N-benzyl-N-[2-(4-nitrophenyl)ethyl]amine | 211635-75-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-N-[2-(4-nitrophenyl)ethyl]amine
• 英文别名: N-benzyl-2-(4-nitrophenyl)ethan-1-amine；N-benzyl-2-(4-nitrophenyl)ethanamine；N-benzyl-2-(4-nitrophenyl)ethylamine；N-benzyl-4-nitrophenethylamine；N-benzyl-p-nitrophenethylamine；benzyl-(4-nitro-phenethyl)-amine；[(4-Nitrophenyl)ethyl]benzylamine
• CAS: 211635-75-5
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: YIBHHPKCUYKTTB-UHFFFAOYSA-N

物化性质

• 沸点：
  414.0±25.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-[2-(4-nitrophenyl)ethyl]amine 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 乙酸乙酯 、 正丁醇 为溶剂， 反应 4.0h， 生成 (2R)-hydroxy-2-phenylacetyl-4’-[2-[((2R)hydroxy-2-phenyl)ethylamino]ethyl]acetanilide
  参考文献：
  名称：

  [EN] METHOD FOR THE PRODUCTION OF MORPHOLOGICALLY HOMOGENOUS MIRABEGRON AND MIRABEGRON MONOHYDROCHLORIDE
  [FR] PROCÉDÉ DE PRODUCTION DE MIRABEGRON MORPHOLOGIQUEMENT HOMOGÈNE ET DE MONOCHLORHYDRATE DE MIRABEGRON

  摘要：

  本发明的对象涉及一种生产化合物1（R）-2-(2-氨基噻唑-4-基)-4'-[2-[(2-羟基-2-苯基)乙基氨基]乙基]乙酰苯胺（米拉贝隆）和化合物1c 米拉贝隆单盐酸盐的方法，以及在该方法中使用的中间体。

  公开号：

  WO2017137784A1
• 作为产物：
  描述：

  4-硝基苯乙胺 在 钾硼氢 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 N-benzyl-N-[2-(4-nitrophenyl)ethyl]amine
  参考文献：
  名称：

  New p-Methylsulfonamido Phenylethylamine Analogues as Class III Antiarrhythmic Agents:  Design, Synthesis, Biological Assay, and 3D-QSAR Analysis

  摘要：

  Class III antiarrhythmic agents selectively delay the effective refractory period (ERP) and increase the transmembrance action potential duration (APD). Using dofetilide (2) as a template of class III antiarrhythmic agents, we designed and synthesized 16 methylsulfonamido phenylethylamine analogues (4a-d and 5a-1). Pharmacological assay indicated that all of these compounds showed activity for increasing the ERP in isolated animal atrium; among them, the effective concentration of compound 4a is 1.6 x 10(-8) mol/L in increasing ERP by 10 ms, slightly less potent than that of 2, 1.1 x 10(-8) mol/L. Compound 4a also produced a slightly lower change in ERP at 10(-5) M, DeltaERP% = 17.5% (DeltaERP% = 24.0% for dofetilide). On the basis of this bioassay result, these 16 compounds together with dofetilide were investigated by the three-dimensional quantitative structure-activity relationship (3D-QSAR) techniques of comparative molecular field analysis (CoMFA), comparative molecular similarity index analysis (CoMSIA), and the hologram QSAR (HQSAR). The 3D-QSAR models were tested with another 11 compounds (4e-h and 5m-s) that we synthesized later. Results revealed that the CoMFA, CoMSIA, and HQSAR predicted activities for the 11 newly synthesized compounds that have a good correlation with their experimental value, r(2) = 0.943, 0.891, and 0.809 for the three QSAR models, respectively. This indicates that the 3D-QSAR models proved a good predictive ability and could describe the steric, electrostatic, and hydrophobic requirements for recognition forces of the receptor site. On the basis of these results, we designed and synthesized another eight new analogues of methanesulfonamido phenylethyamine (6a-h) according to the clues provided by the 3D-QSAR analyses. Pharmacological assay indicated that the effective concentrations of delaying the ERP by 10 ins of these newly designed compounds correlated well with the 3D-QSAR predicted values. It is remarkable that the percent change of delaying ERP at 10-5 M compound 6c is much higher than that of dofetilide; the effective concentration of compound 6c is 5.0 x 10(-8)mol/L in increasing the ERP by 10 Ms, which is slightly lower than that of 2. The results showed that the 3D-QSAR models are reliable and can be extended to design new antiarrhythmic agents.

