3-(3,5-dimethoxy-4-trimethylsilyloxyphenyl)-2-propenoic acid methyl ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(3,5-dimethoxy-4-trimethylsilyloxyphenyl)-2-propenoic acid methyl ester
• 英文别名: Cinnamic acid, 3,5-dimethoxy-4-(trimethylsiloxy)-, methyl ester；methyl (E)-3-(3,5-dimethoxy-4-trimethylsilyloxyphenyl)prop-2-enoate
• 化学式: C₁₅H₂₂O₅Si
• 分子量: 310.422
• InChiKey: WKCLSJHIGCBGDX-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N,O-双三甲硅基乙酰胺 、 methyl (E)-sinapate 以 四氯化碳 为溶剂， 生成 3-(3,5-dimethoxy-4-trimethylsilyloxyphenyl)-2-propenoic acid methyl ester
  参考文献：
  名称：

  Fragmentation of trimethylsilyl derivatives of 2-alkoxyphenols: A further violation of the ‘even-electron rule’

  摘要：

  AbstractThe mass spectra of trimethylsilyl (TMS) ethers of 2‐methoxyphenols show abundant [M–30]+˙ ions originating from consecutive loss of two methyl radicals. This is illustrated by comparison of the accurate mass‐measured and linked‐scan spectra of the TMS derivatives of 2‐methoxyphenol (guaiacol), 4‐hydroxy‐3‐methoxybenzaldehyde (vanillin) and 3‐(4‐hydroxy‐3‐methoxyphenyl)‐2‐propenoic acid methyl ester (ferulic acid methyl ester) with those of the TMS derivatives of phenol, 4‐hydroxybenzaldehyde, 3‐(4‐hydroxyphenyl)‐2‐propenoic acid methyl ester (p‐coumaric acid methyl ester), 3‐methoxyphenol and 4‐methoxyphenol. This distinctive ortho effect is valuable in the identification of isomeric phenolic compounds. In the spectra of the TMS derivatives of 2‐ethoxyphenol and 2‐propoxyphenol the sequential loss of two radicals is less pronounced, because elimination of the side‐chain and a methyl group with rearrangement and hydrogen migration is competitive.

  DOI：

  10.1002/oms.1210201005

文献信息

• Fragmentation of trimethylsilyl derivatives of 2-alkoxyphenols: A further violation of the ‘even-electron rule’
  作者：Dietlinde Krauss、Hans Georg Mainx、Bernhard Tauscher、Peter Bischof

  DOI：10.1002/oms.1210201005

  日期：1985.10

  AbstractThe mass spectra of trimethylsilyl (TMS) ethers of 2‐methoxyphenols show abundant [M–30]+˙ ions originating from consecutive loss of two methyl radicals. This is illustrated by comparison of the accurate mass‐measured and linked‐scan spectra of the TMS derivatives of 2‐methoxyphenol (guaiacol), 4‐hydroxy‐3‐methoxybenzaldehyde (vanillin) and 3‐(4‐hydroxy‐3‐methoxyphenyl)‐2‐propenoic acid methyl ester (ferulic acid methyl ester) with those of the TMS derivatives of phenol, 4‐hydroxybenzaldehyde, 3‐(4‐hydroxyphenyl)‐2‐propenoic acid methyl ester (p‐coumaric acid methyl ester), 3‐methoxyphenol and 4‐methoxyphenol. This distinctive ortho effect is valuable in the identification of isomeric phenolic compounds. In the spectra of the TMS derivatives of 2‐ethoxyphenol and 2‐propoxyphenol the sequential loss of two radicals is less pronounced, because elimination of the side‐chain and a methyl group with rearrangement and hydrogen migration is competitive.