(4aS,9R,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-9-carboxylic acid | 337909-72-5

• 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,9R,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-9-carboxylic acid
• CAS: 337909-72-5
• 化学式: C₂₂H₃₂O₃
• 分子量: 344.494
• InChiKey: DGMCGTZGDNRVAW-GTCCEBARSA-N

物化性质

• 沸点：
  477.5±45.0 °C(Predicted)
• 密度：
  1.051±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4aS,9R,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-9-carboxylic acid 在 palladium on activated charcoal lead(IV) acetate 、 copper diacetate 、 氢气 、 三溴化硼 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 喹啉 、 甲醇 、 二氯甲烷 、 氯仿 、 水 、 乙酸乙酯 为溶剂， 反应 62.5h， 生成 罗列酮
  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：

  2-氯丙烷 、 (4aS,9R,10aS)-6-Methoxy-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-9-carboxylic acid 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 以80.9%的产率得到(4aS,9R,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-9-carboxylic acid
  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