N-[(E)-3-(methylamino)-3-oxo-1-phenanthren-9-ylprop-1-en-2-yl]benzamide | 1391158-10-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N-[(E)-3-(methylamino)-3-oxo-1-phenanthren-9-ylprop-1-en-2-yl]benzamide
• CAS: 1391158-10-3
• 化学式: C₂₅H₂₀N₂O₂
• 分子量: 380.446
• InChiKey: APVRRRQHAQCGCG-XQNSMLJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  9-甲醛菲 在 sodium acetate 、 乙酸酐 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.17h， 生成 N-[(E)-3-(methylamino)-3-oxo-1-phenanthren-9-ylprop-1-en-2-yl]benzamide
  参考文献：
  名称：

  Photoinduced Selective Transformation of N-Acyl-α-dehydro(9-phenanthryl)alaninamides into Their Cyclization Intermediates in a Polar Protic Solvent

  摘要：

  Irradiation of the title compounds [(Z)-1] in methanol afforded trans-3,8a-dihydro-2-dibenzo[f,h]quinolinone derivatives (trans-2) in preference to cis-2, all of which serve as precursors of the corresponding 3,4-dihydrodibenzoquinolinones. An analysis of the substituent and solvent effects on the cyclization occuring from the excited-state (E)-1 showed that the reactivity of this (E)-isomer is greatly influenced by the steric bulk of the alkyl group attached to the N'-amide nitrogen of the starting 1. In addition, this analysis confirmed that the stabilization of the excited-state (E)-1 (having a zwitterionic structure), by hydrogen-bonding and charge-transfer interactions with methanol, is an essential prerequisite for the occurrence of the photocyclization reaction selectively forming trans-2 and cis-2.

  DOI：

  10.3987/com-12-12449

文献信息

• Photoinduced Selective Transformation of N-Acyl-α-dehydro(9-phenanthryl)alaninamides into Their Cyclization Intermediates in a Polar Protic Solvent
  作者：Tadamitsu Sakurai、Yuki Kawanishi、Hiroko Yoshiie、Tetsutaro Igarashi

  DOI：10.3987/com-12-12449

  日期：——

  Irradiation of the title compounds [(Z)-1] in methanol afforded trans-3,8a-dihydro-2-dibenzo[f,h]quinolinone derivatives (trans-2) in preference to cis-2, all of which serve as precursors of the corresponding 3,4-dihydrodibenzoquinolinones. An analysis of the substituent and solvent effects on the cyclization occuring from the excited-state (E)-1 showed that the reactivity of this (E)-isomer is greatly influenced by the steric bulk of the alkyl group attached to the N'-amide nitrogen of the starting 1. In addition, this analysis confirmed that the stabilization of the excited-state (E)-1 (having a zwitterionic structure), by hydrogen-bonding and charge-transfer interactions with methanol, is an essential prerequisite for the occurrence of the photocyclization reaction selectively forming trans-2 and cis-2.