N-<(benzotriazol-1-yl)(4-chlorophenyl)methyl>benzamide | 138768-30-6

• 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-<(benzotriazol-1-yl)(4-chlorophenyl)methyl>benzamide
• 英文别名: N-((1H-benzo[d][1,2,3]triazol-1-yl)(4-chlorophenyl)methyl)benzamide；N-[benzotriazol-1-yl(4-chlorophenyl)]methylbenzamide；N-[benzotriazol-1-yl-(4-chlorophenyl)methyl]benzamide
• CAS: 138768-30-6
• 化学式: C₂₀H₁₅ClN₄O
• 分子量: 362.818
• InChiKey: NCZWTZGWNMWJQH-UHFFFAOYSA-N

物化性质

• 沸点：
  648.7±55.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  59.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-<(benzotriazol-1-yl)(4-chlorophenyl)methyl>benzamide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以1 g的产率得到N-benzoyl-1-methoxy-1-(p-chlorophenyl)-methylamine
  参考文献：
  名称：

  Heterobimetallic Ir–Sn catalysis: aza-Friedel–Crafts reaction of N-sulfonyl aldimines

  摘要：

  The heterobimetallic complex [Ir(COD)(SnCl3)Cl(mu-Cl)](2) catalyzes the aza-Friedel Crafts reaction of 1,3,5-trimethoxybenzene, as well as substituted indoles with N-sulfonyl aldimines leading to the formation of diarylamines and triarylmethanes in good yields. The symmetrical triarylmethanes were also obtained from diarylamines and suitable nucleophiles via simultaneous cleavage of sp(3) C-N bond and elimination of 1,3,5-trimethoxybenzene. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.074
• 作为产物：
  描述：

  邻苯二胺 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 、 甲苯 为溶剂， 反应 24.0h， 生成 N-<(benzotriazol-1-yl)(4-chlorophenyl)methyl>benzamide
  参考文献：
  名称：

  Heterobimetallic Ir–Sn catalysis: aza-Friedel–Crafts reaction of N-sulfonyl aldimines

  摘要：

  The heterobimetallic complex [Ir(COD)(SnCl3)Cl(mu-Cl)](2) catalyzes the aza-Friedel Crafts reaction of 1,3,5-trimethoxybenzene, as well as substituted indoles with N-sulfonyl aldimines leading to the formation of diarylamines and triarylmethanes in good yields. The symmetrical triarylmethanes were also obtained from diarylamines and suitable nucleophiles via simultaneous cleavage of sp(3) C-N bond and elimination of 1,3,5-trimethoxybenzene. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.074

文献信息

• A General and Convenient Synthesis of <i>N</i>-[(1. Diphenyl-oxophosphinyl)alkyl]carboxamides and Sulfamide
  作者：Alan R. Katritzky、Hong Wu、Linghong Xie

  DOI：10.1080/00397919508012682

  日期：1995.4

  Abstract A wide range of title compounds were prepared in good yields by amidoalkylation of ethyl diphenylphosphinite with readily available N-α-(benzotriazol-1-yl)alkyl]amides. A more convenient direct one-pot amidoalkylation of ethyl diphenylphosphinite with an amide, an aldehyde and benzotriazole is described.

  摘要 通过使用易得的 N-α-(苯并三唑-1-基)烷基]酰胺对二苯基亚膦酸乙酯进行酰胺烷基化反应，以良好的收率制备了多种标题化合物。描述了用酰胺、醛和苯并三唑对二苯基亚膦酸乙酯进行更方便的直接一锅酰胺烷基化。
• Dy(OTf)3-mediated selective substitution of N-(α-benzotriazolyl-alkyl)amides with active methylene compounds for synthesis of benzotriazole derivatives
  作者：Weixun Li、Yang Ye、Jin Zhang、Renhua Fan

  DOI：10.1016/j.tetlet.2009.07.098

  日期：2009.9

  A Dy(OTf)3-mediated selective substitution reaction of N-(α-benzotriazolyl-alkyl)amides with active methylene compounds is reported. The present procedure provides a facile method for the synthesis of benzotriazole derivatives.

