△6-去氢弥罗松酚 | 34539-84-9

• 物质功能分类: 香精与香料 - 酚类 - 合成香料 - 酚类、醚类和环氧化物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: △6-去氢弥罗松酚
• 中文别名: 6-去氢弥罗松酚
• 英文名称: Δ⁹-dehydro-ferruginol
• 英文别名: (-)-abieta-6,8,11,13-tetrene-12-ol；Δ⁹-ferruginol；6,7-dehydroferruginol；6,7-dehydroferrginol；6,7-dehydroferrugiol；dehydroferruginol；(4bS,8aS)-4b,8,8-trimethyl-2-propan-2-yl-5,6,7,8a-tetrahydrophenanthren-3-ol
• CAS: 34539-84-9
• 化学式: C₂₀H₂₈O
• 分子量: 284.442
• InChiKey: NCHINJPZLGMLCY-AZUAARDMSA-N

物化性质

• 沸点：
  392.0±42.0 °C(Predicted)
• 密度：
  1.004±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  △6-去氢弥罗松酚 在 吡啶 、 lithium aluminium tetrahydride 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 31.75h， 生成 6β-hydroxyferruginol
  参考文献：
  名称：

  Haslinger, Ernst; Michl, Guenter, Liebigs Annalen der Chemie, 1989, p. 677 - 686

  摘要：

  DOI：
• 作为产物：
  描述：

  6β-hydroxyferruginol 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以4 mg的产率得到△6-去氢弥罗松酚
  参考文献：
  名称：

  6-Oxoferruginol and 6α-Acetoxyferruginol, New Abietane-Type Diterpenes from the Heartwood of Juniperus formosana

  摘要：

  New abietane diterpenes, 6 alpha-acetoxyferruginol and 6-oxoferruginol were isolated from the heartwood of Juniperus formosana Hay. var. concolor Hay. together with the known compounds ferruginol, sugiol, xanthoperol, 5-epi-xanthoperol, and 6,12-'dihydroxyabieta-5,8,11,13-tetraen-7-one. The structures of the new compounds were elucidated on the basis of spectral and chemical evidence.

  DOI：

  10.1021/np960389x

文献信息

• Stereoselective Partial Synthesis of (+)-Pisiferic Acid
  作者：J�rgen Geiwiz、Ernst Haslinger

  DOI：10.1002/hlca.19950780404

  日期：1995.6.28

  (+)-Pisiferic acid (1), an antibiotic active against Gram-negative and Gram-positive bacteria, was synthesized starting from dehydroabietic acid (2) or abietic acid (26). The terpene ring system was functionalized and a Barton reaction used to oxidize Me(20). The intermediates of this photochemical reaction were isolated and characterized.

  从脱氢松香酸（2）或松香酸（26）开始合成了（+）-吡啶甲酸（1），它对革兰氏阴性和革兰氏阳性细菌具有活性。萜环系统功能化和Barton反应用于氧化Me（20）。分离并表征了该光化学反应的中间体。
• Unprecedented Elimination Reactions of Cyclic Aldols: A New Biosynthetic Pathway toward the Taiwaniaquinoid Skeleton
  作者：Juan J. Guardia、Antonio Fernández、José Justicia、Houda Zentar、Ramón Alvarez-Manzaneda、Enrique Alvarez-Manzaneda、Rachid Chahboun

  DOI：10.3390/molecules28041524

  日期：——

  The acid treatment of 6,7-seco-abietane dialdehydes gives, in high yield, the corresponding derivatives with the 4a-methyltetrahydrofluorene skeleton of taiwaniaquinoids. A mechanism involving the elimination of formic acid from the cyclic aldol intermediate is proposed here. This process can be postulated as a new biogenetic pathway from abietane diterpenes to taiwaniaquinoids. Using this novel reaction

  6,7-seco-abietane 二醛的酸处理以高收率得到具有 taiwaniaquinoids 的 4a-甲基四氢芴骨架的相应衍生物。这里提出了一种涉及从环状羟醛中间体中消除甲酸的机制。这个过程可以假设为从松香二萜到台湾醌的新的生物遗传途径。利用这一新反应，首次获得了具有生物活性的天然铜酚和紫杉醇的对映体特异性合成。
• Bredenberg, Acta Chemica Scandinavica (1947), 1957, vol. 11, p. 927,930
  作者：Bredenberg

  DOI：——

  日期：——
• Antioxidant activity and mechanism of the abietane-type diterpene ferruginol
  作者：H. Saijo、H. Kofujita、K. Takahashi、T. Ashitani

  DOI：10.1080/14786419.2014.997233

  日期：2015.9.17

  The antioxidant activity of the abietane-type diterpene ferruginol was evaluated by comparison with that of carnosic acid, (+/-)--tocopherol and dibutylhydroxytoluene using 2,2-diphenyl-1-picrylhydrazyl, -carotene bleaching and linoleic acid assays. Ferruginol had the lowest antioxidant activity of this group using the 2,2-diphenyl-1-picrylhydrazyl and -carotene methods in polar solvent buffer. However, ferruginol exhibited stronger activity than carnosic acid and -tocopherol for linoleic acid oxidation under non-solvent conditions. Five peaks corresponding to ferruginol derivatives were detected through GC-MS analysis of the reaction between ferruginol and methyl linoleate. The three reaction products were identified as dehydroferruginol, 7-hydroxyferruginol and sugiol, and the other two peaks were assumed to be 7-hydroxyferruginol and the quinone methide derivative of ferruginol. The time course of the reaction suggests that the quinone methide was produced early in the reaction and reacted further to produce dehydroferruginol, 7-hydroxyferruginol and sugiol. Thus, we inferred that quinone methide formation was a key step in the antioxidant reaction of ferruginol.
• HASLINGER, ERNST;MICHL, GUNTER, LIEBIGS ANN. CHEM.,(1989) N, C. 677-686
  作者：HASLINGER, ERNST、MICHL, GUNTER

  DOI：——

  日期：——