  DOI：

  10.1021/jm010574u

文献信息

• Nucleophilic additions to polarized vinylarenes
  作者：Krishna Kumar Gnanasekaran、Junghak Yoon、Richard A. Bunce

  DOI：10.1016/j.tetlet.2016.06.033

  日期：2016.7

  substituents on the side chain double bond. The study revealed that nitro substitution gave the best results for addition of carbon and nitrogen nucleophiles. Cyano-substituted systems added carbon nucleophiles, but underwent polymerization or degradation with nitrogen nucleophiles. Ethoxycarbonyl-bearing substrates reacted primarily at the ester carbonyl. The reaction generally proceeded well with methyl

  将亲核试剂加到在邻位或对位结合了吸电子基团的苯乙烯的末端双键碳上位置已被研究。已经优化了该转化的条件，并且已经探索了对底物的结构修饰。结构变化包括芳环上活化基的变化和侧链双键上的定位取代基。研究表明，硝基取代对于碳和氮亲核试剂的添加效果最佳。氰基取代的系统添加了碳亲核试剂，但是经过了氮亲核试剂的聚合或降解。带有乙氧基羰基的底物主要在酯羰基上反应。通常，在双键的α碳上有甲基的情况下，反应进行得很好，但在β位置的甲基会使反应变慢。对于22个实例，产率从50％变化到97％。
• Substituted benzazoles and methods of their use as inhibitors of Raf kinase
  申请人：——

  公开号：US20040122237A1

  公开（公告）日：2004-06-24

  New substituted benz-azole compounds, compositions and methods of inhibition of Raf kinase activity in a human or animal subject are provided. The new compounds compositions may be used either alone or in combination with at least one additional agent for the treatment of a Raf kinase mediated disorder, such as cancer.

  提供了新的替代苯唑化合物、组合物和抑制人类或动物主体中Raf激酶活性的方法。这些新化合物组合物可以单独使用，也可以与至少一种额外药物结合，用于治疗由Raf激酶介导的疾病，如癌症。
• Anti-Markovnikov hydroamination and hydrothiolation of electron-deficient vinylarenes catalyzed by well-defined monomeric copper(<scp>i</scp>) amido and thiolate complexes
  作者：Colleen Munro-Leighton、Samuel A. Delp、Nikki M. Alsop、Elizabeth D. Blue、T. Brent Gunnoe

  DOI：10.1039/b715507g

  日期：——

  thiolate complexes that are supported by the N-heterocyclic carbene ligand 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (IPr) catalyze the hydroamination and hydrothiolation of electron-deficient vinylarenes with reactivity patterns that are consistent with an intermolecular nucleophilic addition of the amido/thiolate ligand of (IPr)Cu(XR) (X = NH or S; R = Ph, CH2Ph) to free vinylarene.

