2-乙酰氨基-5-氯苯甲醛 | 53165-18-7

• 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-乙酰氨基-5-氯苯甲醛
• 英文名称: N-(4-chloro-2-formylphenyl)acetamide
• CAS: 53165-18-7
• 化学式: C₉H₈ClNO₂
• 分子量: 197.621
• InChiKey: NEPFJGOQXMFVOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-乙酰氨基-5-氯苯甲醛 在 potassium dihydrogenphosphate 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以82%的产率得到1-(5-氯-1H-吲唑-1-基)乙酮
  参考文献：
  名称：

  Conjugate base catalysed one-pot synthesis of pyrazoles from β-formyl enamides

  摘要：

  A novel one-pot synthesis of pyrazoles has been accomplished by the reaction of beta-formyl enamides with hydroxylamine hydrochloride catalysed by potassium dihydrogeriphosphate in acid medium. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.145
• 作为产物：
  描述：

  N-(2-甲酰基苯基)乙酰胺 在 N-氯代丁二酰亚胺 作用下， 生成 2-乙酰氨基-5-氯苯甲醛
  参考文献：
  名称：

  A General Synthesis of Novel Quinoline-Based Isoindolin-1-one Derivatives

  摘要：

  A simple and general one-pot protocol for the synthesis of a series quinoline-based isoindolin-l-ones, namely 7-chloro-2-substituted-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-l-ones (5a-p) is described, involving a cascade Williamson-type condensation reaction of ethyl 6-chloro-2-(chloromethyl)quinoline-3-carboxylate (3) with aromatic amines (4 a-i), aliphatic amines (4j-m) and aliphatic diamines (4n-p) and subsequent intramolecular C-N bond cyclization of the resulting intermediates in refluxing EtOH-AcOH (v/v, 10:1) solvent system in a single synthetic operation.

  DOI：

  10.3987/com-15-13314

文献信息

• Identification of Potent Ebola Virus Entry Inhibitors with Suitable Properties for in Vivo Studies
  作者：Hu Liu、Ye Tian、Kyungae Lee、Pranav Krishnan、May Kwang-Mei Wang、Sean Whelan、Emily Mevers、Veronica Soloveva、Benjamin Dedic、Xinyong Liu、James M. Cunningham

  DOI：10.1021/acs.jmedchem.8b00704

  日期：2018.7.26

  an adamantane dipeptide piperazine 3.47 that inhibits Ebola virus (EBOV) infection by targeting the essential receptor Niemann–Pick C1 (NPC1). The physicochemical properties of 3.47 limit its potential for testing in vivo. Optimization by improving potency, reducing hydrophobicity, and replacing labile moieties identified 3.47 derivatives with improved in vitro ADME properties that are also highly

  先前的研究确定了金刚烷二肽哌嗪3.47，其通过靶向必需受体Niemann–Pick C1（NPC1）抑制埃博拉病毒（EBOV）感染。3.47的理化特性限制了其在体内测试的潜力。通过提高效力，降低疏水性和取代不稳定部分进行优化，确定为3.47具有改善的体外ADME特性的衍生物，对EBOV感染也具有很高的活性，包括在50％正常人血清（NHS）存在下进行测试时。此外，3A4被认为是代谢这些化合物的主要细胞色素P450亚型，因此，在存在CYP3A4抑制剂ritonavir的存在下进行测试时，小鼠微粒体的稳定性得到了显着改善，该药物已被批准用于临床作为抗HIV药物的增强剂。EBOV抑制剂与利托那韦的口服给药产生的药代动力学特征支持了用于小鼠功效研究的双向给药方案。
• Substituted Aryl Benzylamines as Potent and Selective Inhibitors of 17β-Hydroxysteroid Dehydrogenase Type 3
  作者：Nigel Vicker、Helen V. Bailey、Joanna M. Day、Mary F. Mahon、Andrew Smith、Helena J. Tutill、Atul Purohit、Barry V. L. Potter

  DOI：10.3390/molecules26237166

  日期：——

  low nanomolar IC50 17β-HSD3 inhibitors were discovered using N-(2-([2-(4-chlorophenoxy)phenylamino]methyl)phenyl)acetamide (1). The most potent compounds have IC50 values of approximately 75 nM. Compound 29, N-[2-(1-Acetylpiperidin-4-ylamino)benzyl]-N-[2-(4-chlorophenoxy)phenyl]acetamide, has an IC50 of 76 nM, while compound 30, N-(2-(1-[2-(4-chlorophenoxy)-phenylamino]ethyl)phenyl)acetamide, has an IC50

