N-(3-formylphenyl)acetamide | 123306-28-5

• 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-(3-formylphenyl)acetamide
• 英文别名: 3-acetylaminobenzylacetate；1-acetoxymethyl-3-acetylamino-benzene；1-Acetoxymethyl-3-acetylamino-benzol；3-Acetamino-α-acetoxy-toluol；(3-Acetamino-benzyl)-acetat；3-acetoxymethylacetanilide；3-Acetamidobenzyl acetate；(3-acetamidophenyl)methyl acetate
• CAS: 123306-28-5
• 化学式: C₁₁H₁₃NO₃
• mdl: MFCD14156078
• 分子量: 207.229
• InChiKey: QBUNQFCOHXQKQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-formylphenyl)acetamide 在 盐酸 、 硝酸 作用下， 生成 3-(羟基甲基)-4-硝基苯胺
  参考文献：
  名称：

  Fourneau; de Lestrange, Bulletin de la Societe Chimique de France, 1933, vol. <4> 53, p. 330,332

  摘要：

  DOI：
• 作为产物：
  描述：

  3-硝基苯甲醇 在 铁粉 、 氯化铵 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 N-(3-formylphenyl)acetamide
  参考文献：
  名称：

  Validation of PqsD as an Anti-biofilm Target in Pseudomonas aeruginosa by Development of Small-Molecule Inhibitors

  摘要：

  2-Hepty1-4-hydroxyquinoline (HHQ) and Pseudomonas quinolone signal (PQS) are involved in the regulation of virulence factor production and biofilm formation in Pseudomonas aeruginosa. PqsD is a key enzyme in the biosynthesis of these signal molecules. Using a ligand-based approach, we have identified the first class of PqsD inhibitors. Simplification and rigidization led to fragments with high ligand efficiencies. These small molecules repress HHQ and PQS production and biofilm formation in P. aeruginosa. This validates PqsD as a target for the development of anti-infectives.

  DOI：

  10.1021/ja3072397

文献信息

• Practical Chemoselective Acylation: Organocatalytic Chemodivergent Esterification and Amidation of Amino Alcohols with <i>N</i> ‐Carbonylimidazoles
  作者：Hope Nelson、William Richard、Hailee Brown、Abigail Medlin、Christina Light、Stephen T. Heller

  DOI：10.1002/anie.202107438

  日期：2021.10.11

  DBU-catalyzed esterification: A single esterification product was obtained from a molecule containing primary aniline, alcohol, phenol, secondary amide, and N−H indole groups. These acylation reactions are highly practical as they involve only readily available, inexpensive, and relatively safe reagents; can be performed on a multigram scale; and can be used on carboxylic acids directly by in situ formation

  化学选择性转化是高效有机合成的基石；然而，即使是简单的转化，如酰化反应，要实现这一目标也常常是一个挑战。我们报告说，N-羰基咪唑分别在吡啶鎓离子或 1,8-二氮杂双环 [5.4.0] undec-7-ene (DBU) 存在下能够催化化学发散的苯胺或醇酰化。两种酰化反应都显示出对目标基团的高而广泛的化学选择性。在 DBU 催化的酯化中观察到了前所未有的化学选择性水平：从含有伯苯胺、醇、苯酚、仲酰胺和N的分子中获得单一酯化产物-H吲哚基团。这些酰化反应非常实用，因为它们只涉及容易获得、便宜且相对安全的试剂；可以在多克规模上进行；并且可以通过原位形成酰基咪唑亲电试剂直接用于羧酸。
• Substituted 2-nitrobenzyltrichloroacetate esters for photodirected oligonucleotide detritylation in solid films
  作者：Pawel J. Serafinowski、Peter B. Garland

  DOI：10.1039/b806902f

  日期：——

  Oligonucleotide microarray fabrication by chemical synthesis using photoacid generators in solid films could have advantages over existing methods, but has not matched the accuracy of conventional synthesis where detritylation is performed with acid solutions. To address this problem, we explored the kinetics and equilibria of nucleoside detritylation in solid films, using trichloroacetic acid (TCA)

  通过使用固态膜中的光致产酸剂进行化学合成的寡核苷酸微阵列制造可能具有优于现有方法的优势，但与以酸溶液进行去三苯甲基化的常规合成方法的准确性不匹配。为了解决这个问题，我们使用由三氯乙酸（TCA）从其酯与取代的2-硝基苄基醇进行光解生成的三氯乙酸（TCA），探索了固体膜中核苷去三苯甲基化的动力学和平衡。我们合成了25种被所有α-苯基取代的酯，并评估了它们作为固体膜光致产酸剂的潜力。它们包括在（2-i-硝基）中具有（i）单或二甲氧基或（ii）5-卤代，（iii）烷基或芳基取代的5-氨基或（iv）5-芳基取代基的组。或2，6-二硝基苄基环。其紫外线光谱的最大吸收范围为230至410 nm，在365 nm处的量子产率从<0.01到接近1.0。所述酯在载玻片上形成光学透明的固体膜，而没有添加聚合物。膜内光酸生成，质子活性变化和去三苯甲基化的动力学进行了现场测量。对光敏感性和去三苯甲基化最有效的酯是5-氯-，5-溴-，4
• Ni2B@Cu2O and Ni2B@CuCl2: two new simple and efficient nanocatalysts for the green one-pot reductive acetylation of nitroarenes and direct N-acetylation of arylamines using solvent-free mechanochemical grinding
  作者：Behzad Zeynizadeh、Reza Younesi、Hossein Mousavi

