(Z)-2-acetylamino-3-(1-naphthyl)-N-phenyl-2-propenamide | 261916-35-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-2-acetylamino-3-(1-naphthyl)-N-phenyl-2-propenamide
• 英文别名: (Z)-2-acetamido-3-naphthalen-1-yl-N-phenylprop-2-enamide
• CAS: 261916-35-2
• 化学式: C₂₁H₁₈N₂O₂
• 分子量: 330.386
• InChiKey: SSDYJHBJBCTEIT-ZHZULCJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-2-acetylamino-3-(1-naphthyl)-N-phenyl-2-propenamide 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以38.6%的产率得到(E)-2-acetylamino-3-(1-naphthyl)-N-phenyl-2-propenamide
  参考文献：
  名称：

  Electron Transfer-initiated Photocyclization of Substituted a-Dehydro(1-naphthyl)alanines

  摘要：

  On irradiation in the presence of triethylamine, the title compounds (1) having n-butyl and benzyl groups gave preferentially dihydrobenzoquinolinones (2) via electron transfer, whereas the introduction of the bulky tert-butyl and phenyl substituents into 1 resulted in the formation of benzoisoquinoline (3) and 1-azetine (4) derivatives without affording 2.

  DOI：

  10.3987/com-99-8778
• 作为产物：
  描述：

  2-methyl-4-(1-naphthyl)methylidene-5-oxazolone 生成 (Z)-2-acetylamino-3-(1-naphthyl)-N-phenyl-2-propenamide
  参考文献：
  名称：

  Electron Transfer-initiated Photocyclization of Substituted a-Dehydro(1-naphthyl)alanines

  摘要：

  On irradiation in the presence of triethylamine, the title compounds (1) having n-butyl and benzyl groups gave preferentially dihydrobenzoquinolinones (2) via electron transfer, whereas the introduction of the bulky tert-butyl and phenyl substituents into 1 resulted in the formation of benzoisoquinoline (3) and 1-azetine (4) derivatives without affording 2.

  DOI：

  10.3987/com-99-8778

文献信息

• Electron transfer-initiated photocyclization of substituted N-acetyl-α-dehydro(1-naphthyl)alanines to 1,2-dihydrobenzo[f]quinolinone derivatives: scope and limitations
  作者：Kei Maekawa、Tetsutaro Igarashi、Kanji Kubo、Tadamitsu Sakurai

  DOI：10.1016/s0040-4020(01)00477-x

  日期：2001.6

  The irradiation of substituted N-acetyl-alpha -dehydro(1-naphthyl)alanines (1) in MeOH containing triethylamine with Pyrex-filtered light gave 1,2-dihydrobenzo[f]quinolinones (2) in preference to benzo[f]isoquinolines (3) and 1-azetines (4). Analysis of substituent effects on the product compositions revealed that the selectivity of 2 has a strong tendency to decrease with increasing steric bulkiness of the alkyl substituent introduced into the starting (Z)-1. From control and fluorescence quenching experiments it was shown that the photocyclization reaction of 1 affording 2 proceeds by an electron-transfer mechanism. The mechanism of this novel cyclization was discussed mainly based on substituent and solvent effects on both the reactivities of the excited singlet-state 1 and the selectivities of the products 2-4. (C) 2001 Elsevier Science Ltd. All rights reserved.