4,5-dichloro-3-hydroxy-6-((3-phenylallyl)oxy)phthalonitrile | 33904-12-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4,5-dichloro-3-hydroxy-6-((3-phenylallyl)oxy)phthalonitrile
• CAS: 33904-12-0
• 化学式: C₁₇H₁₀Cl₂N₂O₂
• 分子量: 345.185
• InChiKey: UWOYZDPVQLZHQD-UHFFFAOYSA-N

物化性质

• 沸点：
  545.8±50.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  77.04
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  烯丙苯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 以 二氯甲烷 、 水 为溶剂， 生成 4,5-dichloro-3-hydroxy-6-((3-phenylallyl)oxy)phthalonitrile 、 4,5-dichloro-3,6-bis((3-phenylallyl)oxy)phthalonitrile 、 肉桂醛
  参考文献：
  名称：

  通过用2,3-二氰基-5,6-二氯苯并醌（DDQ）氧化芳基丙烯来合成肉桂醛，肉桂酸酯和肉桂醛酰基

  摘要：

  1-芳基丙烯和3-芳基丙烯在水存在下与2,3-二氯-5,6-二氰基苯并醌（DDQ）氧化时生成肉桂醛（产率约80％）。芳香环上的给电子基团促进了向醛的转化。在甲醇存在下进行DDQ氧化时，肉桂酸的甲酯是主要产物。1-或3-（3,4-二甲氧基苯基）-1-丙烯在乙酸存在下的DDQ氧化可得到酰基[（E）-3-（3,4-二甲氧基苯基）-2-丙烯- 1,1-二醇]。

  DOI：

  10.1016/s0040-4039(98)00213-5

文献信息

• Synthesis of Cinnamaldehydes by Oxidation of Arylpropenes with 2,3-Dichloro-5,6-Dicyanoquinone.
  作者：Tommy Iliefski、Shiming Li、Knut Lundquist、Maria Ugalde、Pascual Román、Luis Lezama、Teófilo Rojo

  DOI：10.3891/acta.chem.scand.52-1177

  日期：——

  Alkoxylated 1-aryl-1-propenes [l-(4-methoxyphenyl)-1-propene, 1-(3,4-dimethoxyphenyl)-1 -propene, 1-(3,4,5-trimethoxyphenyl)-1-propene] and 3-aryl-1-propenes [3-(4-methoxyphenyl)-1-propene, 3-(3,4-dimethoxyphenyl)-1-propene, 3-(3,4,5-trimethoxyphenyl)-1-propene] gave cinnamaldehydes in 71-84% yield on treatment with 2,3-dichloro-5,6-dicyanoquinone (DDQ) (slight excess) at room temperature for 0.5-2 h in the two-phase system dichloromethane-water (4.1). Arylpropenes lacking electron-donating alkoxy groups (1-phenyl-1-propene, 3-phenyl-1-propene) or carrying an acetoxy group [l-(4-acetoxy-3-methoxyphenyl)-1-propene, 3-(4-acetoxy-3-methoxyphenyl)-1 -propene] were converted into cinnamaldehydes in low to moderate yields on oxidation with a large excess of DDQ in combination with long reaction times (>12 h). All the 1-aryl-1-propenes examined were rapidly converted into a mixture of mono- and bis-(3-aryl-2-propenyl) ethers of 2,3-dichloro-5,6-dicyanohydroquinone (DDHQ) on DDQ oxidation. The rate of formation of DDHQ ethers from alkoxy-substituted 3-aryl-1-propenes was slightly lower. 3-Phenyl-1-propene and also 3-(4-acetoxy-3 -methoxyphenyl)-1-propene were largely unchanged at the initial stage of the oxidation. Significant differences in the compositions of the DDHQ ether mixtures obtained from 1-aryl-1-propenes and 3-aryl-1-propenes were not observed.