(Z)-2-diethoxyphosphoryl-3-(furan-2-yl)-3-hydroxyprop-2-enenitrile

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (Z)-2-diethoxyphosphoryl-3-(furan-2-yl)-3-hydroxyprop-2-enenitrile
• 化学式: C₁₁H₁₄NO₅P
• 分子量: 271.21
• InChiKey: ZHRARJUJUHVDGW-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  呋喃甲酰氯 、 氰甲基磷酸二乙酯 在 氢氧化钾 作用下， 以 乙腈 为溶剂， 以68%的产率得到(Z)-2-diethoxyphosphoryl-3-(furan-2-yl)-3-hydroxyprop-2-enenitrile
  参考文献：
  名称：

  摘要：

  Under conditions of the phase transfer catalysis, acylation of (thio)phosphorylacetonitriles by (het)aroyl chlorides affords the Z-enol forms of C-acylation products in high yields. Their configurations were studied by IR spectroscopy, dipole moment measurements, and ab initio quantum-chemical calculations [B3LYP/6-31G(d)]. The C=C double bond and the phosphoryl or thiophosphoryl group have an s-cis arrangement. The possibility of strong intramolecular hydrogen bonding in these conformers is the governing factor responsible for the three-dimensional structures of the compounds under investigation. Derivatives of nicotinic acid existing in the individual form as zwitterions are the only exceptions.

  DOI：

  10.1023/a:1023906822755

文献信息

• ——
  作者：I. L. Odinets

  DOI：10.1023/a:1023906822755

  日期：——

  Under conditions of the phase transfer catalysis, acylation of (thio)phosphorylacetonitriles by (het)aroyl chlorides affords the Z-enol forms of C-acylation products in high yields. Their configurations were studied by IR spectroscopy, dipole moment measurements, and ab initio quantum-chemical calculations [B3LYP/6-31G(d)]. The C=C double bond and the phosphoryl or thiophosphoryl group have an s-cis arrangement. The possibility of strong intramolecular hydrogen bonding in these conformers is the governing factor responsible for the three-dimensional structures of the compounds under investigation. Derivatives of nicotinic acid existing in the individual form as zwitterions are the only exceptions.