Methyl 2-[4-cyano-5-(furan-2-yl)furan-2-yl]acetate | 1307291-58-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: Methyl 2-[4-cyano-5-(furan-2-yl)furan-2-yl]acetate
• 英文别名: methyl 2-[4-cyano-5-(furan-2-yl)furan-2-yl]acetate
• CAS: 1307291-58-2
• 化学式: C₁₂H₉NO₄
• 分子量: 231.208
• InChiKey: GFSSMSUHYCRBFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-呋喃甲酰乙腈 、 3-(methoxycarbonyl)propargyl bromide 在 三苯基膦 、 silver(l) oxide 作用下， 以 二甲基亚砜 为溶剂， 反应 1.33h， 以87%的产率得到Methyl 2-[4-cyano-5-(furan-2-yl)furan-2-yl]acetate
  参考文献：
  名称：

  Phosphine-Catalyzed [3 + 2] Annulations of γ-Functionalized Butynoates and 1C,3O-Bisnucleophiles: Highly Selective Reagent-Controlled Pathways to Polysubstituted Furans

  摘要：

  In this paper, a reagent-controlled [3 + 2] annulation of gamma-functionalized butynoates 1 and 1C,3O-bisnucleophiles 2 is reported, which leads to three distinct furan skeletons 3-5. A PPh3 catalyst preferentially attached the beta-position of 1a, facilitating a-addition to furnish Type I annulations. With the assistance of Ag2O, Type II annulations were achieved via selective gamma-substitution. In the absence of the PPh3 catalyst, the reagent Cs2CO3 promoted beta-addition to realize Type III annulations.

  DOI：

  10.1021/ol200940a

文献信息

• Phosphine-Catalyzed [3 + 2] Annulations of γ-Functionalized Butynoates and 1<i>C</i>,3<i>O</i>-Bisnucleophiles: Highly Selective Reagent-Controlled Pathways to Polysubstituted Furans
  作者：Jian Hu、Yabing Wei、Xiaofeng Tong

  DOI：10.1021/ol200940a

  日期：2011.6.17

  In this paper, a reagent-controlled [3 + 2] annulation of gamma-functionalized butynoates 1 and 1C,3O-bisnucleophiles 2 is reported, which leads to three distinct furan skeletons 3-5. A PPh3 catalyst preferentially attached the beta-position of 1a, facilitating a-addition to furnish Type I annulations. With the assistance of Ag2O, Type II annulations were achieved via selective gamma-substitution. In the absence of the PPh3 catalyst, the reagent Cs2CO3 promoted beta-addition to realize Type III annulations.