4-(甲基(苯基)氨基)丁酸乙酯 | 38113-78-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 4-(甲基(苯基)氨基)丁酸乙酯
• 英文名称: ethyl 4-(methyl(phenyl)amino)butanoate
• 英文别名: ethyl 4-(N-methylanilino)butanoate
• CAS: 38113-78-9
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: MMNYLRPQFIUOFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  320.5±25.0 °C(Predicted)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(甲基(苯基)氨基)丁酸乙酯 在 potassium hydroxide 作用下， 反应 2.0h， 以98%的产率得到4-(methyl(phenyl)amino)butanoic acid
  参考文献：
  名称：

  超声刺激成核和染料组装成扩展的凝胶纳米结构的生长。

  摘要：

  已合成并充分表征了一种方丁酸染料，该方酸染料通过能够自组装的柔性二酰胺键（GA-SQ）与庞大的三烷氧基苯基部分官能化。将GA‐SQ的热溶液快速冷却至0°C会导致自组装沉淀物，该沉淀物由两种类型的纳米结构组成：环和不确定的短纤维。超声的应用改变了过饱和介导的成核条件，仅产生一种核，并促进了晶体纤维结构的形成，诱导了溶剂分子的凝胶化。GA-SQ的独特自组装行为在超声刺激下，已经通过吸收，发射，FT-IR，XRD，SEM，AFM和TEM技术进行了详细研究。这些研究揭示了自组装材料的成核生长机制，这在超声诱导胶凝领域很少受到关注。此外，为了探究纳米级基质对超声诱导的自组装的影响，添加了微量的单壁碳纳米管，从而通过异质成核过程加速了自组装，最终提供了具有纳米带状形态的超分子凝胶。这项研究表明，功能性染料的自组装可以通过外部刺激来明智地操纵，并且可以通过添加碳纳米管来进一步控制。

  DOI：

  10.1002/chem.201301539
• 作为产物：
  描述：

  N-Boc-苯胺 在 sodium hydride 、 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 4-(甲基(苯基)氨基)丁酸乙酯
  参考文献：
  名称：

  Identification of 5-Substituted 2-Acylaminothiazoles That Activate Tat-Mediated Transcription in HIV-1 Latency Models

  摘要：

  The persistent reservoir of cells latently infected with human immunodeficiency virus (HIV)-integrated proviral DNA necessitates lifelong suppressive antiretroviral therapy (ART). Epigenetic targeted compounds have shown promise as potential latency-reversing agents; however, these drugs have undesirable toxicity and lack specificity for HIV. We utilized a novel HEK293-derived FlpIn dual-reporter cell line, which quantifies specific HIV provirus reactivation (LTR promoter) relative to nonspecific host cell gene expression (CMV promoter), to identify the 5-substituted 2-acylaminothiazole hit class. Here, we describe the optimization of the hit class, defining the functionality necessary for HIV gene activation and for improving in vitro metabolism and solubility. The optimized compounds displayed enhanced HIV gene expression in HEK293 and Jurkat 10.6 latency cellular models and increased unspliced HIV RNA in resting CD4+ T cells isolated from HIV-infected individuals on ART, demonstrating the potential of the 2-acylaminothiazole class as latency-reversing agents.

  DOI：

  10.1021/acs.jmedchem.9b00462

文献信息

• Efficient Unimolecular Deprotonation of Aniline Radical Cations
  作者：Gary W. Dombrowski、Joseph P. Dinnocenzo、Paul A. Zielinski、Samir Farid、Zofia M. Wosinska、Ian R. Gould

  DOI：10.1021/jo047813g

  日期：2005.5.1

  deprotonation as a function of aniline radical cation pKa (Brønsted plots) demonstrate that the effect is not simply due to a change in the reaction thermodynamics. By combining this stereoelectronic effect with covalent attachment of carboxylate as a base, aniline radical cations that undergo unimolecular deprotonation with rate constants as high as 108 s-1, even in unfavorable protic media, are described

  芳香胺（例如苯胺）的自由基阳离子的去质子化通常比其他裂解反应要慢得多。在这里，我们报告了一种立体电子效应，其中涉及苯胺基团从苯环平面外的扭曲，从而导致去质子化的反应率显着提高。对去质子化速率常数作为苯胺自由基阳离子p K a的函数的定量研究（布朗斯台德图）表明，这种作用不仅仅是由于反应热力学的变化。通过将这种立体电子效应与羧酸盐作为碱的共价结合起来，苯胺自由基阳离子经历了非分子去质子化，速率常数高达10 8 s - 1描述了即使在不利的质子介质中也是如此。
• Dual Benzophenone/Copper‐Photocatalyzed Giese‐Type Alkylation of C(sp ³ )−H Bonds
  作者：Baptiste Abadie、Damien Jardel、Gianluca Pozzi、Patrick Toullec、Jean‐Marc Vincent

  DOI：10.1002/chem.201904111

  日期：2019.12.13

  benzophenone (BP) with a catalytic amount of Cu(OAc)2 . Under mild and operationally simple conditions, the Giese adducts resulting from the C(sp3 )-H functionalization of amines, alcohols, ethers, and cycloalkanes could be synthesized. Preliminary mechanistic studies have revealed that the reaction does not proceed through a radical chain, but through a dual BP/Cu photocatalytic process, in which both CuII

