N-(4-methoxybenzyl)-2-cyano-3-(dimethylamino)-N-phenylacrylamide | 1309579-08-5

• 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-(4-methoxybenzyl)-2-cyano-3-(dimethylamino)-N-phenylacrylamide
• CAS: 1309579-08-5
• 化学式: C₂₀H₂₁N₃O₂
• 分子量: 335.406
• InChiKey: PZCLXHSZGWBISP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  56.57
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(4-methoxybenzyl)-2-cyano-3-(dimethylamino)-N-phenylacrylamide 在 三氟乙酸酐 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以95%的产率得到1-(4-methoxybenzyl)-1,2-dihydro-4-hydroxy-2-oxoquinoline-3-carbaldehyde
  参考文献：
  名称：

  α-Dimethylaminomethylenation-induced Houben–Hoesch-type cyclization of cyanoacetanilides: a practical synthesis of 3-formyl-4-hydroxyquinolin-2(1H)-ones

  摘要：

  The tandem reaction of cyanoacetanilides with triflic anhydride in DMF proceeded at room temperature to afford 3-formyl-4-hydroxyquinolin-2(1H)-ones in good to high yields. A detailed mechanistic study revealed that the tandem reaction proceeded via alpha-dimethylaminomethylenation, which promoted the subsequent Houben-Hoesch-type cyclization. Both alpha-functionalization and the cyclization steps were optimized, and a multi-gram scale synthesis of 3-formyl-4-hydroxyquinolin-2(1H)-one was achieved. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.040
• 作为产物：
  描述：

  2-cyano-N-(4-methoxybenzyl)-N-phenylacetamide 、 N,N-二甲基甲酰胺二甲基缩醛 以 甲苯 为溶剂， 以62%的产率得到N-(4-methoxybenzyl)-2-cyano-3-(dimethylamino)-N-phenylacrylamide
  参考文献：
  名称：

  α-Dimethylaminomethylenation-induced Houben–Hoesch-type cyclization of cyanoacetanilides: a practical synthesis of 3-formyl-4-hydroxyquinolin-2(1H)-ones

  摘要：

  The tandem reaction of cyanoacetanilides with triflic anhydride in DMF proceeded at room temperature to afford 3-formyl-4-hydroxyquinolin-2(1H)-ones in good to high yields. A detailed mechanistic study revealed that the tandem reaction proceeded via alpha-dimethylaminomethylenation, which promoted the subsequent Houben-Hoesch-type cyclization. Both alpha-functionalization and the cyclization steps were optimized, and a multi-gram scale synthesis of 3-formyl-4-hydroxyquinolin-2(1H)-one was achieved. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.040

文献信息

• α-Dimethylaminomethylenation-induced Houben–Hoesch-type cyclization of cyanoacetanilides: a practical synthesis of 3-formyl-4-hydroxyquinolin-2(1H)-ones
  作者：Yusuke Kobayashi、Terue Nakatani、Rie Tanaka、Mari Okada、Eri Torii、Takashi Harayama、Tetsutaro Kimachi

  DOI：10.1016/j.tet.2011.03.040

  日期：2011.5

  The tandem reaction of cyanoacetanilides with triflic anhydride in DMF proceeded at room temperature to afford 3-formyl-4-hydroxyquinolin-2(1H)-ones in good to high yields. A detailed mechanistic study revealed that the tandem reaction proceeded via alpha-dimethylaminomethylenation, which promoted the subsequent Houben-Hoesch-type cyclization. Both alpha-functionalization and the cyclization steps were optimized, and a multi-gram scale synthesis of 3-formyl-4-hydroxyquinolin-2(1H)-one was achieved. (C) 2011 Elsevier Ltd. All rights reserved.