N-均三甲苯基-3-氧代丁酰胺 | 19359-16-1

• 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-均三甲苯基-3-氧代丁酰胺
• 英文名称: 3-oxo-N-(2,4,6-trimethylphenyl)butanamide
• 英文别名: 2',4',6'-Trimethyl-acetessigsaeureanilid；N-Mesityl-3-oxobutanamide
• CAS: 19359-16-1
• 化学式: C₁₃H₁₇NO₂
• mdl: MFCD00453329
• 分子量: 219.283
• InChiKey: GVBDGMRNGLFNRS-UHFFFAOYSA-N

物化性质

• 沸点：
  358.4±30.0 °C(Predicted)
• 密度：
  1.088±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：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-均三甲苯基-3-氧代丁酰胺 在 N-溴代丁二酰亚胺(NBS) 、 C₂₀H₂₇N₃O₂S 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以96%的产率得到2,2-dibromo-N-(2,4,6-trimethylphenyl)acetamide
  参考文献：
  名称：

  Zwitterion-Catalyzed Deacylative Dihalogenation of β-Oxo Amides

  摘要：

  alpha,alpha-Dihalo-N-arylacetamides are commonly used as intermediates in various organic reactions. In the study described here, a catalytic synthesis of alpha,alpha-dihalo-N-arylacetamides from beta-oxo amides was developed using zwitterionic catalysts and N-halosuccinimides as the halogen sources. The corresponding alpha,alpha-dihalo-N-arylacetamides were obtained in good to excellent yields, and no aromatic halogenated side products were detected. The reaction conditions were mild, and no strong base or acid was required.

  DOI：

  10.1021/acs.orglett.0c02701

文献信息

• Copper-Catalysed (Diacetoxyiodo)benzene-Promoted Aerobic Esterification Reaction: Synthesis of Oxamates from Acetoacetamides
  作者：Zhiguo Zhang、Xiaolong Gao、Haifeng Yu、Guisheng Zhang、Jianming Liu

  DOI：10.1002/adsc.201800616

  日期：2018.9.3

  A copper‐catalysed (diacetoxyiodo)benzene‐promoted aerobic esterification reaction of acetoacetamides was developed for the synthesis of oxamates, which are useful precursors in synthetic organic chemistry. This practical and mild synthetic approach proceeded at 25 °C under open‐air conditions and afforded methyl 2‐oxo‐2‐(phenylamino)acetates in good to excellent yields combined with C−C σ‐bond cleavage

  开发了铜催化（二乙酰氧基碘）苯促进的乙酰乙酰胺需氧酯化反应，以合成草酸盐，草酸盐在合成有机化学中是有用的前体。这种实用且温和的合成方法在露天条件下于25°C进行，提供了具有良好或优异收率的2-氧代-2-（苯基氨基）乙酸甲酯，并带有C-Cσ-键裂解和正式的C-H氧化键功能化。提出了一种机制。
• Preparation and antiinflammatory activity of 2- and 4-pyridones
  作者：James Benjamin Pierce、Zaven S. Ariyan、Gaye Stuart Ovenden

  DOI：10.1021/jm00344a008

  日期：1982.2

  been self-condensed to form pyridones. N-Alkylacetoacetamides give 2-pyridones, while N-arylacetoacetamides give 4-pyridones. In an attempt to develop nonacidic, nonsteroidal antiinflammatory agents, the pyridones were tested in a carrageenan-induced pedal edema assay in rats. While the 2-pyridones were not active, 9 of 17 4-pyridones tested were active, and one compound (4g) had antiinflammatory efficacy

  几种N-烷基和N-芳基乙酰乙酰胺已经自缩合形成吡啶酮。N-烷基乙酰乙酰胺产生2-吡啶酮，而N-芳基乙酰乙酰胺产生4-吡啶酮。为了开发非酸性，非甾体类抗炎药，在卡拉胶中通过大鼠角叉菜胶诱发的踏板水肿试验对吡啶酮进行了测试。虽然2-吡啶酮没有活性，但是测试的17种4-吡啶酮中有9种是活性的，一种化合物（4g）在剂量反应分析（ED50值）中具有抗炎功效。通过标准的多维观察分析法测定小鼠的LD50值，可将大多数化合物视为无毒的。
• Discovery of tetrasubstituted thiophenes as Cisd2 activators: A potential novel therapeutic option in nonalcoholic fatty liver disease
  作者：Chun-Hsu Yao、Zhao-Qing Shen、Yesudoss Christu Rajan、Yu-Wen Huang、Chin-Yu Lin、Jen-Shin Song、Hui-Yi Shiao、Yi-Yu Ke、Yu-Shiou Fan、Chi-Hui Tsai、Teng-Kuang Yeh、Ting-Fen Tsai、Jinq-Chyi Lee

  DOI：10.1016/j.ejmech.2023.115583

  日期：2023.10

  evaluation of a series of Cisd2 activators, all thiophene analogs, based on a hit obtained using two-stage screening and prepared via either the Gewald reaction or by intramolecular aldol-type condensation of an N,S-acetal. Metabolic stability studies of the resulting potent Cisd2 activators suggest that thiophenes 4q and 6 are suitable for in vivo studies. The results from studies on 4q-treated and

  肝脏中 Cisd2 的下调与非酒精性脂肪性肝病 (NAFLD) 的发展有关，因此增加 Cisd2 的水平是此类疾病的潜在治疗方法。在此，我们描述了一系列 Cisd2 激活剂（所有噻吩类似物）的设计、合成和生物学评价，基于使用两阶段筛选获得的命中，并通过 Gewald 反应或 N 的分子内羟醛型缩合制备。，S-缩醛。对所得有效 Cisd2 激活剂的代谢稳定性研究表明，噻吩4q和6适用于体内研究。对4q处理和6处理的 Cisd2hKO-het 小鼠（携带杂合肝细胞特异性 Cisd2 敲除）的研究结果证实（1）Cisd2 水平与 NAFLD 之间存在相关性，（2）这些化合物具有在没有可检测到的毒性的情况下预防 NAFLD 的发生和进展。
• Cope Rearrangement of 1-Acyl-2-vinylcyclopropanes to Cyclohept-4-Enones
  作者：Yinhe Wei、Gang Wang、Zhiguo Zhang、Mengjuan Li、Nana Ma、Hao Wu、Guisheng Zhang

  DOI：10.1021/acs.joc.3c02319

  日期：2024.1.19

  Cycloheptenones are widespread in natural products and bioactive molecules. An efficient and convenient NaH-mediated Cope Rearrangement of doubly activated vinylcyclopropanes is reported for the synthesis of cyclohepten-4-ones. These flexible intramolecular reactions were applicable to a wide range of substrates and could be performed on gram scale. The derivatization of the product leads to short

  环庚烯酮广泛存在于天然产物和生物活性分子中。据报道，一种高效且方便的 NaH 介导的双活化乙烯基环丙烷 Cope 重排用于环庚烯-4-酮的合成。这些灵活的分子内反应适用于多种底物，并且可以在克规模上进行。产品的衍生化可以快速高效地合成一些有用的功能分子。
• PIERCE, J. B.;ARIYAN, Z. S.;OVENDEN, G. S., J. MED. CHEM., 1982, 25, N 2, 131-136
  作者：PIERCE, J. B.、ARIYAN, Z. S.、OVENDEN, G. S.

  DOI：——

  日期：——