  17β-羟基类固醇脱氢酶 3 型 (17β-HSD3) 在睾丸和精囊中高水平表达；它也存在于前列腺组织中，并参与性腺和非性腺睾酮的生物合成。该酶是膜结合的，还没有晶体结构。使用先前建立的同源模型和对接研究，通过基于结构的设计，设计并合成了基于选择性芳基苄胺的抑制剂作为前列腺癌治疗的潜在药物。使用N- (2-([2-(4-氯苯氧基)苯基氨基]甲基)苯基)乙酰胺 ( 1 )发现了有效的、选择性的、低纳摩尔 IC 50 17β-HSD3 抑制剂。最有效的化合物具有大约 75 nM 的 IC 50值。化合物29 , N -[2-(1-Acetylpiperidin-4-ylamino)benzyl] -N -[2-(4-chlorophenoxy)phenyl]acetamide, IC 50为 76 nM，而化合物30 , N -(2- (1-[2-(4-氯苯氧基)-苯基氨基]乙基)苯基)乙酰胺，IC
• Synthesis of Methyl 2-Amino-3<i>H</i>-1-benzazepine-4-carboxylates and 2-(Cyanomethyl)-2,3-dihydro-1<i>H</i>-indole-2-carboxylates from Morita-Baylis-Hillman Acetates of 2-(Acylamino)benzaldehydes
  作者：Kee-Jung Lee、Hee Lim、Young Song

  DOI：10.1055/s-2007-990809

  日期：2007.11

  Methyl 2-Amino-3H-1-benzazepine-4-carboxylates or methyl 2-(cyanomethyl)-2,3-dihydro-1H-indole-2-carboxylates were prepared from the reaction of 3-[2-formamido-, 2-acetamido-, or 2-(propanoylamino)phenyl]-substituted methyl 2-(cyanomethyl)propenoates with sodium methoxide in methanol, respectively. The latter were readily obtained from the Morita-Baylis-Hillman reaction of N-protected 2-aminobenzaldehydes with methyl acrylate followed by acetylation and cyanation.

  2-氨基-3H-1-苯并氮杂卓-4-羧酸甲酯或 2-(氰甲基)-2,3-二氢-1H-吲哚-2-羧酸甲酯分别由 3-[2-甲酰胺基、2-乙酰胺基或 2-(丙酰氨基)苯基]-取代的 2-(氰甲基)丙烯酸甲酯与甲醇中的甲醇钠反应制备而成。后者很容易从 N 保护的 2-氨基苯甲醛与丙烯酸甲酯的 Morita-Baylis-Hillman 反应中获得，然后进行乙酰化和氰化。
• Iron-catalyzed aerobic oxidative cleavage of the C–C σ-bond using air as the oxidant: chemoselective synthesis of carbon chain-shortened aldehydes, ketones and 1,2-dicarbonyl compounds
  作者：Qi Xing、Hui Lv、Chungu Xia、Fuwei Li

  DOI：10.1039/c5cc07390a

  日期：——

  A simple iron-catalyzed aerobic oxidative C-C [sigma]-bond cleavage of ketones has been developed. Readily available and environmently benign air is used as the oxidant. This reaction prevents the use of...

  已经开发了酮的简单的铁催化的需氧氧化CCσ键裂解。易获得且对环境无害的空气用作氧化剂。该反应阻止使用...
• A Copper-Catalyzed Cascade Approach for the Synthesis of Dibenzo[<i>b,f</i> ]1,8-naphthyridine Derivatives
  作者：Bharath Kumar Villuri、Ashok Konala、Veerababurao Kavala、Trimurtulu Kotipalli、Chun-Wei Kuo、Ching-Fa Yao

  DOI：10.1002/adsc.201700546

  日期：2017.9.18

  The synthesis of some dibenzo[b,f]‐[1,8]naphthyridine derivatives in a cascade manner is reported. The reaction includes a Knovenagel condensation, the insertion of a nitrile and an alkyne into an N–H bond and an oxidation/oxidative C–C bond cleavage sequence in the presence of copper iodide. The key 1,8‐naphthyridine core was constructed in a cascade manner during the course of the reaction itself

  据报道以级联方式合成了一些二苯并[ b，f ]-[1,8]萘啶衍生物。该反应包括Knovenagel缩合反应，在碘化铜存在下，将腈和炔插入到NH键中，以及氧化/氧化CC键的裂解顺序。关键的1,8-萘啶核心是在反应过程中以级联方式构建的，可以轻松制备各种二苯并[ b，f ]-[1,8]萘啶衍生物。