1-[3,3-dimethyl-2-oxo-1-(p-tolyl)azetidin-4-yl]-2-[(Z)-3,3-dimethyl-2-oxo-1-(p-tolyl)azetidin-4-ylidene]-5-fluoro-3-(p-fluorophenylimino)-2,3-dihydroindole | 935756-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1-[3,3-dimethyl-2-oxo-1-(p-tolyl)azetidin-4-yl]-2-[(Z)-3,3-dimethyl-2-oxo-1-(p-tolyl)azetidin-4-ylidene]-5-fluoro-3-(p-fluorophenylimino)-2,3-dihydroindole
• CAS: 935756-08-4
• 化学式: C₃₈H₃₄F₂N₄O₂
• 分子量: 616.71
• InChiKey: NQWJLDLMHFRJKR-BIRHQSHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.21
• 重原子数：
  46.0
• 可旋转键数：
  4.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  56.22
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-[3,3-dimethyl-2-oxo-1-(p-tolyl)azetidin-4-yl]-2-[(Z)-3,3-dimethyl-2-oxo-1-(p-tolyl)azetidin-4-ylidene]-5-fluoro-3-(p-fluorophenylimino)-2,3-dihydroindole 在 对甲苯磺酸 作用下， 以 1,1,2-三氯乙烷 为溶剂， 反应 4.0h， 以83%的产率得到8-fluoro-1-(p-fluorophenyl)-3,3-dimethyl-δ-carboline-2,4-dione
  参考文献：
  名称：

  Interaction of β-Lactam Carbenes with Aryl Isonitriles:  An Unprecedented Rearrangement of 2-Azetidinonylidene Indoles to δ-Carbolinones

  摘要：

  The reaction of, beta-lactam carbenes with aryl isonitriles proceeded in a novel [2 + 2] fashion to give high yields of 2-azetidinonylidene indoles 4, which underwent an unprecedented rearrangement to furnish 4-arylimino-delta-carbolin-2-ones 5 in almost quantitative yields. Acid catalyzed rearrangement and the subsequent hydrolysis of 2-azetidinonylidene indoles 4 produced two types of delta-carbolin-2,4-diones 10 and 11, respectively, in good to excellent yields. The photophysical study showed that both delta-carbolin-2,4-diones 10 and 11 are highly fluorescent with the fluorescent quantum yields being up to 0.43.

  DOI：

  10.1021/jo0700631
• 作为产物：
  描述：

  1,7,8-triaza-3,3,6,6-tetramethyl-5-oxa-2-oxo-1-(p-methylphenyl)spiro[3,4]oct-7-ene 、 4-氟苯基异氰酸酯 以 1,4-二氧六环 为溶剂， 反应 11.0h， 以74%的产率得到1-[3,3-dimethyl-2-oxo-1-(p-tolyl)azetidin-4-yl]-2-[(Z)-3,3-dimethyl-2-oxo-1-(p-tolyl)azetidin-4-ylidene]-5-fluoro-3-(p-fluorophenylimino)-2,3-dihydroindole
  参考文献：
  名称：

  Interaction of β-Lactam Carbenes with Aryl Isonitriles:  An Unprecedented Rearrangement of 2-Azetidinonylidene Indoles to δ-Carbolinones

  摘要：

  The reaction of, beta-lactam carbenes with aryl isonitriles proceeded in a novel [2 + 2] fashion to give high yields of 2-azetidinonylidene indoles 4, which underwent an unprecedented rearrangement to furnish 4-arylimino-delta-carbolin-2-ones 5 in almost quantitative yields. Acid catalyzed rearrangement and the subsequent hydrolysis of 2-azetidinonylidene indoles 4 produced two types of delta-carbolin-2,4-diones 10 and 11, respectively, in good to excellent yields. The photophysical study showed that both delta-carbolin-2,4-diones 10 and 11 are highly fluorescent with the fluorescent quantum yields being up to 0.43.

  DOI：

  10.1021/jo0700631