5-(dimethylamino)-4-propionylthiophene-2,3-dicarbonitrile | 1547221-63-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(dimethylamino)-4-propionylthiophene-2,3-dicarbonitrile
• 英文别名: 5-(Dimethylamino)-4-propanoylthiophene-2,3-dicarbonitrile
• CAS: 1547221-63-5
• 化学式: C₁₁H₁₁N₃OS
• 分子量: 233.294
• InChiKey: OFYDTTHMPKBKME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  96.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3-二氯-5,6-二氰基-1,4-苯醌 、 3-Oxo-pentanethioic acid dimethylamide 以 乙酸乙酯 为溶剂， 以68%的产率得到5-(dimethylamino)-4-propionylthiophene-2,3-dicarbonitrile
  参考文献：
  名称：

  DDQ-Mediated Oxidative Coupling: An Approach to 2,3-Dicyanofuran (Thiophene)

  摘要：

  A facile oxidative coupling of alpha-carbonyl radicals to 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) for the synthesis of 2,3-dicyanofurans and thiophenes starting from readily available beta-diketones, simple ketones, and beta-keto thioamides in up to 95% yield in one step was developed. Mechanistic investigations revealed that a radical process could be involved in this transformation, and a water promoted C-C bond cleavage pathway is proposed for the formation of 2,3-dicyanofurans and thiophenes.

  DOI：

  10.1021/jo4026034