2,4-dichloro-N-(pyridin-2-yl)benzamide | 326883-43-6

• 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: 2,4-dichloro-N-(pyridin-2-yl)benzamide
• 英文别名: 2,4-dichloro-N-(2-pyridinyl)benzamide；2,4-dichloro-N-pyridin-2-ylbenzamide
• CAS: 326883-43-6
• 化学式: C₁₂H₈Cl₂N₂O
• 分子量: 267.114
• InChiKey: LSLXBZDDOIFEFO-UHFFFAOYSA-N

物化性质

• 沸点：
  346.6±37.0 °C(Predicted)
• 密度：
  1.440±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氨基吡啶 、 2,4-二氯苯甲醛 在 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以66%的产率得到2,4-dichloro-N-(pyridin-2-yl)benzamide
  参考文献：
  名称：

  Copper-catalyzed dehydrogenative reaction: synthesis of amide from aldehydes and aminopyridine

  摘要：

  We have developed a highly efficient method in the presence of copper catalyst to form amides from aminopyridines and aldehydes. This method is simple, environmental benign and has practical advantages in the amide synthesis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.072

文献信息

• Metal-Free Synthesis of <i>N</i>-(Pyridine-2-yl)amides from Ketones via Selective Oxidative Cleavage of C(O)–C(Alkyl) Bond in Water
  作者：Yanpeng Liu、Honghao Sun、Zhangjian Huang、Cong Ma、Aijun Lin、Hequan Yao、Jinyi Xu、Shengtao Xu

  DOI：10.1021/acs.joc.8b01956

  日期：2018.12.7

  N-(pyridine-2-yl)amides in water from ketones and 2-aminopyridine via direct oxidative C–C bond cleavage has been developed. A series of ketones, including more challenging inactive aromatic ketones substituted with diverse long-chain alkyl groups, were selectively converted to N-(pyridine-2-yl)amides. Furthermore, the protocol can be applied to aryl alkyl carbinols to afford the corresponding amides in moderate

  已经开发了TBHP / TBAI介导的通过直接氧化CC键从酮和2-氨基吡啶合成水中N-（吡啶-2-基）酰胺的方法。一系列酮，包括被各种长链烷基取代的更具挑战性的惰性芳族酮，被选择性地转化为N-（吡啶-2-基）酰胺。此外，该方案可以应用于芳基烷基甲醇，以中等至良好的产率得到相应的酰胺。
• Singlet oxygen mediated one pot synthesis of N-pyridinylamides via oxidative amidation of aryl alkyl ketones
  作者：Firdoos Ahmad Sofi、Rohit Sharma、S.N. Kavyasree、Sumi Aisha Salim、Pravin J. Wanjari、Prasad V. Bharatam

  DOI：10.1016/j.tet.2019.130536

  日期：2019.10

  An environmental friendly, efficient protocol has been realized for the synthesis of N-pyridinylamides via copper catalyzed oxidative amidation of aryl alkyl ketones with 2-aminopyridines. This one pot protocol involves chemo selective cleavage of C (O)–C bond in the presence of singlet oxygen. The reaction conditions are simple, tolerates wide range of substrates and the products were formed in good

  通过芳基烷基酮与2-氨基吡啶的铜催化氧化酰胺化合成N-吡啶基酰胺已经实现了环境友好的有效方案。这个一锅法涉及在单线态氧存在下化学选择性裂解C（O）–C键。反应条件简单，可耐受多种底物，并且以良好至极好的产率形成产物。该方法相对于较早的成功生成N-吡啶基酰胺的尝试提供了适度的改进。
• Chemodivergent synthesis of <i>N</i>-(pyridin-2-yl)amides and 3-bromoimidazo[1,2-<i>a</i>]pyridines from α-bromoketones and 2-aminopyridines
  作者：Yanpeng Liu、Lixue Lu、Haipin Zhou、Feijie Xu、Cong Ma、Zhangjian Huang、Jinyi Xu、Shengtao Xu

  DOI：10.1039/c9ra06724h

  日期：——

  N-(Pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines were synthesized respectively from α-bromoketones and 2-aminopyridine under different reaction conditions. N-(Pyridin-2-yl)amides were formed in toluene via C–C bond cleavage promoted by I2 and TBHP and the reaction conditions were mild and metal-free. Whereas 3-bromoimidazopyridines were obtained in ethyl acetate via one-pot tandem cyclization/bromination

  以α-溴酮和2-氨基吡啶在不同反应条件下分别合成N- (吡啶-2-基)酰胺和3-溴咪唑并[1,2- a ]吡啶。N- (Pyridin-2-yl)amides 在甲苯中通过I 2和 TBHP促进的 C-C 键断裂形成，反应条件温和且不含金属。3-溴咪唑并吡啶在乙酸乙酯中通过一锅串联环化/溴化仅加入TBHP得到，而进一步溴化促进环化形成咪唑并吡啶，不需要碱，多功能的3-溴咪唑并吡啶可以进一步转移到其他骷髅。
• Copper-catalyzed dehydrogenative reaction: synthesis of amide from aldehydes and aminopyridine
  作者：Sizhuo Yang、Hao Yan、Xiaoyu Ren、Xiaokang Shi、Jian Li、Yuling Wang、Guosheng Huang

  DOI：10.1016/j.tet.2013.05.072

  日期：2013.8

  We have developed a highly efficient method in the presence of copper catalyst to form amides from aminopyridines and aldehydes. This method is simple, environmental benign and has practical advantages in the amide synthesis. (C) 2013 Elsevier Ltd. All rights reserved.