2-(4-溴苯基氨基)乙烷-1-醇 | 55110-99-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-(4-溴苯基氨基)乙烷-1-醇
• 英文名称: 2-(4-bromophenylamino)ethanol
• 英文别名: 2-((4-bromophenyl)amino)ethan-1-ol；2-[(4-Bromophenyl)amino]ethan-1-ol；2-(4-bromoanilino)ethanol
• CAS: 55110-99-1
• 化学式: C₈H₁₀BrNO
• mdl: MFCD11153144
• 分子量: 216.077
• InChiKey: GYWMAZOWKOVMKS-UHFFFAOYSA-N

物化性质

• 熔点：
  93 °C
• 沸点：
  337.9±22.0 °C(Predicted)
• 密度：
  1.553±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 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：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-溴苯基氨基)乙烷-1-醇 在 盐酸 作用下， 生成 [3-(4-bromo-phenyl)-thiazolidin-2-ylidene]-[1]naphthyl-amine
  参考文献：
  名称：

  Dains et al., Journal of the American Chemical Society, 1925, vol. 47, p. 1983

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(4-溴苯基亚氨基)乙酸-(E)-乙酯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 2-(4-溴苯基氨基)乙烷-1-醇
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Urea Derivatives as Highly Potent and Selective Rho Kinase Inhibitors

  摘要：

  RhoA and its downstream effector ROCK mediate stress fiber formation and cell contraction through their effects on the phosphorylation of myosin light chain (MLC). Inhibition of the RhoA/ROCK pathway has proven to be a promising strategy for several indications such as cardiovascular disease, glaucoma, and inflammatory disease. In 2010, our group reported urea-based ROCK inhibitors as potential antiglaucoma agents. These compounds showed potent IC50 values in enzymatic and cell-based assays and significant intraocular pressure (IOP)-lowering effects in rats (similar to 7 mmHg).(22) To develop more advanced ROCK inhibitors targeting various potential applications (such as myocardial infarction, erectile dysfunction, multiple sclerosis, etc.) in addition to glaucoma, a thorough SAR for this urea-based scaffold was studied. The detailed optimization process, counter-screening, and in vitro and in vivo DMPK studies are discussed. Potent and selective ROCK inhibitors with various in vivo pharmacokinetic properties were discovered.

  DOI：

  10.1021/jm400062r

文献信息

• <i>N</i>-Arylazetidines: Preparation through Anionic Ring Closure
  作者：Pierre Quinodoz、Bruno Drouillat、Karen Wright、Jérôme Marrot、François Couty

  DOI：10.1021/acs.joc.6b00169

  日期：2016.4.1

  substituted N-aryl-2-cyanoazetidines based on an anionic ring-closure reaction. These compounds can be prepared from β-amino alcohols in enantiomerically pure form through a three-step sequence involving (i) copper-catalyzed N-arylation, (ii) N-cyanomethylation of the secondary aniline, and (iii) one-pot mesylation followed by ring closure induced by a base. This high-yielding sequence gives access to azetidines

  我们在此报告了基于阴离子闭环反应的有效合成的各种取代的N-芳基-2-氰基氮杂环丁烷。这些化合物可以由对映体纯形式的β-氨基醇通过三步法制备，其中包括（i）铜催化的N-芳基化，（ii）N-仲苯胺的-氰基甲基化，和（iii）一锅甲磺酸化，然后由碱基诱导的闭环。这种高产率的序列使得可以以可预测的和可调节的取代模式以及可预测的非对映选择性接近氮杂环丁烷。这些化合物易于通过铃木偶联或腈转化进行多次进一步衍生化，因此显示为用于药物化学的有价值的新支架。通过AM1计算和X射线晶体学分析揭示了它们的刚性形状，具有几乎平面的N-芳基胺和平面的四元环。
• Thiazolinone unsubstituted quinolines
  申请人：Chen Li

  公开号：US20060004045A1

  公开（公告）日：2006-01-05

  Thiazolinone quinoline derivatives having no substitution on the quinoline ring active as CDK1 inhibitors which are useful as anti-proliferation agents such as for treating solid tumors.

