5-Methoxy-furan-2-carbonitrile

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Methoxy-furan-2-carbonitrile
• 英文别名: 5-Methoxyfuran-2-carbonitrile；5-methoxyfuran-2-carbonitrile
• 化学式: C₆H₅NO₂
• 分子量: 123.111
• InChiKey: DZSPGFZTDCNMII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  [(Z)-(5-methoxyfuran-2-yl)methylideneamino] benzoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 生成 苯甲酸阴离子 、 5-Methoxy-furan-2-carbonitrile
  参考文献：
  名称：

  Elimination Reactions of (Z)-Thiophene- and (Z)-Furan-2-carbaldehyde O-Benzoyloximes. Effect of β-Aryl Group upon the Nitrile-Forming Anti Transition State

  摘要：

  Elimination reactions of(Z)-thiophene- and (Z)-furan-2-carbaldehyde O-benzoyloximes 1 and 2 with DBU in MeCN have been investigated kinetically. The reactions are second order and exhibit substantial values of Hammett rho and k(H)/k(D) values, and an E2 mechanism is evident. The relative rates of elimination from (Z)-ArCH=NOC(O)C6H4Y are 1/1.1/0.6 for Ar = phenyl/thienyl/furyl, respectively. For reactions of 1 with DBU in MeCN, k(H)/k(D) = 8.2 +/- 0.1, Hammett rho = 1.22 +/- 0.19, beta(1g) = -0.43 +/- 0.01, Delta H-double dagger = 5.9 +/- 0.1 kcal/mol, and Delta S-double dagger = -28.5 +/- 0.3 eu have been determined. The corresponding values for 2 are k(H)/k(D) = 8.8 +/- 0.2, rho = 1.87 +/- 0.05, beta(1g) = -0.55 +/- 0.10, Delta H-double dagger = 6.5 +/- 0.1 kcal/mol, and Delta S-double dagger = -29.0 +/- 1.5 eu. The k(H)/k(D), Hammett rho, and \beta(1g)\ values increase as the beta-aryl group is changed in the order phenyl < thienyl < furyl. The results indicate that the transition state structure for the nitrile-forming elimination changes slightly toward product-like with the change of the beta-aryl group.

  DOI：

  10.1021/jo981169m