(Z)-2-acetylamino-N-butyl-3-(1-naphthyl)-2-propenamide | 261916-28-3

• 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-butyl-3-(1-naphthyl)-2-propenamide
• 英文别名: (Z)-2-acetamido-N-butyl-3-naphthalen-1-ylprop-2-enamide
• CAS: 261916-28-3
• 化学式: C₁₉H₂₂N₂O₂
• 分子量: 310.396
• InChiKey: MSXYQAFEYNWIMI-AQTBWJFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  苯胺 、 (Z)-2-acetylamino-N-butyl-3-(1-naphthyl)-2-propenamide 以100%的产率得到(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
• 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-butyl-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

• A novel route to 2-imidazolin-5-one derivatives via oxidative cyclization of aryl-substituted (Z)-N-acetyl-α-dehydroalanines having a dialkylamino group
  作者：Atsushi Kawasaki、Kei Maekawa、Kanji Kubo、Tetsutaro Igarashi、Tadamitsu Sakurai

  DOI：10.1016/j.tet.2004.07.068

  日期：2004.10

  It was found that the reaction of the title compounds [(Z)-1] with oxygen in methanol proceeds according to the first-order kinetics to give (Z)-2-imidazolin-5-one derivatives and hydrogen peroxide in quantitative yields. Analysis of substituent and solvent effects on the rate constant for this oxidative cyclization led us to propose that electron transfer from the dialkylamino nitrogen in (Z)-1 to

  发现标题化合物[（Z）-1 ]与氧气在甲醇中的反应根据一级动力学进行，以定量产率得到（Z）-2-咪唑啉-5-酮衍生物和过氧化氢。分析取代基和溶剂对这种氧化环化反应的速率常数的影响，导致我们提出电子从（Z）-1中的二烷基氨基氮转移到氧，超氧化物提取酰胺-质子以及随后的分子内电子转移都是-确定步骤。讨论了芳基取代的（Z）-N-乙酰基-α-脱氢丙氨酸衍生物新型环化反应的合成实用性。
• Motohashi, Toyohisa; Maekawa, Kei; Kubo, Kanji, Heterocycles, 2002, vol. 57, # 2, p. 269 - 292
  作者：Motohashi, Toyohisa、Maekawa, Kei、Kubo, Kanji、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.
• 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.
• Electron Transfer-initiated Photocyclization of Substituted a-Dehydro(1-naphthyl)alanines
  作者：Tadamitsu Sakurai、Yoshiko Morioka、Kei Maekawa、Kanji Kubo

  DOI：10.3987/com-99-8778

  日期：——

  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.