2-bromo-N-[tert-butylcarbamoyl-(4-chlorophenyl)methyl]-N-prop-2-ynylbenzamide | 1404471-53-9

• 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-bromo-N-[tert-butylcarbamoyl-(4-chlorophenyl)methyl]-N-prop-2-ynylbenzamide
• 英文别名: 2-bromo-N-[2-(tert-butylamino)-1-(4-chlorophenyl)-2-oxoethyl]-N-(prop-2-yn-1-yl)benzamide；2-bromo-N-[2-(tert-butylamino)-1-(4-chlorophenyl)-2-oxoethyl]-N-prop-2-ynylbenzamide
• CAS: 1404471-53-9
• 化学式: C₂₂H₂₂BrClN₂O₂
• 分子量: 461.786
• InChiKey: UKOYBMCDPSSUCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-N-[tert-butylcarbamoyl-(4-chlorophenyl)methyl]-N-prop-2-ynylbenzamide 在 三乙基硅烷 、 potassium tert-butylate 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 23.5h， 生成 1-(2-bromobenzoyl)-N-tert-butyl-2-(4-chlorophenyl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Two-Step Synthesis of 2,3-Dihydropyrroles via a Formal 5-endo Cycloisomerization of Ugi 4-CR/Propargyl Adducts

  摘要：

  A practical two-step synthesis of 2,3-dihydropyrroles from Ugi 4-CR/propargyl adducts is presented. The protocol includes a base-mediated formation of an allenamide functional group and an in situ metal-free formal 5-endo cycloisomerization that occurs in a highly regioselective manner at the allenamide C-gamma.

  DOI：

  10.1021/ol3024727
• 作为产物：
  描述：

  tert-butyl isocyanide 、 4-氯苯甲醛 、 炔丙胺 、 2-溴苯甲酸 在 indium(III) chloride 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以77%的产率得到2-bromo-N-[tert-butylcarbamoyl-(4-chlorophenyl)methyl]-N-prop-2-ynylbenzamide
  参考文献：
  名称：

  Two-Step Synthesis of 2,3-Dihydropyrroles via a Formal 5-endo Cycloisomerization of Ugi 4-CR/Propargyl Adducts

  摘要：

  A practical two-step synthesis of 2,3-dihydropyrroles from Ugi 4-CR/propargyl adducts is presented. The protocol includes a base-mediated formation of an allenamide functional group and an in situ metal-free formal 5-endo cycloisomerization that occurs in a highly regioselective manner at the allenamide C-gamma.

  DOI：

  10.1021/ol3024727

文献信息

• Palladium-Catalyzed Regioselective Heck–Suzuki–Miyaura Cascade Cyclization for the Synthesis of Trisubstituted Arylideneisoquinolinones
  作者：M. Asgari、R. Mirzazadeh、B. Larijani、P. Rashidi Ranjbar、R. Rahimi、M. Mahdavi

  DOI：10.1055/s-0037-1611804

  日期：2019.6

  An Ugi four-component reaction was used to construct propargylamide starting materials for a subsequent domino Heck–Suzuki–Miyaura cross-coupling reaction to give derivatives of 4-benzylidene-1-oxo-3,4-dihydro-1H-isoquinoline.

  Ugi 四组分反应用于构建炔丙基酰胺起始材料，用于随后的多米诺 Heck-Suzuki-Miyaura 交叉偶联反应，以得到 4-benzylidene-1-oxo-3,4-dihydro-1H-isoquinoline 的衍生物。
• Novel and efficient synthesis of triazolobenzodiazepine analogues through the sequential Ugi 4CR-click-N-arylation reactions
  作者：Mohammad Sadegh Asgari、Mehdi Soheilizad、Parviz Rashidi Ranjbar、Bagher Larijani、Rahmatollah Rahimi、Mohammad Mahdavi

  DOI：10.1016/j.tetlet.2019.01.009

  日期：2019.2

  An efficient approach for the synthesis of N-alkyl-2-aryl-2-(6-oxo-4H-benzo[f][1,2,3]triazolol [1,5 -a][1,4]diazepin-5(6H)-yl)acetamides is described. The protocol involves Ugi four-component reaction of 2-bromobenzoic acid, propargylamine, aldehydes and isocyanides followed by in situ sequential click reaction of azide ion with triple bond and N-arylation reaction to afford desired products in good to excellent yields. (C) 2019 Elsevier Ltd. All rights reserved.
• Two-Step Synthesis of 2,3-Dihydropyrroles via a Formal 5-<i>endo</i> Cycloisomerization of Ugi 4-CR/Propargyl Adducts
  作者：Luis A. Polindara-García、Luis D. Miranda

  DOI：10.1021/ol3024727

  日期：2012.11.2

  A practical two-step synthesis of 2,3-dihydropyrroles from Ugi 4-CR/propargyl adducts is presented. The protocol includes a base-mediated formation of an allenamide functional group and an in situ metal-free formal 5-endo cycloisomerization that occurs in a highly regioselective manner at the allenamide C-gamma.