(Z)-N-methyl-3-(1-naphthyl)-2-(4-trifluoromethylbenzoylamino)-2-propenamide | 800393-90-2

• 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: (Z)-N-methyl-3-(1-naphthyl)-2-(4-trifluoromethylbenzoylamino)-2-propenamide
• 英文别名: N-[(Z)-3-(methylamino)-1-naphthalen-1-yl-3-oxoprop-1-en-2-yl]-4-(trifluoromethyl)benzamide
• CAS: 800393-90-2
• 化学式: C₂₂H₁₇F₃N₂O₂
• 分子量: 398.384
• InChiKey: PTPOLYIBXXOHCW-UYRXBGFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-N-methyl-3-(1-naphthyl)-2-(4-trifluoromethylbenzoylamino)-2-propenamide 在 TEA 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以75%的产率得到3,4-dihydro-1-methyl-3-(4-trifluoromethylbenzoylamino)-2(1H)-benzo[f]quinolinone
  参考文献：
  名称：

  Highly selective conversion of N-aroyl-α-dehydronaphthylalaninamides into 3,4-dihydrobenzoquinolinone derivatives via photoinduced intermolecular electron transfer

  摘要：

  The irradiation of substituted (Z)-N-aroyl-alpha-dehydronaphthylalaninamides [(Z)-1] in methanol containing triethylamine (TEA) with Pyrex-filtered light was found to give 3,4-dihydrobenzoquinolinone derivatives (2) in high yields along with minor amounts of 4,5-dihydrooxazole derivatives (3). Analysis of the substituent effects on product composition revealed that both the photoreactivity of 1 and the selectivity of 2 are decreased with increasing electron-withdrawing ability of the substituent introduced at the para-position on the N-benzoyl benzene ring. From the analysis of the dependence of the quantum yield for the formation of 2 on the TEA concentration, it was found that back electron transfer occurs efficiently within an (E)-1 anion radical-TEA cation radical pair intermediate. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.096
• 作为产物：
  描述：

  N-[4-(三氟甲基)苯甲酰基]甘氨酸 在 sodium acetate 、 乙酸酐 作用下， 以 氯仿 为溶剂， 生成 (Z)-N-methyl-3-(1-naphthyl)-2-(4-trifluoromethylbenzoylamino)-2-propenamide
  参考文献：
  名称：

  Highly selective conversion of N-aroyl-α-dehydronaphthylalaninamides into 3,4-dihydrobenzoquinolinone derivatives via photoinduced intermolecular electron transfer

  摘要：

  The irradiation of substituted (Z)-N-aroyl-alpha-dehydronaphthylalaninamides [(Z)-1] in methanol containing triethylamine (TEA) with Pyrex-filtered light was found to give 3,4-dihydrobenzoquinolinone derivatives (2) in high yields along with minor amounts of 4,5-dihydrooxazole derivatives (3). Analysis of the substituent effects on product composition revealed that both the photoreactivity of 1 and the selectivity of 2 are decreased with increasing electron-withdrawing ability of the substituent introduced at the para-position on the N-benzoyl benzene ring. From the analysis of the dependence of the quantum yield for the formation of 2 on the TEA concentration, it was found that back electron transfer occurs efficiently within an (E)-1 anion radical-TEA cation radical pair intermediate. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.096

文献信息

• Highly selective conversion of N-aroyl-α-dehydronaphthylalaninamides into 3,4-dihydrobenzoquinolinone derivatives via photoinduced intermolecular electron transfer
  作者：Kei Maekawa、Ayana Shinozuka、Michiko Naito、Tetsutaro Igarashi、Tadamitsu Sakurai

  DOI：10.1016/j.tet.2004.08.096

  日期：2004.11

  The irradiation of substituted (Z)-N-aroyl-alpha-dehydronaphthylalaninamides [(Z)-1] in methanol containing triethylamine (TEA) with Pyrex-filtered light was found to give 3,4-dihydrobenzoquinolinone derivatives (2) in high yields along with minor amounts of 4,5-dihydrooxazole derivatives (3). Analysis of the substituent effects on product composition revealed that both the photoreactivity of 1 and the selectivity of 2 are decreased with increasing electron-withdrawing ability of the substituent introduced at the para-position on the N-benzoyl benzene ring. From the analysis of the dependence of the quantum yield for the formation of 2 on the TEA concentration, it was found that back electron transfer occurs efficiently within an (E)-1 anion radical-TEA cation radical pair intermediate. (C) 2004 Elsevier Ltd. All rights reserved.