trans-N-{2-[2-phenylethenyl]phenyl}aminoacetic acid | 1260104-32-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: trans-N-{2-[2-phenylethenyl]phenyl}aminoacetic acid
• 英文别名: 2-[2-[(E)-2-phenylethenyl]anilino]acetic acid
• CAS: 1260104-32-2
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: ABQOUQKHOLIRAP-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-N-{2-[2-phenylethenyl]phenyl}aminoacetic acid 在 sodium nitrite 、 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Synthesis and photochemistry of 3-(o-stilbeneyl)-4-H/Me/Ph-sydnones; intramolecular cyclization to 1,2-benzodiazepines and/or quinolines

  摘要：

  Stilbeneylsydnone derivatives were synthesized by a sequence of reactions in good yields. Irradiation of 3-stilbeneyl-4-methylsydnone 4 gives 1H-1,2-benzodiazepine derivative 7 as the main product along with 2-methylquinoline derivative 20. Irradiation of 3-stilbeneyl-4-phenylsydnone 5 afforded only 1H-1,2-benzodiazepine derivative 8 whereas on irradiation of 4-unsubstituted 3-stilbeneylsydnone 3 no benzodiazepine derivative was detected. An efficient novel photochemical approach to 1H-1,2-benzo-diazepines has been found from the new 3-(o-stilbeneyl)-4-substituted-sydnones via intramolecular 1,7-electrocyclization reaction of the photogenerated nitrile imines. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.013
• 作为产物：
  描述：

  trans-ethyl N-{2-[2-phenylethenyl]phenyl}aminoacetate 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 以77.2%的产率得到trans-N-{2-[2-phenylethenyl]phenyl}aminoacetic acid
  参考文献：
  名称：

  Synthesis and photochemistry of 3-(o-stilbeneyl)-4-H/Me/Ph-sydnones; intramolecular cyclization to 1,2-benzodiazepines and/or quinolines

  摘要：

  Stilbeneylsydnone derivatives were synthesized by a sequence of reactions in good yields. Irradiation of 3-stilbeneyl-4-methylsydnone 4 gives 1H-1,2-benzodiazepine derivative 7 as the main product along with 2-methylquinoline derivative 20. Irradiation of 3-stilbeneyl-4-phenylsydnone 5 afforded only 1H-1,2-benzodiazepine derivative 8 whereas on irradiation of 4-unsubstituted 3-stilbeneylsydnone 3 no benzodiazepine derivative was detected. An efficient novel photochemical approach to 1H-1,2-benzo-diazepines has been found from the new 3-(o-stilbeneyl)-4-substituted-sydnones via intramolecular 1,7-electrocyclization reaction of the photogenerated nitrile imines. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.013

文献信息

• Synthesis and photochemistry of 3-(o-stilbeneyl)-4-H/Me/Ph-sydnones; intramolecular cyclization to 1,2-benzodiazepines and/or quinolines
  作者：Kristina Butković、Dragana Vuk、Željko Marinić、Josip Penić、Marija Šindler-Kulyk

  DOI：10.1016/j.tet.2010.10.013

  日期：2010.11

  Stilbeneylsydnone derivatives were synthesized by a sequence of reactions in good yields. Irradiation of 3-stilbeneyl-4-methylsydnone 4 gives 1H-1,2-benzodiazepine derivative 7 as the main product along with 2-methylquinoline derivative 20. Irradiation of 3-stilbeneyl-4-phenylsydnone 5 afforded only 1H-1,2-benzodiazepine derivative 8 whereas on irradiation of 4-unsubstituted 3-stilbeneylsydnone 3 no benzodiazepine derivative was detected. An efficient novel photochemical approach to 1H-1,2-benzo-diazepines has been found from the new 3-(o-stilbeneyl)-4-substituted-sydnones via intramolecular 1,7-electrocyclization reaction of the photogenerated nitrile imines. (C) 2010 Elsevier Ltd. All rights reserved.