATION OF ALCOHOLS USING 2,2′-BIPYRIDYL-6-YL CARBOXYLATE AND CESIUM FLUORIDE
  作者：Teruaki Mukaiyama、Fong-Chang Pai、Makoto Onaka、Koichi Narasaka

  DOI：10.1246/cl.1980.563

  日期：1980.5.5

  Primary and secondary alcohols are acylated under mild conditions by the use of 2,2′-bipyridyl-6-yl carboxylates and cesium fluoride. Furthermore, the reaction is successfully applied to selective acylation of a primary carbinol group of diols containing primary and secondary carbinol groups or exclusive O-acylation of aromatic amino alcohols.

  伯醇和仲醇在温和条件下通过使用 2,2'-联吡啶-6-基羧酸盐和氟化铯进行酰化。此外，该反应成功地应用于含有伯和仲甲醇基团的二醇的伯醇基团的选择性酰化或芳香氨基醇的排他性O-酰化。
• [EN] IMIDAZOLE AND TRIAZOLE DERIVATIVES USEFUL AS SELECTIVE COX-1 INHIBITORS<br/>[FR] DERIVES D'IMIDAZOLE ET DE TRIAZOLE UTILES EN TANT QU'INHIBITEURS DE COX-1 SELECTIFS
  申请人：FUJISAWA PHARMACEUTICAL CO

  公开号：WO2004060367A1

  公开（公告）日：2004-07-22

  A compound of the formula (I): or salts thereof, which are useful for treatment and/or prevention of inflammatory conditions, various pains, collagen diseases, autoimmune diseases, thrombosis, cancer or neurodengenerative diseases.

  一种具有以下化学式（I）的化合物，或其盐，可用于治疗和/或预防炎症性疾病、各种疼痛、胶原病、自身免疫疾病、血栓形成、癌症或神经退行性疾病。
• N-Aryl-N'-(phenyl-or phenoxy-alkyl)-piperazines and salts thereof
  申请人：Boehringer Ingelheim GmbH

  公开号：US03941789A1

  公开（公告）日：1976-03-02

  Compounds of the formula ##EQU1## wherein R is phenyl; phenyl having one or more substituents attached thereto, said substituents being selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, halogen and trifluoromethyl; a bicyclic aromatic or cycloaliphatic-aromatic ring, especially naphthyl, tetrahydronaphthyl or indanyl; or a mono- or bicyclic heterocyclic ring, especially pyridyl, pyrimidyl, isoquinolyl or thiazolyl; R.sub.1 is ##EQU2## where B is ##EQU3## n is 2, 3 or 4, R.sub.3 is hydrogen, alkyl of 1 to 4 carbon atoms or alkanoyl of 1 to 4 carbon atoms, R.sub.4 and R.sub.5, which may be identical to or different from each other, are each hydrogen or alkyl of 1 to 4 carbon atoms, p is 0 or 1, and Q is oxygen or two hydrogens, R.sub.2 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen, A is a single carbon-to-carbon bond or --OCH.sub.2 --, R.sub.6 is hydrogen, hydroxyl, alkoxy of 1 to 4 carbon atoms or alkanoyloxy of 1 to 4 carbon atoms, and m is 0, 1, 2, 3, 4 or 5, but other than 0 when R.sub.6 is hydroxyl, And non-toxic, pharmacologically acceptable acid addition salts thereof; the compounds as well as their salts are useful as CNS-depressants, adrenolytics, antiphologistics, analgesics, antihistamines and anticholesterols.

  化合物的公式为##EQU1##其中R是苯基;苯基上有一个或多个取代基，所述取代基选择自1至4个碳原子的烷基，1至4个碳原子的烷氧基，1至4个碳原子的烷硫基，卤素和三氟甲基;一个双环芳香族或环烷基-芳香族环，特别是萘基，四氢萘基或茚基; 或者是一个单环或双环杂环，特别是吡啶基，嘧啶基，异喹啉基或噻唑基; R.sub.1是##EQU2##其中B是##EQU3##n是2、3或4，R.sub.3是氢，1至4个碳原子的烷基或1至4个碳原子的脂肪酰基，R.sub.4和R.sub.5，它们可以相同也可以不同，都是氢或1至4个碳原子的烷基，p是0或1，Q是氧或两个氢，R.sub.2是氢，1至4个碳原子的烷基，1至4个碳原子的烷氧基或卤素，A是单个碳-碳键或--OCH.sub.2 --，R.sub.6是氢，羟基，1至4个碳原子的烷氧基或1至4个碳原子的脂肪酰氧基，m是0、1、2、3、4或5，但当R.sub.6是羟基时，m不为0，并且其非毒性、药理学上可接受的酸盐;这些化合物及其盐可用作中枢神经系统抑制剂、肾上腺素能拮抗剂、抗炎剂、镇痛剂、抗组胺剂和降胆固醇剂。