2-丙烯醛,3-[(2R,3S)-3-戊基噁丙环基]-,(2E)-rel- | 154002-67-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-丙烯醛,3-[(2R,3S)-3-戊基噁丙环基]-,(2E)-rel-
• 英文名称: cis-4,5-epoxy-(E)-2-decenal
• 英文别名: (E)-3-[(2R,3S)-3-pentyloxiran-2-yl]prop-2-enal
• CAS: 154002-67-2
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: HIOMEXREAUSUBP-IUUOVRRDSA-N

物化性质

• 沸点：
  273.3±15.0 °C(Predicted)
• 密度：
  1.022±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  [(2S,3S)-3-pentyloxiran-2-yl]methanol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 10.0h， 生成 2-丙烯醛,3-[(2R,3S)-3-戊基噁丙环基]-,(2E)-rel-
  参考文献：
  名称：

  Characterization of Epoxydecenal Isomers as Potent Odorants in Black Tea (Dimbula) Infusion

  摘要：

  In a black tea (Dimbula) infusion, the potent "sweet and/or juicy" odorants were identified as the cis- and trans-4,5-epoxy-(E)-2-decenals by comparison of their gas chromatography retention indices, mass spectra, and odor quality to those of the actual synthetic compounds. Of the two odorants, cis-4,5-epoxy-(E)-2-decenal has been identified for the first time in the black tea. On the basis of the aroma extract dilution analysis on the flavor distillate obtained using the solvent-assisted flavor evaporation technique from the black tea infusion, these isomers showed higher flavor dilution (FD) factors. The FD factors and concentrations of these odorants in the black tea infusion were observed to be much higher than those from Japanese green tea. In addition, the model studies showed that these odorants were generated from linoleic acid and its hydroperoxides by heating, but the generated amounts of these odorants from linoleic acid were much less than those of its hydroperoxides. It can be assumed from these results that the withering and fermentation, which are characteristic processes during the manufacturing of the black tea, which includes the enzymatic reaction such as lipoxygenase, is one of the most important factors for the formation of the epoxydecenal isomers.

  DOI：

  10.1021/jf0603127

文献信息

• Studies on the Aroma of Five Fresh Tomato Cultivars and the Precursors of <i>cis</i>- and <i>trans</i>-4,5-Epoxy-(<i>E</i>)-2-Decenals and Methional
  作者：Florian Mayer、Gary R. Takeoka、Ron G. Buttery、Linda C. Whitehand、Michael Naim、Haim D. Rabinowitch

  DOI：10.1021/jf0732915

  日期：2008.5.1

  2-phenylethanol, or 2-isobutylthiazole had higher odor units in the less preferred cultivars. Simulation of the odor of the selected tomato cultivars by preparation of aroma models and comparison with the corresponding real samples confirmed that all important fresh tomato odorants were identified, that their concentrations were determined correctly in all five cultivars, and that differences in concentration

  使用香气提取物筛选了三个鲜味（BR-139，FA-624和FA-612）和两个鲜味（R-144和R-175）的鲜温室番茄品种，它们的风味特征明显不同，它们的风味特征明显不同稀释分析（AEDA）。根据AEDA结果，使用气相色谱-质谱法（GC-MS）在这5个品种中选择了19种挥发物进行定量。化合物，例如1-戊烯-3-一，（E，E）-和（E，Z）-2,4-癸二烯醛和4-羟基-2,5-二甲基-3（2 H）-呋喃酮）在更优选的品种中具有较高的气味单位，而甲基，苯乙醛，2-苯基乙醇或2-异丁基噻唑在较不优选的品种中具有较高的气味单位。通过制备香气模型并与相应的实际样品进行比较来模拟所选番茄品种的气味，证实了所有重要的新鲜番茄香味剂均已识别，在所有五个品种中均已正确确定了它们的浓度，并且浓度差异（尤其是浓度）有所差异。上述化合物可以区分它们，并引起差异偏爱。为帮助阐明关键气味的形成途径，将标记的前体添加到番茄中。证实了亚油酸的顺式和反式4
• Regio- and enantioselective catalytic epoxidation of conjugated polyenes. Formal synthesis of LTA4 methyl ester
  作者：Sukbok Chang、Nam Ho Lee、Eric N. Jacobsen

  DOI：10.1021/jo00077a001

  日期：1993.12

  The (salen)Mn(III)-catalyzed asymmetric epoxidation reaction exhibits regioselectivity for attack at cis double bonds of conjugated dienes to afford enantiomerically enriched trans-vinyl epoxides as the major products.