  噻唑酮喹啉衍生物在喹啉环上没有取代基，作为CDK1抑制剂活性，可用作抗增殖剂，例如用于治疗实体肿瘤。
• Room-Temperature Practical Copper-Catalyzed Amination of Aryl Iodides
  作者：Christopher Deldaele、Gwilherm Evano

  DOI：10.1002/cctc.201501375

  日期：2016.4.6

  An efficient and highly practical procedure is reported for the Ullmann–Goldberg‐type copper‐catalyzed amination of aryl iodides. By using a combination of copper iodide and proline in the presence of an excess of an amine, a wide range of aryl iodides can be readily aminated at room temperature. The reaction proceeds well regardless of the electronic properties of the starting aryl iodide and the

  据报道，Ullmann–Goldberg型铜催化芳基碘化物的胺化反应是一种有效且高度实用的程序。通过在过量胺的存在下使用碘化铜和脯氨酸的组合，可以在室温下容易地胺化各种各样的芳基碘。无论起始碘代芳基化物的电子性质如何，反应都进行得很好，并且在大多数情况下不需要通过柱色谱法纯化就可以得到胺化产物。由于其效率和反应条件的温和性，该胺化反应还可扩展至在室温下胺化复杂的芳基碘化物。
• The Acrylamide Moiety as an Activated Alkene Component in the Intramolecular Baylis-Hillman Reaction: Facile Synthesis of Functionalized α-Methylene Lactam and Spirolactam Frameworks
  作者：Deevi Basavaiah、Guddeti Chandrashekar Reddy、Kishor Chandra Bharadwaj

  DOI：10.1002/ejoc.201301526

  日期：2014.2

  A facile strategy for the intramolecular Baylis–Hillman reaction by utilizing an acrylamide moiety as an activated alkene component was developed, which thus provides a convenient protocol for obtaining five- and six-membered α-methylene lactam and spirolactam derivatives.

  开发了一种利用丙烯酰胺部分作为活化烯烃组分进行分子内 Baylis-Hillman 反应的简便策略，从而为获得五元和六元 α-亚甲基内酰胺和螺内酰胺衍生物提供了方便的方案。
• Chemoselective<i>O</i>-formyl and<i>O</i>-acyl protection of alkanolamines, phenoxyethanols and alcohols catalyzed by nickel(<scp>ii</scp>) and copper(<scp>ii</scp>)-catalysts
  作者：Rahul B. Sonawane、Swapnali R. Sonawane、Nishant K. Rasal、Sangeeta V. Jagtap

  DOI：10.1039/d0gc00520g

  日期：——

  alkanolamines, that have both amines and alcohols as reactive functional groups. Achieving 100% selectivity for O-formyl and O-acyl protection of alkanolamines is one of the examples of such reactions. To avoid protection and deprotection steps and overcome this problem, a novel chemoselective, efficient, and simple protocol for functional group protection as O-formylation and O-acylation of alkanolamines and

  对于具有胺和醇作为反应性官能团的双官能化合物（例如烷醇胺），实现化学选择性始终是至关重要且具有挑战性的。这种反应的例子之一是使烷醇胺的O-甲酰基和O-酰基保护的选择性达到100％。为避免保护和脱保护步骤并克服这一问题，Ni（Ni（Ni））催化了一种新的化学选择性，有效且简单的官能团保护方案，如烷醇胺和苯氧基乙醇的O-甲酰化和O-酰化以及醇和胺之间的竞争性O-选择性。II）和Cu（II）在均相介质中仅以5 mol％的催化剂负载量与8-羟基喹啉形成络合物。在不存在用于室温下以甲酸为甲酰基源的O-甲酰化溶剂和在70°C下以乙酸为酰基源的O-酰化条件下，可获得良好或优异的收率。另外，在该反应过程中产生最少的废水和废物，因为相应的酸的钠盐可以在该过程中回收并可以重复使用。这种化学反应容易耐受各种官能团，如20个对烷醇胺的O-甲酰化和O-酰化具有100％化学选择性的实例以及30个O-甲酰化和在已成功合