4-氯-N-(4-氯苄基)苯甲酰胺 | 130780-10-8

• 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: 4-氯-N-(4-氯苄基)苯甲酰胺
• 英文名称: 4-chloro-N-(4-chlorobenzyl)benzamide
• 英文别名: N-(4-chlorobenzyl)-4-chlorobenzamide；4-chloro-N-[(4-chlorophenyl)methyl]benzamide
• CAS: 130780-10-8
• 化学式: C₁₄H₁₁Cl₂NO
• 分子量: 280.153
• InChiKey: ZXNZBJZGAQTCRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-氯-N-(4-氯苄基)苯甲酰胺 在 氯化亚砜 作用下， 生成 4-chloro-N-(4-chlorobenzyl)benzimidoyl chloride
  参考文献：
  名称：

  Synthesis of Bis(2,4-diarylimidazol-5-yl) Diselenides from N-Benzylbenzimidoyl Isoselenocyanates

  摘要：

  The reaction of N-benzylbenzamides 6 with SOCl2 under reflux gave the corresponding N-benzylbenzimidoyl chlorides 7. Further treatment with KSeCN in dry acetone yielded imidoyl isosclenocyanates 3 (Scheme 2). These compounds, obtained in satisfying yields, proved to be stable enough to be purified and analyzed. Reaction of 3 with morpholine in dry acetone led to the corresponding selonourea derivatives 8. On treatment with Et3N, the 4-nitrobenzyl derivatives of type 3 were transformed into bis(2,4-diarylimidazol-5-yl) diselenides 9 (Scheme 3). This transformation takes place only when the benzyl residue bears an NO2 group and the phenyl group is not substituted with a strong electron-donating group. A reaction mechanism for the formation of 9 is proposed in Scheme 4. The key structures have been established by X-ray crystallography.

  DOI：

  10.1002/1522-2675(200204)85:4<1102::aid-hlca1102>3.0.co;2-t
• 作为产物：
  描述：

  C₇H₇Cl₂N 在 叔丁基过氧化氢 作用下， 以 水 、 乙腈 为溶剂， 反应 48.0h， 以78%的产率得到4-氯-N-(4-氯苄基)苯甲酰胺
  参考文献：
  名称：

  Visible light-promoted self-coupling of N-chloramines at room temperature: A metal-free access to substituted amides

  摘要：

  An efficient protocol to synthesize substituted amides via self-coupling of N-chlorobenzylamines has been developed under visible light-promoted mild condition. Both the electron-deficient and electron-rich benzylamines undergo self-coupling very readily to produce the amide linkage under given reaction conditions.

  DOI：

  10.1080/00397911.2019.1678172

文献信息

• Nafion®-catalyzed microwave-assisted Ritter reaction: an atom-economic solvent-free synthesis of amides
  作者：Vivek Polshettiwar、Rajender S. Varma

  DOI：10.1016/j.tetlet.2008.02.009

  日期：2008.4

  An atom-economic solvent-free synthesis of amides by the Ritter reaction of alcohols and nitriles under microwave irradiation is reported. This green protocol is catalyzed by solid-supported Nafion®NR50 with improved efficiency and reduced waste production.

  报道了在微波辐射下通过醇和腈的Ritter反应的无原子经济的无溶剂合成酰胺。此绿色协议由固体负载的Nafion催化® NR50具有提高的效率和降低的生产废物。
• Method and amines used therein
  申请人：John Wyeth & Brother, Limited

  公开号：US05321047A1

  公开（公告）日：1994-06-14

  The invention concerns a method for treating depression or senile dementia using a compound which acts selectively as an agohist of gamma aminobutyric acid (GABA) at GABA autoreceptors with the proviso that the compound is not fengabine and progabide.

  该发明涉及一种治疗抑郁症或老年性痴呆的方法，使用一种化合物，该化合物在GABA自受体上选择性地作为γ-氨基丁酸（GABA）的激动剂起作用，但前提是该化合物不是风加宾和丙加必。
• Design and Synthesis of Arylamidine Derivatives as Serotonin/Norepinephrine Dual Reuptake Inhibitors
  作者：Hui Wen、Wen Qin、Guangzhong Yang、Yanshen Guo

  DOI：10.3390/molecules24030497

  日期：——

  To improve the in vivo antidepressant activity of previously reported serotonin (5-HT) and norepinephrine (NE) dual reuptake inhibitors, three series of arylamidine derivatives were designed and synthesized. The in vitro 5-HT and NE reuptake inhibitory activities of these compounds were evaluated, and compound II-5 was identified as the most potent 5-HT (IC50 = 620 nM) and NE (IC50 = 10 nM) dual reuptake

  为了提高先前报道的5-羟色胺（5-HT）和去甲肾上腺素（NE）双重再摄取抑制剂的体内抗抑郁活性，设计并合成了三个系列的芳基idine胺衍生物。评估了这些化合物的体外5-HT和NE重摄取抑制活性，化合物II-5被确定为最有效的5-HT（IC50 = 620 nM）和NE（IC50 = 10 nM）双重重摄取抑制剂。化合物II-5在大鼠尾部悬吊试验中显示出有效的抗抑郁活性，并在小鼠的初步急性毒性试验中显示出可接受的安全性。我们的结果表明，这些芳酰胺衍生物表现出有效的5-HT / NE双重再摄取抑制作用，应作为抗抑郁药候选者进行进一步研究。
• Deoxygenative Nucleophilic Phosphonation and Electrophilic Alkylation of Secondary Amides: A Facile Access to Quaternary α-Aminophosphonates
  作者：Jiaxiang Lu、Zhenghua Li、Li Deng

  DOI：10.1021/jacs.3c14517

  日期：2024.2.21

  synthetic accessibility of amides render them valuable precursors for the synthesis of diverse nitrogen-containing compounds. Herein, we present a metal-free and streamlined synthetic strategy for the synthesis of quaternary α-aminophosphonates. This approach involves sequential deoxygenative nucleophilic phosphonation and versatile electrophilic alkylation of secondary amides in a one-pot fashion. Notably

  酰胺的广泛存在和合成可及性使其成为合成各种含氮化合物的宝贵前体。在此，我们提出了一种用于合成 α-氨基膦酸季盐的无金属且简化的合成策略。该方法涉及一锅法中仲酰胺的连续脱氧亲核磷酸化和多功能亲电烷基化。值得注意的是，该方法首次实现了仲酰胺与亲核试剂和亲电试剂的直接双官能化，通过简单的衍生化，通过水解产生有价值的游离α-氨基膦酸酯。该协议具有操作简单、功能组广泛兼容性、环境友好以及可扩展到多克数量的优点。
• Agonist of gamma-aminobutyric acid
  申请人：JOHN WYETH & BROTHER LIMITED

  公开号：EP0345068A2

  公开（公告）日：1989-12-06

  The invention concerns a method for treating depression or senile dementia using a compound which acts selectively as an agonist of gamma aminobutyric acid (GABA) at GABA autoreceptors with the proviso that the compound is not fengabine and progabide.

  本发明涉及一种使用化合物治疗抑郁症或老年痴呆症的方法，该化合物在 GABA 自体受体上选择性地充当γ-氨基丁酸（GABA）的激动剂，但该化合物不是芬那宾和普罗加比。