4-bromo-N-(pyridin-2-ylmethyl)benzamide | 313985-45-4

• 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-bromo-N-(pyridin-2-ylmethyl)benzamide
• CAS: 313985-45-4
• 化学式: C₁₃H₁₁BrN₂O
• mdl: MFCD00434487
• 分子量: 291.147
• InChiKey: QFFQUGRPENSEGB-UHFFFAOYSA-N

物化性质

• 熔点：
  117-118 °C
• 沸点：
  459.6±35.0 °C(Predicted)
• 密度：
  1.456±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-bromo-N-(pyridin-2-ylmethyl)benzamide 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 sodium acetate 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 0.3h， 生成 4′-tert-butyl-N-(pyridin-2-ylmethyl)[1,1′-biphenyl]-4-carboxamide
  参考文献：
  名称：

  One-Pot Approach to N-Quinolyl 3′/4′-Biaryl Carboxamides by Microwave-Assisted Suzuki–Miyaura Coupling and N-Boc Deprotection

  摘要：

  N-Quinolyl biaryl carboxamides have received tremendous attention for their notable biological properties. Here we have described a general protocol for the preparation of N-quinolyl 3'/4'-biaryl carboxamides by microwave-assisted Suzuki-Miyaura cross-coupling reaction and N-Boc deprotection in one pot. This method, which did not require acids, was used to produce a series of N-quinolyl 3'/4'-biaryl carboxamides with excellent functional group tolerance and high yields (70% to 95%).

  DOI：

  10.1021/acs.joc.6b01725
• 作为产物：
  描述：

  2-氨甲基吡啶 、 4-溴苯甲酸 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以94%的产率得到4-bromo-N-(pyridin-2-ylmethyl)benzamide
  参考文献：
  名称：

  One-Pot Approach to N-Quinolyl 3′/4′-Biaryl Carboxamides by Microwave-Assisted Suzuki–Miyaura Coupling and N-Boc Deprotection

  摘要：

  N-Quinolyl biaryl carboxamides have received tremendous attention for their notable biological properties. Here we have described a general protocol for the preparation of N-quinolyl 3'/4'-biaryl carboxamides by microwave-assisted Suzuki-Miyaura cross-coupling reaction and N-Boc deprotection in one pot. This method, which did not require acids, was used to produce a series of N-quinolyl 3'/4'-biaryl carboxamides with excellent functional group tolerance and high yields (70% to 95%).

  DOI：

  10.1021/acs.joc.6b01725

文献信息

• <i>N</i>-acylation of amides through internal nucleophilic catalysis
  作者：Meng Yao、Xia Chen、Yuling Lu、Zhenhua Guan、Zengwei Luo、Yonghui Zhang

  DOI：10.1177/1747519820925755

  日期：2021.1

  An efficient method for N-acylation of amides is described using a pyridine ring as the internal nucleophilic catalyst to give imides in moderate to excellent yields. The methodology provides a facile, air insensitive, and environmentally friendly route to form diversified imide scaffolds, which exist widely in natural products and biologically active materials.

  描述了一种使用吡啶环作为内部亲核催化剂的酰胺N-酰化的有效方法，以中等至极好的收率得到酰亚胺。该方法提供了一种容易，对空气不敏感且对环境友好的途径来形成多样化的酰亚胺支架，该支架广泛存在于天然产物和生物活性材料中。
• Cobalt-Catalyzed Carbonylative Synthesis of Phthalimides from <i>N</i>-(Pyridin-2-ylmethyl)benzamides with TFBen as the CO Source
  作者：Lu-Yang Fu、Jun Ying、Xiao-Feng Wu

  DOI：10.1021/acs.joc.9b01890

  日期：2019.10.4

  A cobalt-catalyzed direct carbonylative synthesis of phthalimide motifs from N-(pyridin-2-ylmethyl)benzamides has been developed. Various phthalimide derivatives were obtained in moderate to excellent yields (up to 98%) by using 2-picolylamine as an efficient directing group and benzene-1,3,5-triyl triformate (TFBen) as a convenient CO surrogate.

  已经开发了由N-（吡啶-2-基甲基）苯甲酰胺钴催化的邻苯二甲酰亚胺基序的直接羰基合成。通过使用2-吡啶甲基胺作为有效的导向基团和苯-1,3,5-三甲酸三甲酸酯（TFBen）作为常规的CO替代物，可以中等至极好的收率（高达98％）获得各种邻苯二甲酰亚胺衍生物。
• Rh(<scp>i</scp>)-Catalyzed [3+2] annulation reactions of cyclopropenones with amides
  作者：Akira Haito、Naoto Chatani

  DOI：10.1039/c9cc02397f

  日期：——

  Rh(I)-Catalyzed [3+2] annulation reactions of cyclopropenones with amides are reported. The reaction provides a direct approach for producing highly substituted α,β-unsaturated γ-lactam derivatives. The presence of an N(sp2) atom in the N-alkyl group of the amide, such as the 2-pyridinylmethyl or 8-aminoquinonyl group, is essential for the success of the reaction.

  报道了Rh（I）催化的环丙烯酮与酰胺的[3 + 2]环化反应。该反应提供了直接的方法来制备高度取代的α，β-不饱和γ-内酰胺衍生物。在酰胺的N-烷基中存在N（sp 2）原子，例如2-吡啶基甲基或8-氨基喹啉基，对于成功的反应是必不可少的。
• Inoue, Satoshi; Shiota, Hirotaka; Fukumoto, Yoshiya, Journal of the American Chemical Society, 2009, vol. 131, p. 6898 - 6899
  作者：Inoue, Satoshi、Shiota, Hirotaka、Fukumoto, Yoshiya、Chatani, Naoto

  DOI：——

  日期：——
• One-Pot Approach to <i>N</i>-Quinolyl 3′/4′-Biaryl Carboxamides by Microwave-Assisted Suzuki–Miyaura Coupling and <i>N</i>-Boc Deprotection
  作者：Zhi-You Huang、Jing-Fang Yang、Ke Song、Qian Chen、Shao-Lin Zhou、Ge-Fei Hao、Guang-Fu Yang

  DOI：10.1021/acs.joc.6b01725

  日期：2016.10.21

  N-Quinolyl biaryl carboxamides have received tremendous attention for their notable biological properties. Here we have described a general protocol for the preparation of N-quinolyl 3'/4'-biaryl carboxamides by microwave-assisted Suzuki-Miyaura cross-coupling reaction and N-Boc deprotection in one pot. This method, which did not require acids, was used to produce a series of N-quinolyl 3'/4'-biaryl carboxamides with excellent functional group tolerance and high yields (70% to 95%).