(Z)-2-benzoylamino-N-[(S)-1-(methoxycarbonyl)ethyl]-3-(1-naphthyl)-2-propenamide | 481061-40-9

• 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-benzoylamino-N-[(S)-1-(methoxycarbonyl)ethyl]-3-(1-naphthyl)-2-propenamide
• 英文别名: methyl (2S)-2-[[(Z)-2-benzamido-3-naphthalen-1-ylprop-2-enoyl]amino]propanoate
• CAS: 481061-40-9
• 化学式: C₂₄H₂₂N₂O₄
• 分子量: 402.45
• InChiKey: VTWAVLDHLGYUFZ-NOEYKIMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-2-benzoylamino-N-[(S)-1-(methoxycarbonyl)ethyl]-3-(1-naphthyl)-2-propenamide 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 (3R)-2-benzoylamino-3,4-dihydro-1-[(S)-(1-methoxycarbonyl)ethyl]-2(1H)-benzo[f]quinolinone 、 (3S)-2-benzoylamino-3,4-dihydro-1-[(S)-(1-methoxycarbonyl)ethyl]-2(1H)-benzo[f]quinolinone 、 (E)-2-benzoylamino-N-[(S)-1-(methoxycarbonyl)ethyl]-3-(1-naphthyl)-2-propenamide
  参考文献：
  名称：

  Asymmetric transformation of chiral auxiliary-substituted N-acyl-α-dehydro(1-naphthyl)alanines into 3,4-dihydrobenzo[f]quinolinone derivatives via photoinduced electron transfer

  摘要：

  Electron transfer-initiated photocyclizations of the title compounds [(Z)-1] with an (S)-alanine methyl ester auxiliary in methanol containing a tertiary amine were found to give (S,S)- and (R,S)-3,4-dihydrobenzo[f]quinolinones (2) as major products. The magnitude of diastereomeric excess (de) for (S,S)-2 was varied from 0 to 55%, depending on the properties of the amine and solvent employed. The mechanism of asymmetric induction in the photocyclization process eventually affording 2 was discussed based on solvent, tertiary amine and temperature effects on the de value. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.071
• 作为产物：
  描述：

  马尿酸 在 sodium acetate 、 乙酸酐 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 (Z)-2-benzoylamino-N-[(S)-1-(methoxycarbonyl)ethyl]-3-(1-naphthyl)-2-propenamide
  参考文献：
  名称：

  Asymmetric transformation of chiral auxiliary-substituted N-acyl-α-dehydro(1-naphthyl)alanines into 3,4-dihydrobenzo[f]quinolinone derivatives via photoinduced electron transfer

  摘要：

  Electron transfer-initiated photocyclizations of the title compounds [(Z)-1] with an (S)-alanine methyl ester auxiliary in methanol containing a tertiary amine were found to give (S,S)- and (R,S)-3,4-dihydrobenzo[f]quinolinones (2) as major products. The magnitude of diastereomeric excess (de) for (S,S)-2 was varied from 0 to 55%, depending on the properties of the amine and solvent employed. The mechanism of asymmetric induction in the photocyclization process eventually affording 2 was discussed based on solvent, tertiary amine and temperature effects on the de value. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.071

文献信息

• Maekawa, Kei; Igarashi, Tetsutaro; Kubo, Kanji, Heterocycles, 2002, vol. 57, # 9, p. 1591 - 1597
  作者：Maekawa, Kei、Igarashi, Tetsutaro、Kubo, Kanji、Sakurai, Tadamitsu

  DOI：——

  日期：——