officinalin isobutyrate | 61467-56-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: officinalin isobutyrate
• 英文别名: 6-Carbomethoxy-7-isobutyroxy-cumarin；methyl 7-(2-methylpropanoyloxy)-2-oxochromene-6-carboxylate
• CAS: 61467-56-9
• 化学式: C₁₅H₁₄O₆
• 分子量: 290.273
• InChiKey: VUVWVGLISBHUCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  officinalin isobutyrate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以94%的产率得到peuruthenicin
  参考文献：
  名称：

  Study of plant coumarins 1. Transformations of peucedanin

  摘要：

  建立了前胡素或奥雷西隆与分子溴的溴化反应制备的2-溴奥雷西隆的结构。研究了该溴化物与吡啶、三乙胺和吗啉等胺以及与乙酸钠和氢氧化钾的反应产物的组成和结构。前胡素与间氯过苯甲酸反应得到前胡素异丁酸酯。

  DOI：

  10.1007/s11172-006-0263-6
• 作为产物：
  描述：

  3-甲氧基-2-丙-2-基呋喃并[3,2-g]苯并吡喃-7-酮 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 16.0h， 以57%的产率得到officinalin isobutyrate
  参考文献：
  名称：

  Study of plant coumarins 1. Transformations of peucedanin

  摘要：

  建立了前胡素或奥雷西隆与分子溴的溴化反应制备的2-溴奥雷西隆的结构。研究了该溴化物与吡啶、三乙胺和吗啉等胺以及与乙酸钠和氢氧化钾的反应产物的组成和结构。前胡素与间氯过苯甲酸反应得到前胡素异丁酸酯。

  DOI：

  10.1007/s11172-006-0263-6

文献信息

• Secondary metabolites of Peucedanum tauricum fruits
  作者：Hailemichael Tesso、Wilfried A. König、Karl-Heinz Kubeczka、Magdalena Bartnik、Kazimierz Glowniak

  DOI：10.1016/j.phytochem.2005.01.022

  日期：2005.3

  From the essential oil of fruits of Peucedanum tauricum Bieb., two guaiane type sesquiterpene hydrocarbons guaia-1(10),11-diene (1) and guaia-9,11-diene (2) were identified. The structures of 1 and 2 were assigned by 1D and 2D NMR analysis. The relative configurations of the compounds were established by 2D-NOESY experiments while the absolute configurations were deduced through chemical correlations with (+)-gamma-gurjunene (9) and capillary GC analysis using modified cyclodextrins as the stationary phases. From the dichloromethane extract of the less volatile fraction of the fruits, coumarins, viz. peucedanin (3), oxypeucedanin hydrate (4) and officinalin isobutyrate (5) were isolated. Compound 5 was confirmed to be 6-carbomethoxy-7-isobutyroxycoumarin by its ID and 2D NMR data as well as by conversion into officinalin (7) by alkaline hydrolysis. Peuruthenicin, a positional isomer of officinalin, is assigned structure 8 on spectral basis. Bergapten (6) was identified by its mass spectrum. This is the first report on the isolation of compounds 4 and 5 from P. tauricum. (c) 2005 Elsevier Ltd. All rights reserved.