3,4-二甲氧基-6-硝基肉桂酸 | 880074-30-6

• 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
• 中文名称: 3,4-二甲氧基-6-硝基肉桂酸
• 英文名称: 3,4-dimethoxy-6-nitrocinnamic acid
• 英文别名: 3,4-dimethoxy-2-nitro-cinnamic acid；3,4-Dimethoxy-2-nitro-zimtsaeure；(E)-3-(3,4-dimethoxy-2-nitrophenyl)prop-2-enoic acid
• CAS: 880074-30-6
• 化学式: C₁₁H₁₁NO₆
• 分子量: 253.211
• InChiKey: DRILANDLIDDRPI-GQCTYLIASA-N

物化性质

• 熔点：
  229 °C
• 沸点：
  473.2±45.0 °C(Predicted)
• 密度：
  1.369±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4-二甲氧基-6-硝基肉桂酸 在 三溴化硼 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 (2E)-3-(4,5-二羟基-2-硝基苯基)丙烯酸
  参考文献：
  名称：

  Synthesis and physico-chemical properties of nitrocaffeic acids

  摘要：

  The synthesis and spectroscopic properties of the three isomers of nitrocaffeic acid are described. The three pK(a) s of each isomer were measured by UV-visible spectroscopy. The comparison of the UV-visible spectra of nitrocaffeic acids and those obtained from the reaction of caffeic acid with reactive nitrogen species led to the conclusion that the nitration of caffeic acid with acidic nitrite does not significantly occur and confirmed the absence of nitration when caffeic acid reacts with peroxynitrite. Attempts to obtain free radical species from nitrocaffeic acids by classical methods showed a different reactivity to that of nitroaromatics and catechols. Nitrocaffeic acids do not autoxidize under aqueous basic conditions and are insensitive to t-BuOK or O-2(-.) (two reactants known for their capabilities to oxidize catechols and reduce nitroaromatics). Nitroaromatic anion radicals may be obtained using sodium borohydride as reductant and are particularly stable under an uncontrolled atmosphere. Copyright (C) 2000 John Wiley & Sons, Ltd.

  DOI：

  10.1002/1099-1395(200009)13:9<511::aid-poc283>3.0.co;2-8
• 作为产物：
  描述：

  3,4-二甲氧基-2-硝基苯甲醛 、 乙酸酐 在 sodium salt of the 6-methoxy-3-ethyl-phenylacetic acid 作用下， 生成 3,4-二甲氧基-6-硝基肉桂酸
  参考文献：
  名称：

  Gulland; Virden, Journal of the Chemical Society, 1928, p. 931

  摘要：

  DOI：

文献信息

• Gulland; Virden, Journal of the Chemical Society, 1928, p. 1482
  作者：Gulland、Virden

  DOI：——

  日期：——
• Gulland; Virden, Journal of the Chemical Society, 1928, p. 931
  作者：Gulland、Virden

  DOI：——

  日期：——
• Synthesis and physico-chemical properties of nitrocaffeic acids
  作者：J. L. Grenier、N. Cotelle、J. P. Catteau、P. Cotelle

  DOI：10.1002/1099-1395(200009)13:9<511::aid-poc283>3.0.co;2-8

  日期：2000.9

  The synthesis and spectroscopic properties of the three isomers of nitrocaffeic acid are described. The three pK(a) s of each isomer were measured by UV-visible spectroscopy. The comparison of the UV-visible spectra of nitrocaffeic acids and those obtained from the reaction of caffeic acid with reactive nitrogen species led to the conclusion that the nitration of caffeic acid with acidic nitrite does not significantly occur and confirmed the absence of nitration when caffeic acid reacts with peroxynitrite. Attempts to obtain free radical species from nitrocaffeic acids by classical methods showed a different reactivity to that of nitroaromatics and catechols. Nitrocaffeic acids do not autoxidize under aqueous basic conditions and are insensitive to t-BuOK or O-2(-.) (two reactants known for their capabilities to oxidize catechols and reduce nitroaromatics). Nitroaromatic anion radicals may be obtained using sodium borohydride as reductant and are particularly stable under an uncontrolled atmosphere. Copyright (C) 2000 John Wiley & Sons, Ltd.