4-cyano-N-(4-chlorobenzyl)benzamide | 464934-87-0

• 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: 4-cyano-N-(4-chlorobenzyl)benzamide
• 英文别名: N-(4-chlorobenzyl)-4-cyanobenzamide；N-[(4-chlorophenyl)methyl]-4-cyanobenzamide
• CAS: 464934-87-0
• 化学式: C₁₅H₁₁ClN₂O
• 分子量: 270.718
• InChiKey: KOUNPDGIKKWSCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-cyano-N-(4-chlorobenzyl)benzamide 在 氯化亚砜 作用下， 生成 N-(4-chlorobenzyl)-4-cyanobenzimidoyl 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：

  对氰基苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-cyano-N-(4-chlorobenzyl)benzamide
  参考文献：
  名称：

  仲酰胺的脱氧亲核磷酸化和亲电烷基化：轻松获得季α-氨基膦酸盐

  摘要：

  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。

  DOI：

  10.1021/jacs.3c14517

文献信息

• 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。
• Synthesis of Bis(2,4-diarylimidazol-5-yl) Diselenides from N-Benzylbenzimidoyl Isoselenocyanates
  作者：Plamen K. Atanassov、Yuehui Zhou、Anthony Linden、Heinz Heimgartner

  DOI：10.1002/1522-2675(200204)85:4<1102::aid-hlca1102>3.0.co;2-t

  日期：2002.4

  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.
• 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。