N-(2,6-二氯苯基)-4-甲氧基苯甲酰胺 | 157491-16-2

• 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-(2,6-二氯苯基)-4-甲氧基苯甲酰胺
• 英文名称: N-(2,6-dichlorophenyl)-4-methoxybenzamide
• 英文别名: 2',6'-dichloro-4-methoxybenzanilide
• CAS: 157491-16-2
• 化学式: C₁₄H₁₁Cl₂NO₂
• 分子量: 296.153
• InChiKey: DLSZPRUJGBYYHP-UHFFFAOYSA-N

物化性质

• 沸点：
  346.6±42.0 °C(Predicted)
• 密度：
  1.369±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-甲氧基二苯甲醇 在 盐酸 、 tetrafluoroboric acid 、 calcium chloride 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 生成 N-(2,6-二氯苯基)-4-甲氧基苯甲酰胺
  参考文献：
  名称：

  Reactions between Nitrile Oxides and Carbenium Ions: Synthesis of Benzoxazines, Oximes, and Amides through Intramolecular ortho or ipso Attack

  摘要：

  Reactions between nitrite oxides and benzylic carbocations are described. Different results were obtained when the carbocations were generated from the corresponding chlorides with different Lewis acids, with addition products such as benzoxazines, oximes, and amides being produced. Primary, secondary, and tertiary carbocations showed different reactivities. The product ratios strongly depended on the substituents on the aromatic ring of the benzylic carbocations. Evidence for the proposed mechanism is reported. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

  DOI：

  10.1002/1099-0690(200207)2002:14<2411::aid-ejoc2411>3.0.co;2-n

文献信息

• Selective radical amination of aldehydic C(sp²)–H bonds with fluoroaryl azides via Co(<scp>ii</scp>)-based metalloradical catalysis: synthesis of N-fluoroaryl amides from aldehydes under neutral and nonoxidative conditions
  作者：Li-Mei Jin、Hongjian Lu、Yuan Cui、Christopher L. Lizardi、Thiago N. Arzua、Lukasz Wojtas、Xin Cui、X. Peter Zhang

  DOI：10.1039/c4sc00697f

  日期：——

  proven to be an effective metalloradical catalyst for intermolecular amination of C(sp2)–H bonds of aldehydes with fluoroaryl azides. The [Co(P1)]-catalyzed process can employ aldehydes as the limiting reagents and operate under neutral and nonoxidative conditions, generating nitrogen gas as the only byproduct. The metalloradical aldehydic C–H amination is suitable for different combinations of aldehydes

  D 2h对称酰胺卟啉 3,5-Di t Bu-IbuPhyrin [Co( P1 )]的 Co( II ) 配合物已被证明是一种有效的金属基催化剂，用于 C(sp 2 )–H 键的分子间胺化醛与氟芳基叠氮化物。[Co( P1 )]-催化过程可以使用醛作为限制试剂并在中性和非氧化条件下运行，产生氮气作为唯一的副产品。金属基醛 C-H 胺化适用于醛和氟芳基叠氮化物的不同组合，产生相应的N-氟芳基酰胺的产率非常好。一系列机理研究支持 Co( II ) 催化的分子间 C-H 胺化的逐步自由基机制。
• Microwave-Assisted Organic Synthesis, structure–activity relationship, kinetics and molecular docking studies of non-cytotoxic benzamide derivatives as selective butyrylcholinesterase inhibitors
  作者：Sheeba Wajid、Asma Khatoon、Maria Aqeel Khan、Humaira Zafar、Shama Kanwal、Atta-ur-Rahman、M. Iqbal Choudhary、Fatima Z. Basha

  DOI：10.1016/j.bmc.2019.07.015

  日期：2019.9

  A series of benzamide derivatives 1–12 with various functional groups (–H, –Br, –F, –OCH3, –OC2H5, and –NO2) was synthesized using an economic, and facile Microwave-Assisted Organic Synthesis, and evaluated for acetylcholinesterase (ACHE) and butyrylcholinesterase (BCHE) activity in vitro. Structure–activity relationship showed that the substitution of –Br group influenced the inhibitory activity against

  一系列的苯甲酰胺衍生物的1 - 12与各种官能团（-H，-Br，-F，-OCH 3，-OC 2 H ^ 5，和-NO 2）用一种经济合成，并且容易微波辅助有机合成，并评估其在体外的乙酰胆碱酯酶（ACHE）和丁酰胆碱酯酶（BCHE）活性。结构-活性关系表明，-Br基团的取代影响了对BCHE酶的抑制活性。发现合成的化合物是BCHE的选择性抑制剂。另外，所有的化合物1 - 12被认为是无细胞毒性的，相比于标准放线菌酮（IC50  = 0.8±0.2 µM）。其中， 与标准加兰他敏氢溴酸盐（IC 50  = 40.83±0.37 µM）相比，化合物3表现出最有效的BCHE抑制活性（IC 50 = 0.8±0.6 µM）。酶动力学研究表明，化合物1，3 - 4，和7 - 8表现为抑制对BCHE的混合模式中，当化合物2，5 - 6和9表现出非竞争性的抑制模式。分子对接研究进一步强调了这些抑制剂与具有催
• Nitrile Oxide-BF3 complex as electrophilic moiety towards aromatic systems: Stereospecific synthesis of oximes
  作者：Sergio Auricchio、Antonella Bini、Eros Pastormerlo、Aldo Ricca、Ada M. Truscello

  DOI：10.1016/s0040-4020(01)90486-7

  日期：——

  Aromatic Oximes are obtained stereospecifically by action of Nitrile Oxide-BF3 complexes on Aromatic Compounds.
• Auricchio Sergio, Bini Antonella, Pastormerlo Eros, Ricca Aldo, Truscello+, Tetrahedron, 50 (1994) N 25, S 7589-7596
  作者：Auricchio Sergio, Bini Antonella, Pastormerlo Eros, Ricca Aldo, Truscello+

  DOI：——

  日期：——
• Reactions between Nitrile Oxides and Carbenium Ions: Synthesis of Benzoxazines, Oximes, and Amides through Intramolecular ortho or ipso Attack
  作者：Sergio Auricchio、Caterina Magnani、Ada M. Truscello

  DOI：10.1002/1099-0690(200207)2002:14<2411::aid-ejoc2411>3.0.co;2-n

  日期：2002.7

  Reactions between nitrite oxides and benzylic carbocations are described. Different results were obtained when the carbocations were generated from the corresponding chlorides with different Lewis acids, with addition products such as benzoxazines, oximes, and amides being produced. Primary, secondary, and tertiary carbocations showed different reactivities. The product ratios strongly depended on the substituents on the aromatic ring of the benzylic carbocations. Evidence for the proposed mechanism is reported. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).