N-乙基-4-甲氧基-2-硝基苯胺 | 3360-85-8

• 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: N-乙基-4-甲氧基-2-硝基苯胺
• 英文名称: N-ethyl-(4-methoxy-2-nitrophenyl)amine
• 英文别名: N-ethyl-2-nitro-4-methoxyaniline；N-ethyl-4-methoxy-2-nitro-aniline；N-Aethyl-4-methoxy-2-nitro-anilin；N-ethyl-4-methoxy-2-nitroaniline
• CAS: 3360-85-8
• 化学式: C₉H₁₂N₂O₃
• mdl: MFCD00464056
• 分子量: 196.206
• InChiKey: HXGAXPKXJXONSA-UHFFFAOYSA-N

物化性质

• 熔点：
  59-60 °C
• 沸点：
  344.1±32.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  67.1
• 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：

  N-乙基-4-甲氧基-2-硝基苯胺 在 盐酸 、 tin 作用下， 生成 (9ci)-1-乙基-5-甲氧基-1H-苯并咪唑
  参考文献：
  名称：

  Witkewitsch; Simonow, Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2614,2616; engl. Ausg. S. 2578, 2580

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(4-甲氧基-2-硝基苯)苯磺酰胺 在 硫酸 作用下， 生成 N-乙基-4-甲氧基-2-硝基苯胺
  参考文献：
  名称：

  Witkewitsch; Simonow, Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2614,2616; engl. Ausg. S. 2578, 2580

  摘要：

  DOI：

文献信息

• Bent Tridentate Receptors in Calamitic Mesophases with Predetermined Photophysical Properties:  New Luminescent Lanthanide-Containing Materials
  作者：Homayoun Nozary、Claude Piguet、Paul Tissot、Gérald Bernardinelli、Jean-Claude G. Bünzli、Robert Deschenaux、Daniel Guillon

  DOI：10.1021/ja982545n

  日期：1998.12.1

  6-bis(benzimidazol-2‘-yl)pyridine cores into rodlike ligands L11-17. The crystal structure of the nonmesogenic ligand L13 (C39H37N5O4, triclinic, P1, Z = 2) shows the expected trans−trans conformation of the tridentate binding unit, which provides a linear arrangement of the semirigid aromatic sidearms. The crystal structure of the related mesogenic ligand L16 (C61H81N5O4, triclinic, P1, Z = 2) demonstrates

  已开发出一种新的合成策略，将弯曲且刚性的三齿 2,6-双（苯并咪唑-2'-基）吡啶核引入棒状配体 L11-17。非介晶配体 L13（C39H37N5O4，三斜，P1，Z = 2）的晶体结构显示了三齿结合单元的预期反式-反式构象，它提供了半刚性芳香侧臂的线性排列。相关介晶配体 L16（C61H81N5O4，三斜，P1，Z = 2）的晶体结构表明亲脂侧链采用完全延伸的构象，导致略微螺旋扭曲的 I 形分子。通过明智地选择刚性中心核和半刚性亲脂性侧臂之间的间隔物，可以产生丰富多样的介晶现象，可以与电子和光物理特性的同时调整相结合。配体 L13,14 与 Ln(NO3)3·xH2O 反应以定量和选择性地生成中性 1:1 配合物 [Ln(Li)( )3] (Ln = La to Lu)，它们稳定...
• Metallo-Responsive Liquid Crystalline Monomers and Polymers
  作者：Blayne M. McKenzie、Rudy J. Wojtecki、Kelly A. Burke、Cuiyu Zhang、Antal Jákli、Patrick T. Mather、Stuart J. Rowan

  DOI：10.1021/cm2011617

  日期：2011.8.9

  transitions and phases. The binding of lanthanide- and/or transition metal salts to the ligand containing mesogens results in a transition from a liquid crystalline to an isotropic state. Acyclic diene metathesis of the monomers yielded either oligomers or polymers, dictated by whether the alkene is either terminal or nonterminal, respectively. Both oligomers and polymers exhibit enantiotropic liquid crystalline