  DOI：10.1007/s11164-018-3559-x

  日期：2018.12

  Abstract Ni2B@Cu2O and Ni2B@CuCl2 are introduced as simple and efficient earth-abundant transition-metal-based nanocomposites for the green one-pot reductive acetylation of aromatic nitro compounds and direct N-acetylation of arylamines using a solvent-free mechanochemical grinding technique. The designed Ni2B-based nanocomposites were characterized by Fourier-transform infrared (FT-IR) spectroscopy

  摘要 引入Ni 2 B @ Cu 2 O和Ni 2 B @ CuCl 2作为简单有效的基于稀土的过渡金属基纳米复合材料，用于芳族硝基化合物的绿色一锅还原乙酰化和使用N的芳基胺的直接N-乙酰化。无溶剂机械化学研磨技术。设计的Ni 2B基纳米复合材料的特征在于傅立叶变换红外（FT-IR）光谱，X射线衍射（XRD）分析和具有能量色散X射线（EDX）的扫描电子显微镜（SEM）。这些方法的显着优势包括：广泛的底物范围，使用无溶剂的机械化学研磨技术，以简单实用的催化剂实现富含土类的过渡金属基纳米复合材料，以及在环境条件下反应时间短且产率高。所提及的方法也可以成功地用于使用绿色化学方法合成多种其他酰胺（尤其是取代的乙酰胺）的方法。此外，还研究了上述新型纳米复合材料的可回收性和可重复使用性。 图形概要
• .gamma.-L-glutamyl-4-nitroanilide derivatives and process for
  申请人：Wako Pure Chemical Industries, Ltd.

  公开号：US04851572A1

  公开（公告）日：1989-07-25

  A .gamma.-L-glutamyl-4-nitroanilide derivative of the formula: ##STR1## wherein R is a lower hydroxyalkyl group, is suitable as a substrate for determining .gamma.-GTP activity.

  公式为：##STR1## 其中R为较低的羟基烷基，是用于测定.gamma.-GTP活性的底物的.gamma.-L-谷氨酰-4-硝基苯胺衍生物。
• The immobilized Cu nanoparticles on magnetic montmorillonite (MMT@Fe3O4@Cu): As an efficient and reusable nanocatalyst for reduction and reductive-acetylation of nitroarenes with NaBH4
  作者：Behzad Zeynizadeh、Soleiman Rahmani、Hengameh Tizhoush

  DOI：10.1016/j.poly.2019.114201

  日期：2020.1

  In this study, the immobilization of copper nanoparticles on superparamagnetic montmorillonite, MMT@Fe3O4@Cu, was studied. Magnetically nanoparticles (MNPs) of iron oxide (Fe3(O)4) were primarily prepared by a chemical co-precipitation method. Next, the prepared Fe3O4 MNPs were intercalated within the interlamellar spaces and external surface of sodium-exchanged montmorillonite. Finally, Cu NPs were immobilized on magnetic montmorillonite by a simply mixing of an aqueous solution of CuCl2.2H(2)O with MMT@Fe3O4 followed by the reduction with NaBH4. Characterization of MMT@Fe3O4 clay system represented that through the immobilization of Fe3O4 MNPs, disordered-layers structure of MMT was easily reorganized to an ordered-layers arrangement. The synthesized composite systems were characterized using FT-IR, SEM, EDX, XRD, VSM, BET and ICP-OES analyses. SEM analysis exhibited that dispersion of Cu NPs, with the size distribution of 15-25 nm, on the surface of magnetic clay was taken place perfectly. BET surface analysis indicated that after the immobilization of Fe3O4 and Cu species, the surface area and total pore volume of MMT@Fe3O4@Cu system was decreased. Next, the Cu-clay nanocomposite system showed a perfect catalytic activity towards reduction of nitroarenes to anilines as well as reductive-acetylation of nitroarenes to acetanilides using NaBH4 and Ac2O in water as a green and economic solvent. The copper magnetic clay catalyst can be easily separated from the reaction mixture by an external magnetic field and reused for six consecutive cycles without the significant loss of its catalytic activity. (C) 2019 Elsevier Ltd. All rights reserved.