(Z)-N-methyl-2-(3-methyl-5-phenyl-1,2,4-triazol-4-yl)-3-naphthalen-1-ylprop-2-enamide | 1147293-01-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-N-methyl-2-(3-methyl-5-phenyl-1,2,4-triazol-4-yl)-3-naphthalen-1-ylprop-2-enamide
• CAS: 1147293-01-3
• 化学式: C₂₃H₂₀N₄O
• 分子量: 368.438
• InChiKey: RIJGPZPROVTBTI-QNGOZBTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  (Z)-N-methyl-2-(3-methyl-5-phenyl-1,2,4-triazol-4-yl)-3-naphthalen-1-ylprop-2-enamide 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 4-Methyl-2-(3-methyl-5-phenyl-1,2,4-triazol-4-yl)-1,2-dihydrobenzo[f]quinolin-3-one 、 4-methyl-3(4H)-benzoquinolinone
  参考文献：
  名称：

  Novel Photoinduced Electorn Transfer-Initiated Cyclization of 1,2,4-Triazole-Substituted α-Dehydronaphthylalaninamides in the Presence of Triethylamine

  摘要：

  The irradiation of the title compounds [(Z)-1] in nitrogen-saturated methanol containing triethylamine (TEA) at room temperature was found to quantitatively afford 2(1H)-benzo/[f]quinolinone (2) and 3,4-dihydro-3-(3-methyl-5-substituted 1,2,4-triazol-4-yl)-2(1H)-benzo[f]quinolinone (3) derivatives, which were described as being formed via electron transfer from TEA to the excited-state (E)-1. Analysis of solvent and substituent effects on the composition ratio of 2 to 3 confirmed that this ratio is increased from 0.2 to 9.0 with an increase in the proton-donating ability and polarity of solvent as well as in the electron-withdrawing ability of substituent bonded to the triazole ring.

  DOI：

  10.3987/com-08-s(f)53
• 作为产物：
  描述：

  (Z)-2-(3-methyl-5-phenyl-1,2,4-triazol-4-yl)-3-(1-naphthyl)-2-propeonic acid 、 甲胺 以 1,4-二氧六环 为溶剂， 生成 (Z)-N-methyl-2-(3-methyl-5-phenyl-1,2,4-triazol-4-yl)-3-naphthalen-1-ylprop-2-enamide
  参考文献：
  名称：

  Novel Photoinduced Electorn Transfer-Initiated Cyclization of 1,2,4-Triazole-Substituted α-Dehydronaphthylalaninamides in the Presence of Triethylamine

  摘要：

  The irradiation of the title compounds [(Z)-1] in nitrogen-saturated methanol containing triethylamine (TEA) at room temperature was found to quantitatively afford 2(1H)-benzo/[f]quinolinone (2) and 3,4-dihydro-3-(3-methyl-5-substituted 1,2,4-triazol-4-yl)-2(1H)-benzo[f]quinolinone (3) derivatives, which were described as being formed via electron transfer from TEA to the excited-state (E)-1. Analysis of solvent and substituent effects on the composition ratio of 2 to 3 confirmed that this ratio is increased from 0.2 to 9.0 with an increase in the proton-donating ability and polarity of solvent as well as in the electron-withdrawing ability of substituent bonded to the triazole ring.

  DOI：

  10.3987/com-08-s(f)53

文献信息

• Substituent Effects on the Electron Transfer-Initiated Photochemical Transformation of 1,2,4-Triazole-Substituted α-Dehydroarylalaninamides into 2(1H)-Quinolinone Derivatives
  作者：Tadamitsu Sakurai、Yuichi Yazawa、Minoru Suzuki、Tetsutaro Igarashi

  DOI：10.3987/com-09-s(s)55

  日期：——

  An investigation was undertaken to elucidate substituent effects on the photoreactivity of 1,2,4-triazole-substituted alpha-dehydroarylalaninamides [(Z)-1] as well as on the selectivity of 2(1H)-quinolinone derivatives (2) from a synthetic point of view. It was found that photoinduced electron transfer-initiated cyclization of (Z)-1 bearing a meta-substituted phenyl or a 4-substituted naphthalen-1-yl group in methanol proceeds with a moderate to good efficiency affording the corresponding product 2 in a selectivity ranging from 33 to 100%.
• Novel Photoinduced Electorn Transfer-Initiated Cyclization of 1,2,4-Triazole-Substituted α-Dehydronaphthylalaninamides in the Presence of Triethylamine
  作者：Tadamitsu Sakurai、Kei Maekawa、Atsushi Tomoda、Tetsutaro Igarashi

  DOI：10.3987/com-08-s(f)53

  日期：——

  The irradiation of the title compounds [(Z)-1] in nitrogen-saturated methanol containing triethylamine (TEA) at room temperature was found to quantitatively afford 2(1H)-benzo/[f]quinolinone (2) and 3,4-dihydro-3-(3-methyl-5-substituted 1,2,4-triazol-4-yl)-2(1H)-benzo[f]quinolinone (3) derivatives, which were described as being formed via electron transfer from TEA to the excited-state (E)-1. Analysis of solvent and substituent effects on the composition ratio of 2 to 3 confirmed that this ratio is increased from 0.2 to 9.0 with an increase in the proton-donating ability and polarity of solvent as well as in the electron-withdrawing ability of substituent bonded to the triazole ring.