3-{4-[2-(3,4-dimethoxyphenyl)-2-hydroxyethoxy]-3-methoxyphenyl}prop-2-enal

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: 3-{4-[2-(3,4-dimethoxyphenyl)-2-hydroxyethoxy]-3-methoxyphenyl}prop-2-enal
• 英文别名: β-(coniferyl aldehyde) ether of veratrylglycol；(E)-3-[4-[2-(3,4-dimethoxyphenyl)-2-hydroxyethoxy]-3-methoxyphenyl]prop-2-enal
• 化学式: C₂₀H₂₂O₆
• 分子量: 358.391
• InChiKey: PMJNHJFWBIGFDB-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  反式-3-(4-羟基-3-甲氧基苯基)-2-丙烯-1-醇 在 sodium tetrahydroborate 、 potassium carbonate 、 对苯醌 作用下， 以 1,4-二氧六环 、 二乙二醇二甲醚 、 丙酮 为溶剂， 反应 32.5h， 生成 3-{4-[2-(3,4-dimethoxyphenyl)-2-hydroxyethoxy]-3-methoxyphenyl}prop-2-enal
  参考文献：
  名称：

  Tetramethylammonium Hydroxide (TMAH) Thermochemolysis of Lignin:  Behavior of 4-O-Etherified Cinnamyl Alcohols and Aldehydes

  摘要：

  The thermochemolytic behavior of 4-O-etherified cinnamyl alcohols and aldehydes in lignin was investigated in the presence of tetramethylammonium hydroxide (TMAH) (315 degrees C/4 s), using veratrylglycol-beta-(coniferyl alcohol) ether (1a), veratrylglycol-beta-(sinapyl alcohol) ether (1b), and veratrylglycol-beta-(coniferyl aldehyde) ether (2). The methylated products were monitored with gas chromatography-mass spectrometry. Dimers 1a and 1b provided the coniferyl and sinapyl alcohol dimethyl ethers consisting of three isomers, respectively. Coniferyl alcohol dimethyl ether isomers were also observed in the TMAH thermochemolysis pyrolysates of a bulk dehydrogenation polymer of coniferyl alcohol and a Japanese cedar (Cryptomeria japonica) wood. Coniferyl aldehyde methyl ether was not provided from TMAH thermochemolyses of coniferyl aldehyde, 2, a dehydrogenation polymer of coniferyl aldehyde, and the cedar wood. The former three provided veratryl aldehyde in a large abundance, instead of coniferyl aldehyde methyl ether. Sinapyl aldehyde provided 3,4,5-trimethoxybenzaldehyde in a large abundance and sinapyl aldehyde methyl ether in a trace abundance. The results showed that TMAH thermochemolysis is an effective tool to obtain information on cinnamyl alcohol end groups, but is not applicable to analysis of cinnamyl aldehyde end groups.

  DOI：

  10.1021/jf058085g

文献信息

• Tetramethylammonium Hydroxide (TMAH) Thermochemolysis of Lignin:  Behavior of 4-<i>O</i>-Etherified Cinnamyl Alcohols and Aldehydes
  作者：Ken-ichi Kuroda、Akiko Nakagawa-izumi

  DOI：10.1021/jf058085g

  日期：2005.11.1

  The thermochemolytic behavior of 4-O-etherified cinnamyl alcohols and aldehydes in lignin was investigated in the presence of tetramethylammonium hydroxide (TMAH) (315 degrees C/4 s), using veratrylglycol-beta-(coniferyl alcohol) ether (1a), veratrylglycol-beta-(sinapyl alcohol) ether (1b), and veratrylglycol-beta-(coniferyl aldehyde) ether (2). The methylated products were monitored with gas chromatography-mass spectrometry. Dimers 1a and 1b provided the coniferyl and sinapyl alcohol dimethyl ethers consisting of three isomers, respectively. Coniferyl alcohol dimethyl ether isomers were also observed in the TMAH thermochemolysis pyrolysates of a bulk dehydrogenation polymer of coniferyl alcohol and a Japanese cedar (Cryptomeria japonica) wood. Coniferyl aldehyde methyl ether was not provided from TMAH thermochemolyses of coniferyl aldehyde, 2, a dehydrogenation polymer of coniferyl aldehyde, and the cedar wood. The former three provided veratryl aldehyde in a large abundance, instead of coniferyl aldehyde methyl ether. Sinapyl aldehyde provided 3,4,5-trimethoxybenzaldehyde in a large abundance and sinapyl aldehyde methyl ether in a trace abundance. The results showed that TMAH thermochemolysis is an effective tool to obtain information on cinnamyl alcohol end groups, but is not applicable to analysis of cinnamyl aldehyde end groups.