  N-杂环卡宾配体1,3-双（2,6-二异丙基苯基）咪唑-2-亚烷基（IPr）负载的单体Cu（I）酰胺和硫醇盐配合物催化缺电子乙烯基芳烃的加氢胺化和氢硫醇化与（IPr）Cu（XR）的酰胺/硫醇盐配体的分子间亲核加成（X = NH或S; R = Ph，CH2Ph）到游离乙烯基芳烃的反应模式。
• Synthesis and Evaluation of Novel Phenylethanolamine Derivatives containing Acetanilides as Potent and Selective .BETA.3-Adrenergic Receptor Agonists
  作者：Tatsuya Maruyama、Kenichi Onda、Masahiko Hayakawa、Takayuki Suzuki、Tetsuya Kimizuka、Tetsuo Matsui、Toshiyuki Takasu、Itsuro Nagase、Noritaka Hamada、Mitsuaki Ohta

  DOI：10.1248/cpb.58.533

  日期：——

  In the search for potent and selective human β3-adrenergic receptor (AR) agonists as potential pharmacotherapies for the treatment of obesity and non-insulin dependent (type II) diabetes, we prepared a novel series of phenylethanolamine derivatives containing acetanilides and evaluated their biological activities at the human β3-, β2-, and β1-ARs. Among these compounds, the 6-amino-2-pyridylacetanilide (36b), 2-amino-5-methylthiazol-4-ylacetanilide (36g), and 5-amino-1,2,4-thiadiazol-3-ylacetanilide (36h) derivatives showed potent agonistic activity at the β3-AR with functional selectivity over the β1- and β2-ARs. In addition, these compounds exhibited significant hypoglycemic activity in a rodent diabetic model.

  在寻找有效且选择性的人类β3-肾上腺素受体（AR）激动剂作为治疗肥胖和非胰岛素依赖型（2型）糖尿病的潜在药物治疗时，我们准备了一系列新颖的含有醋酸酰胺的苯乙醇胺衍生物，并评估了它们在人体β3-、β2-和β1-AR上的生物活性。在这些化合物中，6-氨基-2-吡啶基醋酸酰胺（36b）、2-氨基-5-甲基噻唑-4-基醋酸酰胺（36g）和5-氨基-1,2,4-噻二唑-3-基醋酸酰胺（36h）衍生物在β3-AR上显示出强烈的激动活性，并且对β1-和β2-AR具有功能选择性。此外，这些化合物在啮齿动物糖尿病模型中还表现出显著的降血糖活性。
• Amide derivatives or salts thereof
  申请人：Yamanouchi Pharmaceutical Co., Ltd.

  公开号：US06346532B1

  公开（公告）日：2002-02-12

  Amide derivatives represented by general formula (I) or salts thereof wherein each symbol has the following meaning: ring B: an optionally substituted heteroaryl optionally fused with a benzene ring; X: a bond, lower alkylene or lower alkenylene optionally substituted by hydroxy or lower alkyl, carbonyl, or a group represented by —NH— (when X is lower alkylene optionally substituted by lower alkyl which may be bonded to the hydrogen atom bonded to a constituent carbon atom of ring B to form lower alkylene to thereby form a ring); A: a lower alkylene or a group represented by -(lower alkylene)—O—; R1a and R1b: the same or different and each hydrogen or lower alkyl; R2: hydrogen or halogeno; and Z: nitrogen or a group represented by ═CH—. The compounds are useful as a diabetes remedy which not only functions to both accelerate the secretion of insulin and enhance insulin sensitivity but has an antiobestic action and an antihyperlipemic action based on its selective stimulative action on a &bgr;3 receptor.

  通用公式（I）表示的酰胺衍生物或其盐，其中每个符号的含义如下：环B：可选地取代的杂环芳基，可选地与苯环融合；X：键，较低的烷基或烯基，可选地取代为羟基或较低的烷基，酰基，或由—NH—表示的基团（当X为较低的烷基时，可选地取代为较低的烷基，可能与环B上的一个碳原子上的氢原子结合以形成较低的烷基从而形成一个环）；A：较低的烷基或由-(较低的烷基)—O—表示的基团；R1a和R1b：相同或不同，各为氢或较低的烷基；R2：氢或卤素；Z：氮或由═CH—表示的基团。这些化合物可用作糖尿病疗法，不仅能加速胰岛素的分泌和增强胰岛素敏感性，还具有抗肥胖作用和抗高脂血症作用，这是基于其对β3受体的选择性刺激作用。