N-[(3S,12bS)-1-methyl-2-oxo-3,12b-dihydrophenanthro[9,10-b]pyridin-3-yl]benzamide | 1450838-25-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-[(3S,12bS)-1-methyl-2-oxo-3,12b-dihydrophenanthro[9,10-b]pyridin-3-yl]benzamide
• CAS: 1450838-25-1
• 化学式: C₂₅H₂₀N₂O₂
• 分子量: 380.446
• InChiKey: XDRQKUDRQPVUAJ-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[(3S,12bS)-1-methyl-2-oxo-3,12b-dihydrophenanthro[9,10-b]pyridin-3-yl]benzamide 以 甲醇 为溶剂， 生成 3-benzoylamino-3,8a-dihydro-1-methyl-2(1H)-dibenzo[f,h]quinolinone
  参考文献：
  名称：

  Asymmetric Conversion of (Z)-N-Benzoyl-α-dehydro(9-phenanthryl)alanine N´-Methylamide into Its Cyclization Intermediates via Photoinduced Electron Transfer

  摘要：

  Irradiation of (Z)-N-benzoyl-alpha-dehydro(9-phenanthryl)alanine N'-methylamide [(Z)-1] in 2-propanol-methanol (4:1 v/v) containing (S)-nicotine afforded the (3S,8aS)-3,8a-dihydrodibenzo[f,h]quinolinone derivative [(3S,8aS)-2] and (3R,8aS)-2 in 20% and 35% enantiomeric excess (ee), respectively. Analysis of the effects of a chiral amine and solvent on the electron transfer-initiated enantioselective photocyclization of (Z)-1 revealed that the magnitude of the ee is predominantly determined by the ability of this amine to form hydrogen bonds at the two sites of the enol intermediate as the precursor of 2.

  DOI：

  10.3987/com-13-12724
• 作为产物：
  描述：

  (Z)-N-benzoyl-α-dehydro(9-phenanthryl)alanine N'-methylamide 在 烟碱 作用下， 以 甲醇 、 异丙醇 为溶剂， 以20%的产率得到
  参考文献：
  名称：

  Asymmetric Conversion of (Z)-N-Benzoyl-α-dehydro(9-phenanthryl)alanine N´-Methylamide into Its Cyclization Intermediates via Photoinduced Electron Transfer

  摘要：

  Irradiation of (Z)-N-benzoyl-alpha-dehydro(9-phenanthryl)alanine N'-methylamide [(Z)-1] in 2-propanol-methanol (4:1 v/v) containing (S)-nicotine afforded the (3S,8aS)-3,8a-dihydrodibenzo[f,h]quinolinone derivative [(3S,8aS)-2] and (3R,8aS)-2 in 20% and 35% enantiomeric excess (ee), respectively. Analysis of the effects of a chiral amine and solvent on the electron transfer-initiated enantioselective photocyclization of (Z)-1 revealed that the magnitude of the ee is predominantly determined by the ability of this amine to form hydrogen bonds at the two sites of the enol intermediate as the precursor of 2.

  DOI：

  10.3987/com-13-12724

文献信息

• Asymmetric Conversion of (Z)-N-Benzoyl-α-dehydro(9-phenanthryl)alanine N´-Methylamide into Its Cyclization Intermediates via Photoinduced Electron Transfer
  作者：Tadamitsu Sakurai、Shin-ichi Matsuki、Kaoru Kawai、Tetsutaro Igarashi、Takayuki Kimura、Shinsaku Hattori

  DOI：10.3987/com-13-12724

  日期：——

  Irradiation of (Z)-N-benzoyl-alpha-dehydro(9-phenanthryl)alanine N'-methylamide [(Z)-1] in 2-propanol-methanol (4:1 v/v) containing (S)-nicotine afforded the (3S,8aS)-3,8a-dihydrodibenzo[f,h]quinolinone derivative [(3S,8aS)-2] and (3R,8aS)-2 in 20% and 35% enantiomeric excess (ee), respectively. Analysis of the effects of a chiral amine and solvent on the electron transfer-initiated enantioselective photocyclization of (Z)-1 revealed that the magnitude of the ee is predominantly determined by the ability of this amine to form hydrogen bonds at the two sites of the enol intermediate as the precursor of 2.