  C(sp3 )-H 键的光催化 Giese 型烷基化在 CC 键形成的原子经济背景下是非常有吸引力的反应。这种反应的主要限制是，当使用高度可聚合的烯烃受体，如未取代的丙烯酸酯、丙烯腈或甲基乙烯基酮时，自由基聚合通常成为主要或排他的反应途径。在此，我们报告说，当将二苯甲酮 (BP) 的光催化活性与催化量的 Cu(OAc)2 结合时，此类烯烃的聚合受到强烈限制或抑制。在温和且操作简单的条件下，可以合成由胺、醇、醚和环烷烃的 C(sp3 )-H 官能化产生的 Giese 加合物。
• Alkylation of the α-amino C–H bonds of anilines photocatalyzed by a DMEDA-Cu-benzophenone complex: reaction scope and mechanistic studies
  作者：Baptiste Abadie、Gediminas Jonusauskas、Nathan D. McClenaghan、Patrick Y. Toullec、Jean-Marc Vincent

  DOI：10.1039/d1ob00960e

  日期：——

  complex 1 incorporating a BP chromophore is a highly active and chemoselective photocatalyst for the alkylation of α-amino C–H bonds of anilines. The reaction was shown to proceed with a broad substrate scope in the absence of additives. Extensive mechanistic studies were performed, in particular using transient absorption spectroscopy, and spectroscopic signatures of key intermediates were identified

  含有 BP 发色团的 Cu( II )配合物1是一种高活性和化学选择性的光催化剂，用于苯胺的 α-氨基 C-H 键的烷基化。该反应显示在没有添加剂的情况下以广泛的底物范围进行。进行了广泛的机理研究，特别是使用瞬态吸收光谱，并在催化条件下确定了关键中间体的光谱特征。最后，通过一锅法进行多组分 CuAAC 和烯烃加氢烷基化反应，展示了1作为多任务催化剂的能力。
• The Coupling of Tertiary Amines with Acrylate Derivatives via Visible-Light Photoredox Catalysis
  作者：Xiaojun Dai、Dongping Cheng、Baochuan Guan、Wenjuan Mao、Xiaoliang Xu、Xiaonian Li

  DOI：10.1021/jo501097b

  日期：2014.8.1

  Catalyzed by Ru(bpy)3(BF4)2, the photoredox coupling of tertiary amines with acrylate derivatives including Baylis–Hillman adducts under visible light irradiation was successfully established. The scope of the substrates was broad, and thus an array of γ-aminobutyric ester derivatives was obtained in moderate to good yields.

  通过Ru（bpy）3（BF 4）2催化，成功建立了叔胺与丙烯酸酯衍生物（包括Baylis-Hillman加合物）在可见光下的光氧化还原偶联。底物的范围很广，因此以中等至良好的产率获得了一系列的γ-氨基丁酸酯衍生物。
• Molecular Tuning of Styryl Dyes Leads to Versatile and Efficient Plasma Membrane Probes for Cell and Tissue Imaging
  作者：Mayeul Collot、Emmanuel Boutant、Kyong Tkhe Fam、Lydia Danglot、Andrey S. Klymchenko

  DOI：10.1021/acs.bioconjchem.0c00023

  日期：2020.3.18

  The plasma membrane (PM) plays a major role in many biological processes; therefore, its proper fluorescence staining is required in bioimaging. Among the commercially available PM probes, styryl dye FM1-43 is one of the most widely used. In this work, we demonstrated that fine chemical modifications of FM1-43 can dramatically improve the PM staining. The newly developed probes, SP-468 and SQ-535, were found to display enhanced photophysical properties (reduced cross-talk, higher brightness, improved photostability) and, unlike FM1-43, provided excellent and immediate PM staining in 5 different mammalian cell types including neurons (primary culture and tissue imaging). Taking advantage of these features, we successfully used SP-468 in STED super resolution neuronal imaging. Additionally, we showed that the new probes displayed differences in their internalization pathways compared to their parent FM1-43. Finally, we showed that the new probes kept the ability to stain the PM of plant cells. Overall, this work presents new useful probes for PM imaging in cells and tissues and provides insights on the molecular design of new PM targeting molecules.

  质膜（PM）在许多生物过程中发挥着重要作用，因此在生物成像中需要对其进行适当的荧光染色。在市售的质膜探针中，苯乙烯基染料 FM1-43 是应用最广泛的探针之一。在这项工作中，我们证明了对 FM1-43 进行精细化学修饰可显著改善 PM 染色效果。与 FM1-43 不同，新开发的探针 SP-468 和 SQ-535 显示出更强的光物理特性（减少串扰、提高亮度、改善光稳定性），并能在包括神经元在内的 5 种不同哺乳动物细胞类型（原代培养和组织成像）中提供出色的即时 PM 染色。利用这些特点，我们成功地将 SP-468 用于 STED 超分辨率神经元成像。此外，我们还发现，与母体 FM1-43 相比，新探针的内化途径有所不同。最后，我们还发现新探针保持了对植物细胞PM染色的能力。总之，这项工作为细胞和组织中的 PM 成像提供了新的有用探针，并为新的 PM 靶向分子的分子设计提供了启示。