  报道了Dy（OTf）3介导的N-（α-苯并三唑基-烷基）酰胺与活性亚甲基化合物的选择性取代反应。本方法提供了合成苯并三唑衍生物的简便方法。
• Cross-coupling of Aromatic Aldehydes with N-(Amidobenzyl)benzotriazoles: An Alternative Route to α-Amidoketones
  作者：Wijitra Waengdongbung、Mongkol Nontakitticharoen、Viwat Hahnvajanawong

  DOI：10.2174/1570178615666171221143115

  日期：2018.8.8

  N-dimethylbenzimidazolium iodide which is a safe and recyclable organic pre-catalyst, along with N-(amidobenzyl)benzotriazoles as activated N-acylimines for this cross-coupling reaction. Method: N-(Amidobenzyl)benzotriazoles (9a-c) were prepared from benzamide, aromatic aldehydes and benzotriazole. N,N-Dimethylbenzimidazolium iodide (11) was easily prepared via the methylation reaction of benzimidazole

  背景：几种过渡金属催化的反应已用于合成具有生物活性的α-酰胺酮。这些方法涉及不方便的条件或昂贵的催化剂。还已经报道了基于无过渡金属的催化剂的替代尝试，包括在作为有机催化剂的噻唑鎓盐存在下醛与嘧啶的交叉偶联反应。我们在此报告了N，N-二甲基苯并咪唑碘化物作为一种安全的和可循环使用的有机预催化剂，以及N-（酰氨基苄基）苯并三唑作为活化的N-酰基酰亚胺的交叉偶联反应。 方法：由苯甲酰胺，芳族醛和苯并三唑制备N-（酰胺基苄基）苯并三唑（9a-c）。通过苯并咪唑的甲基化反应可以容易地制备N，N-二甲基苯并咪唑碘化物（11）。在DBU和有机催化剂11的存在下，在回流的THF中进行交叉偶联反应5小时。 结果：N，N-二甲基苯并咪唑鎓催化的各种芳族醛（10a-f）与N-（酰氨基苄基）苯并三唑（9a-c）的交叉偶联反应以良好的收率得到了α-酰胺酮（12a-r）。 结论：基于芳族醛与酰基亚胺的有机催化交叉偶联
• N-[1-(Benzotriazol-1-yl)alkyl]amides, versatile amidoalkylation reagents. Part 4. A New Synthetic Route to 4H-1,3-Oxazines
  作者：Alan R. Katritzky、J. Pernak、Wei-Qiang Fan

  DOI：10.1002/prac.19923340203

  日期：——

  A variety of 2,4,6-tri- and 2,4,5,6-tetrasubstituted 4H-1,3-oxazines (7 a-i) were synthesized in excellent yields by the reaction of acetylenes (5) in the presence of aluminum chloride with N-[1-(benzotriazol-1-yl) alkyl]amides 4, themselves readily prepared from benzotriazole (1) with amides (2) and aldehydes (3).
• Heterobimetallic Ir–Sn catalysis: aza-Friedel–Crafts reaction of N-sulfonyl aldimines
  作者：Paresh Nath Chatterjee、Arnab Kumar Maity、Swapna Sarita Mohapatra、Sujit Roy

  DOI：10.1016/j.tet.2013.01.074

  日期：2013.4

  The heterobimetallic complex [Ir(COD)(SnCl3)Cl(mu-Cl)](2) catalyzes the aza-Friedel Crafts reaction of 1,3,5-trimethoxybenzene, as well as substituted indoles with N-sulfonyl aldimines leading to the formation of diarylamines and triarylmethanes in good yields. The symmetrical triarylmethanes were also obtained from diarylamines and suitable nucleophiles via simultaneous cleavage of sp(3) C-N bond and elimination of 1,3,5-trimethoxybenzene. (C) 2013 Elsevier Ltd. All rights reserved.