(E)-1-(indol-2-yl)-3-phenyl-2-propen-1-one | 364078-87-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (E)-1-(indol-2-yl)-3-phenyl-2-propen-1-one
• 英文别名: (E)-1-(1H-indol-2-yl)-3-phenylprop-2-en-1-one
• CAS: 364078-87-5
• 化学式: C₁₇H₁₃NO
• 分子量: 247.296
• InChiKey: VYQWXRMXYPMXCN-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-(indol-2-yl)-3-phenyl-2-propen-1-one 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以72%的产率得到1-phenyl-3-oxo-1,2,3,4-tetrahydrocyclopent[b]indole
  参考文献：
  名称：

  Reaction of 1-Benzenesulfonylindole-2,3-dicarboxylic Anhydride with Wittig Reagents: Synthesis of Pyrrolo[1,2-a]indoles and Cyclopent[b]indole

  摘要：

  Treatment of 1-benzenesulfonylindole-2,3-dicarboxylic anhydride with methylenetriphenylphosphorane gave the corresponding ylide. After esterification of the carboxyl group and removal of the benzenesulfonyl group of the ylide, the obtained ylide was reacted with aldehydes to yield alpha,beta -unsaturated ketones, which were converted to pyrrolo[1,2-a]indoles. We also examined the reactivity of the anhydride with (carbethoxymethylene)triphenylphosphorane and (carbethoxyethylidene)triphenylphosphorane.

  DOI：

  10.3987/com-01-9230
• 作为产物：
  描述：

  [2-(1-benzenesulfonyl-3-carboxyindol-2-yl)-1-ethoxycarbonyl-2-oxoethylidene]triphenylphosphorane 在 盐酸 、 sodium 作用下， 以 乙醇 、 均三甲苯 为溶剂， 反应 11.5h， 生成 (E)-1-(indol-2-yl)-3-phenyl-2-propen-1-one
  参考文献：
  名称：

  Reaction of 1-Benzenesulfonylindole-2,3-dicarboxylic Anhydride with Wittig Reagents: Synthesis of Pyrrolo[1,2-a]indoles and Cyclopent[b]indole

  摘要：

  Treatment of 1-benzenesulfonylindole-2,3-dicarboxylic anhydride with methylenetriphenylphosphorane gave the corresponding ylide. After esterification of the carboxyl group and removal of the benzenesulfonyl group of the ylide, the obtained ylide was reacted with aldehydes to yield alpha,beta -unsaturated ketones, which were converted to pyrrolo[1,2-a]indoles. We also examined the reactivity of the anhydride with (carbethoxymethylene)triphenylphosphorane and (carbethoxyethylidene)triphenylphosphorane.

  DOI：

  10.3987/com-01-9230

文献信息

• Palladium-Catalyzed Domino C,N-Coupling/Carbonylation/Suzuki Coupling Reaction: An Efficient Synthesis of 2-Aroyl-/Heteroaroylindoles
  作者：Martin Arthuis、Renée Pontikis、Jean-Claude Florent

  DOI：10.1021/ol901875z

  日期：2009.10.15

  A convenient one-pot synthesis of 2-aroylindoles using a domino palladium-catalyzed C,N-coupling/carbonylation/C,C-coupling sequence is described. The reaction involved easily prepared 2-gem-dibromovinylanilines and boronic acids under carbon monoxide. Optimized reaction conditions allowed the construction of a wide variety of highly functionalized 2-aroyl-/heteroaroylindoles in satisfactory yields

  描述了使用多米诺钯催化的C，N偶联/羰基化/ C，C偶联序列方便地一锅合成2-芳基吲哚。所涉及的反应容易地制备2-偕- dibromovinylanilines和硼酸下一氧化碳。优化的反应条件允许以令人满意的产率构建各种高度官能化的2-芳酰基-/杂芳酰基吲哚。
• Discovery of compounds that reactivate p53 mutants in vitro and in vivo
  作者：Geetha Durairaj、Özlem Demir、Bryant Lim、Roberta Baronio、Delia Tifrea、Linda V. Hall、Jacob C. DeForest、Linda Lauinger、Maryam M. Jebril Fallatah、Clinton Yu、Hosung Bae、Da-Wei Lin、Jin Kwang Kim、Faezeh Salehi、Cholsoon Jang、Feng Qiao、Richard H. Lathrop、Lan Huang、Robert Edwards、Scott Rychnovsky、Rommie E. Amaro、Peter Kaiser

  DOI：10.1016/j.chembiol.2022.07.003

  日期：2022.9
• Reaction of 1-Benzenesulfonylindole-2,3-dicarboxylic Anhydride with Wittig Reagents: Synthesis of Pyrrolo[1,2-a]indoles and Cyclopent[b]indole
  作者：Yasuyoshi Miki、Hiroko Hachiken、Atsuko Kawazoe、Yasuhiko Tsuzaki、Norihide Yanase

  DOI：10.3987/com-01-9230

  日期：——

  Treatment of 1-benzenesulfonylindole-2,3-dicarboxylic anhydride with methylenetriphenylphosphorane gave the corresponding ylide. After esterification of the carboxyl group and removal of the benzenesulfonyl group of the ylide, the obtained ylide was reacted with aldehydes to yield alpha,beta -unsaturated ketones, which were converted to pyrrolo[1,2-a]indoles. We also examined the reactivity of the anhydride with (carbethoxymethylene)triphenylphosphorane and (carbethoxyethylidene)triphenylphosphorane.