  已经制备和研究了一系列具有化学响应特性的含液晶配体的单体。这些分子是2，6-双苯并咪唑基吡啶（Bip）配体的功能化衍生物。调整芳族核的尺寸和两对烷基取代基的长度可以制备具有一系列可调节的热液晶转变和相的介晶。镧系元素和/或过渡金属盐与含配体的液晶元的结合导致从液晶态到各向同性态的转变。单体的无环二烯复分解生成低聚物或聚合物，这分别取决于烯烃是末端还是非末端。
• Toward lanthanide-containing metallomesogens with tridentate ligands
  作者：Homayoun Nozary、Claude Piguet、Paul Tissot、Homayoun Nozary、Gérald Bernardinelli、Claude Piguet、Paul Tissot、Robert Deschenaux、Maria-Teresa Vilches

  DOI：10.1039/a705776h

  日期：——

  Tridentate aromatic receptors L1–L4 containing the 2,6-bis(benzimidazol-2-yl)pyridine chelating unit are designed to exhibit thermotropic calamitic liquid-crystalline phases; the mesomorphic behaviour is essentially retained in the complex [LuL2(NO3)3].

  含有 2,6-双（苯并咪唑-2-基）吡啶螯合单元的三叉芳香族受体 L1-L4 被设计成具有热致性的钙镁液晶相；[LuL2(NO3)3] 复合物基本上保留了介形行为。
• Improved synthesis of functionalized mesogenic 2,6-bisbenzimidazolylpyridine ligands
  作者：Blayne M. McKenzie、Adriane K. Miller、Rudy J. Wojtecki、J. Casey Johnson、Kelly A. Burke、Karis A. Tzeng、Patrick T. Mather、Stuart J. Rowan

  DOI：10.1016/j.tet.2008.05.075

  日期：2008.9

  while facilitating scale up to multi-gram quantities in good yields (63–90%). The previous synthetic methodology was improved through judicious choice of the reducing agent and solvent in the reduction/ring-closing step. Via this platform, we also successfully accessed a mesogenic Bip ligand and herein report initial liquid crystalline properties of this derivative.

  提供了一种通用的一锅合成平台，用于制备一系列功能化的2,6-双苯​​并咪唑基吡啶（Bip）衍生物。该协议可显着降低以前的合成路线的成本和时间，同时有助于以良好的收率（63–90％）扩大至多克数量。通过在还原/闭环步骤中明智地选择还原剂和溶剂，改进了先前的合成方法。通过该平台，我们还成功访问了介晶Bip配体，并在此报告了该衍生物的初始液晶性质。
• Development of a Selective Inhibitor of Protein Arginine Deiminase 2
  作者：Aaron Muth、Venkataraman Subramanian、Edward Beaumont、Mitesh Nagar、Philip Kerry、Paul McEwan、Hema Srinath、Kathleen Clancy、Sangram Parelkar、Paul R. Thompson

  DOI：10.1021/acs.jmedchem.7b00274

  日期：2017.4.13

  Protein arginine deiminase 2 (PAD2) plays a key role in the onset and progression of multiple sclerosis, rheumatoid arthritis, and breast cancer. To date, no PAD2-selective inhibitor has been developed. Such a compound will be critical for elucidating the biological roles of this isozyme and may ultimately be useful for treating specific diseases in which PAD2 activity is dysregulated. To achieve this goal, we synthesized a series of benzimidazole-based derivatives of Cl-amidine, hypothesizing that this scaffold would allow access to a series of PAD2-selective inhibitors with enhanced cellular efficacy. Herein, we demonstrate that substitutions at both the N-terminus and C-terminus of Cl-amidine result in >100-fold increases in PAD2 potency and selectivity (30a, 41a, and 49a) as well as cellular efficacy (30a). Notably, these compounds use the far less reactive fluoroacetamidine warhead. In total, we predict that 30a will be a critical tool for understanding cellular PAD2 function and sets the stage for treating diseases in which PAD2 activity is dysregulated.