5-methylfuran-2,3,4-tricarbonitrile | 1476782-12-3

• 分子结构分类: 有机化合物
• 英文名称: 5-methylfuran-2,3,4-tricarbonitrile
• CAS: 1476782-12-3
• 化学式: C₈H₃N₃O
• 分子量: 157.131
• InChiKey: JSFPFMAHMZCOAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  氰基丙酮 、 2,3-二氯-5,6-二氰基-1,4-苯醌 以 乙酸乙酯 为溶剂， 以77%的产率得到5-methylfuran-2,3,4-tricarbonitrile
  参考文献：
  名称：

  An Efficient Access to Fluorescent 2,3,4-Tricyanofurans from α-Cyano Ketones Using DDQ as Maleonitrile Building Block

  摘要：

  An efficient synthetic method was developed for the synthesis of 2,3,4-tricyanofurans from -cyano ketones using DDQ as maleonitrile building block under very mild conditions. This methodology allows for the construction of a new kind of fluorescent core framework.

  DOI：

  10.1055/s-0033-1339501

文献信息

• DDQ-Mediated Oxidative Coupling: An Approach to 2,3-Dicyanofuran (Thiophene)
  作者：Zheng-Lin Wang、Hong-Liang Li、Li-Shi Ge、Xing-Lan An、Zi-Gang Zhang、Xiaoyan Luo、John S. Fossey、Wei-Ping Deng

  DOI：10.1021/jo4026034

  日期：2014.2.7

  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.