4-(6-(4-(dimethylamino)phenyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,6-hexahydrofuro[2,3-d]pyrimidin-5-yl)benzonitrile | 1259377-27-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(6-(4-(dimethylamino)phenyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,6-hexahydrofuro[2,3-d]pyrimidin-5-yl)benzonitrile
• CAS: 1259377-27-9
• 化学式: C₂₃H₂₂N₄O₃
• 分子量: 402.453
• InChiKey: NFTBEPNVLBFJOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  80.26
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  (4-cyanobenzyl)dimethylsulfonium tetrafluoroborate 、 5-[[4-(二甲基氨基)苯基]亚甲基]-1,3-二甲基巴比妥酸 在 potassium carbonate 作用下， 以 氯仿 、 水 为溶剂， 反应 2.0h， 以56%的产率得到4-(6-(4-(dimethylamino)phenyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,6-hexahydrofuro[2,3-d]pyrimidin-5-yl)benzonitrile
  参考文献：
  名称：

  Scope and Limitations of Cyclopropanations with Sulfur Ylides

  摘要：

  The rates of the reactions of the stabilized and semistabilized sulfur ylides 1a-g with benzhydrylium ions (2a-e) and Michael acceptors (2f-v) have been determined by UV-vis spectroscopy in DMSO at 20 degrees C. The second-order rate constants (log k(2)) of these reactions correlate linearly with the electrophilicity parameters E of the electrophiles 2 as required by the correlation log k(2) = s(N + E), which allowed us to calculate the nucleophile-specific parameters N and s for the sulfur ylides 1a-g. The rate constants for the cyclopropanation reactions of sulfur ylides with Michael acceptors lie on the same correlation line as the rate constants for the reactions of sulfur ylides with carbocations. This observation is in line with a stepwise mechanism for the cyclopropanation reactions in which the first step, nucleophilic attack of the sulfur ylides at the Michael acceptors, is rate determining. As the few known pK(aH) values for sulfur ylides correlate poorly with their nucleophilic reactivities, the data reported in this work provide the first quantitative approach to sulfur ylide reactivity.

  DOI：

  10.1021/ja1084749