(Z)-2-acetylamino-N-methyl-3-(1-naphthyl)-2-propenamide | 360078-83-7

• 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-N-methyl-3-(1-naphthyl)-2-propenamide
• 英文别名: (Z)-2-acetamido-N-methyl-3-naphthalen-1-ylprop-2-enamide
• CAS: 360078-83-7
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: PQMHPTQJNDJIFV-GDNBJRDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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-N-methyl-3-(1-naphthyl)-2-propenamide 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 1-methyl-3-methylaminocarbonylbenzo[f]isoquinoline 、 (E)-2-acetylamino-N-methyl-3-(1-naphthyl)-2-propenamide 、 3-acetylamino-3,4-dihydro-1-methyl-2(1H)-benzo[f]quinolinone
  参考文献：
  名称：

  Electron transfer-initiated photocyclization of substituted N-acetyl-α-dehydro(1-naphthyl)alanines to 1,2-dihydrobenzo[f]quinolinone derivatives: scope and limitations

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)00477-x
• 作为产物：
  描述：

  1-萘甲醛 在 sodium acetate 、 乙酸酐 作用下， 以 氯仿 为溶剂， 反应 7.0h， 生成 (Z)-2-acetylamino-N-methyl-3-(1-naphthyl)-2-propenamide
  参考文献：
  名称：

  Electron transfer-initiated photocyclization of substituted N-acetyl-α-dehydro(1-naphthyl)alanines to 1,2-dihydrobenzo[f]quinolinone derivatives: scope and limitations

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)00477-x

文献信息

• Maekawa, Kei; Kajiwara, Hiroo; Iseya, Yoshiyuki, Heterocycles, 2003, vol. 60, # 3, p. 637 - 654
  作者：Maekawa, Kei、Kajiwara, Hiroo、Iseya, Yoshiyuki、Igarashi, Tetsutaro、Sakurai, Tadamitsu

  DOI：——

  日期：——
• Asymmetric Photocyclization Reactions of N-Acetyl-α-dehydro(1-naphthyl)alaninamides in the Presence of Chiral Amine
  作者：Tadamitsu Sakurai、Kei Maekawa、Toshiyuki Tanami、Tetsutaro Igarashi

  DOI：10.3987/com-11-12265

  日期：——

  Irradiation of the title compound having an N'-methyl group in 2-propanol and dichloromethane containing (S)-1-methyl-2-pyrrolidinemethanol at room temperature afforded (R)-3,4-dihydrobenzo[f]quinolinone derivative in enantiomeric excesses (ee's) of 7 and 30%, respectively. On the other hand, the corresponding (S)-enantiomer was obtained in 21-23% ee's on room temperature irradiation in the above solvents containing (S)-nicotine which enhanced these ee values up to 34-59% at 78 degrees C.