4-(Anthracene-9-carbonyl)-2-[1-(4-bromo-phenyl)-1-hydroxy-meth-(E)-ylidene]-5-methylamino-thiophen-3-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4-(Anthracene-9-carbonyl)-2-[1-(4-bromo-phenyl)-1-hydroxy-meth-(E)-ylidene]-5-methylamino-thiophen-3-one
• 英文别名: (2E)-4-(anthracene-9-carbonyl)-2-[(4-bromophenyl)-hydroxymethylidene]-5-(methylamino)thiophen-3-one
• 化学式: C₂₇H₁₈BrNO₃S
• 分子量: 516.415
• InChiKey: HBHSALDSAXRSML-WNAAXNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (Z)-2-(Anthracene-9-carbonyl)-3-[2-(4-bromo-phenyl)-2-oxo-ethylsulfanyl]-3-methylamino-acrylic acid methyl ester 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 4-(Anthracene-9-carbonyl)-2-[1-(4-bromo-phenyl)-1-hydroxy-meth-(E)-ylidene]-5-methylamino-thiophen-3-one
  参考文献：
  名称：

  Reaktionsverhalten von ?-Oxo-carbons�urederivaten der Anthracenreihe bei der Synthese von Thiophenen

  摘要：

  beta-Oxo-1-anthracenepropionate (3) reacts step by step with phenylisothiocyanate and alpha-CH-acidic halo compounds to keten-S,N-acetals 4, followed by cyclocondensation to give the 4-(1-anthracenyl)-thiophene-3-carboxylates 5. In contrast, the reaction of beta-oxo-9-anthracenepropionate (6) with isothiocyanates and alpha-CH-acidic halo compounds yields 5-acyl-2-amino-3-(9-anthracenoyl)-4-hydroxy-thiophenes 8. This is caused by the sterical hindrance of the keto group of the anthracene in position 9; thus, the cyclocondensation proceeds via reaction of the ester group of the beta-oxo-propionate. In the same way, 9-acetylanthracene reacts with phenylisothiocyanate and alpha-CH-acidic compounds to keten-S,N-acetals 10 and, in an additional step, to 2-anilino-3-(9-anthracenoyl)-thiophenes 11 and 2-(9-anthracenoyl)-methylene-3,4-diphenyl-2,3-dihydro-(1,3)-thiazole 12, respectively. The structure of all new compounds was determinated by 2D NOESY NMR spectroscopy.

  DOI：

  10.1007/bf00844693

表征谱图