(Z)-2-(3-benzyl-5-methyl-1,2,4-triazol-4-yl)-3-(1-naphthyl)-2-propeonic acid | 1118428-71-9

• 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)-2-(3-benzyl-5-methyl-1,2,4-triazol-4-yl)-3-(1-naphthyl)-2-propeonic acid
• 英文别名: (Z)-2-(3-benzyl-5-methyl-1,2,4-triazol-4-yl)-3-naphthalen-1-ylprop-2-enoic acid
• CAS: 1118428-71-9
• 化学式: C₂₃H₁₉N₃O₂
• 分子量: 369.423
• InChiKey: ZXIBZIFWAIBJCO-QNGOZBTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  68
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-2-(3-benzyl-5-methyl-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)-2-(3-benzyl-5-methyl-1,2,4-triazol-4-yl)-N-methyl-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
• 作为产物：
  描述：

  (Z)-2-methyl-4-(1-naphthylmethylene)-5(4H)-oxazolone 、 苯乙酸肼 以 乙腈 为溶剂， 生成 (Z)-2-(3-benzyl-5-methyl-1,2,4-triazol-4-yl)-3-(1-naphthyl)-2-propeonic acid
  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

• Efficient Formation of a Triazole Ring via Novel Ring-Opening Reaction of (Z)-2-Methyl-4-arylmethylene-5(4H)-oxazolones with Hydrazides
  作者：Tadamitsu Sakurai、Kei Maekawa、Atsushi Tomoda、Tetsutaro Igarashi

  DOI：10.3987/com-08-11457

  日期：——

  mechanistic points of view. It was found that the novel ring-opening reaction proceeded to give (Z)-2-(3-methyl-5-substituted 1,2,4-triazol-4-yl)-3-aryl-2-propenoic acids (1,2,4-triazole-substituted (Z)-α-dehydroarylalanines| as major products, along with minor or negligible amounts of their isomers. Substituent and solvent effects on the relative composition of these two isomers confirmed that this

  从合成和机理的角度研究了标题恶唑酮与酰肼亲核试剂的开环模式。发现新的开环反应进行得到（Z）-2-（3-甲基-5-取代的1,2,4-三唑-4-基）-3-芳基-2-丙烯酸（1 ,2,4-三唑取代的 (Z)-α-脱氢芳基丙氨酸|作为主要产物，以及少量或可忽略不计的异构体。取代基和溶剂对这两种异构体的相对组成的影响证实了该组成取决于空间位阻芳基（在恶唑酮中）和酰基（在酰肼亲核试剂中）取代基以及溶剂极性的电子因素。