(4aS,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,10a-hexahydrophenanthrene | 70614-86-7

• 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
• 英文名称: (4aS,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,10a-hexahydrophenanthrene
• 英文别名: (-)-6,7-dehydroferruginyl methyl ether；6,7-dehydroferruginol methyl ether；(4aS,10aS)-6-methoxy-1,1,4a-trimethyl-7-propan-2-yl-2,3,4,10a-tetrahydrophenanthrene
• CAS: 70614-86-7
• 化学式: C₂₁H₃₀O
• 分子量: 298.469
• InChiKey: NCPDWQQTBMASKJ-PZJWPPBQSA-N

物化性质

• 沸点：
  393.9±42.0 °C(Predicted)
• 密度：
  0.966±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4aS,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,10a-hexahydrophenanthrene 在 palladium on activated charcoal 氢气 、 三溴化硼 作用下， 以 二氯甲烷 、 氯仿 、 乙酸乙酯 为溶剂， 反应 33.0h， 生成 12-benzoyloxy-11-hydroxyabieta-8,11,13-triene
  参考文献：
  名称：

  Synthesis of variously oxidized abietane diterpenes and their antibacterial activities against MRSA and VRE

  摘要：

  Variously oxidized 12 natural abietanes, 6,7-dehydroferruginol methyl ether (3), ferruginol (5), 11-hydroxy-12-oxo-7,9(11),13-abietatriene (7), royleanone (9), demethyl cryptojaponol (12), salvinolone (14), sugiol methyl ether (16), sugiol (17), 5,6-dehydrosugiol methyl ether (19), 5,6-dehydrosugiol (20), 6 beta -hydroxyferruginol (23), and taxodione (25) were synthesized. Antimicrobial activities of synthesized phenolic diterpenes and their related compounds against MRSA and VRE were evaluated. Phenols (12-hydroxyabieta-8,11,13-trien-6-one 22 and 23), catechols (12 and 14) and taxodione 25 showed potent activity with 4-10 mug/mL of MIC against MRSA and 4-16 mug/mL of MIC against VRE. (-)-Ferruginol showed more potent activity than natural type (+)-ferruginol. Quinone methide 7 showed the most potent activity with 0.5-1 mug/mL of MIC against both MRSA and VRE. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00253-4
• 作为产物：
  描述：

  (S)-α-Cyclogeraniol 在 palladium on activated charcoal chromium(VI) oxide 、 sodium tetrahydroborate 、 正丁基锂 、 三氯化铝 、 三氟化硼乙醚 、 氢气 、 sodium acetate 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 溶剂黄146 、 苯 为溶剂， 反应 12.5h， 生成 (4aS,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,10a-hexahydrophenanthrene
  参考文献：
  名称：

  Stereoselective synthesis of (−)-6,7-dehydroferruginyl methyl ether

  摘要：

  A stereoselective synthetic route to (-)-6,7-dehydroferruginyl methyl ether was developed from (S)-(-)-alpha-cyclocitral. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00007-0

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。
• New strategy toward the diverted synthesis of oxidized abietane diterpenes via oxidation of 6,7-dehydroferruginol methyl ether with dimethyldioxirane
  作者：I. Córdova-Guerrero、Lucía San Andrés、Alma E. Leal-Orozco、José M. Padrón、J.M. Cornejo-Bravo、Francisco León

  DOI：10.1016/j.tetlet.2013.06.048

  日期：2013.8

  A series of oxidized abietane diterpenes have been synthesized from 8,11,13-abietanotriene. The reaction of 6,7-dehydroferruginol methyl ether with dimethyldioxirane (DMDO) was carried out under various conditions. In all cases, the oxidation of positions C-6 and C-7 were observed with high selectivity when DMDO was used. When some reaction conditions, such as temperature and time were increased, 6 alpha-hydroxysugiol was obtained. Also an interesting formation of the cis aminol derivatives was synthesized from cis epoxide 12. (C) 2013 Elsevier Ltd. All rights reserved.
• In Vivo Biological Evaluation of a Synthetic Royleanone Derivative as a Promising Fast-Acting Trypanocidal Agent by Inducing Mitochondrial-Dependent Necrosis
  作者：Rubén Martín-Escolano、Juan J. Guardia、Javier Martín-Escolano、Nuria Cirauqui、Antonio Fernández、Maria J. Rosales、Rachid Chahboun、Manuel Sánchez-Moreno、Enrique Alvarez-Manzaneda、Clotilde Marín

  DOI：10.1021/acs.jnatprod.0c00651

  日期：2020.12.24

  The life-long and life-threatening Chagas disease is one of the most neglected tropical diseases caused by the protozoan parasite Trypanosoma cruzi. It is a major public health problem in Latin America, as six to seven million people are infected, being the principal cause of mortality in many endemic regions. Moreover, Chagas disease has become widespread due to migrant populations. Additionally, there are no vaccines nor effective treatments to fight the disease because of its long-term nature and complex pathology. Therefore, these facts emphasize how crucial the international effort for the development of new treatments against Chagas disease is. Here, we present the in vitro and in vivo trypanocidal activity of some oxygenated abietane diterpenoids and related compounds. The 1,4-benzoquinone 15, not yet reported, was identified as a fast-acting trypanocidal drug with efficacy against different strains in vitro and higher activity and lower toxicity than benznidazole in both phases of murine Chagas disease. The mode of action was also evaluated, suggesting that quinone 15 kills T. cruzi by inducing mitochondrion-dependent necrosis through a bioenergetics collapse caused by a mitochondrial membrane depolarization and iron-containing superoxide dismutase inhibition. Therefore, the abietane 1,4-benzoquinone 15 can be considered as a new candidate molecule for the development of an appropriate and commercially accessible anti-Chagas drug.
• Stereoselective synthesis of (−)-6,7-dehydroferruginyl methyl ether
  作者：Yonghong Gan、Anpai Li、Xinfu Pan、Albert S.C Chan、Teng-Kuei Yang

  DOI：10.1016/s0957-4166(00)00007-0

  日期：2000.2

  A stereoselective synthetic route to (-)-6,7-dehydroferruginyl methyl ether was developed from (S)-(-)-alpha-cyclocitral. (C) 2000 Elsevier Science Ltd. All rights reserved.