(4bS,8aS)-4b,6,7,8,8a,10-hexahydro-3-methoxy-4b,8,8-trimethyl-2-(1-methylethyl)phenanthren-9(5H)-one | 70614-88-9

• 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: (4bS,8aS)-4b,6,7,8,8a,10-hexahydro-3-methoxy-4b,8,8-trimethyl-2-(1-methylethyl)phenanthren-9(5H)-one
• 英文别名: (4bS,8aS)-3-methoxy-4b,8,8-trimethyl-2-propan-2-yl-6,7,8a,10-tetrahydro-5H-phenanthren-9-one
• CAS: 70614-88-9
• 化学式: C₂₁H₃₀O₂
• 分子量: 314.468
• InChiKey: NJNCWIUSRJLZEH-PZJWPPBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4bS,8aS)-4b,6,7,8,8a,10-hexahydro-3-methoxy-4b,8,8-trimethyl-2-(1-methylethyl)phenanthren-9(5H)-one 在 lithium aluminium tetrahydride 、 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 6β-hydroxyferruginol
  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：

  (4aS,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,10a-hexahydrophenanthrene 在 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 6.5h， 生成 (4bS,8aS)-4b,6,7,8,8a,10-hexahydro-3-methoxy-4b,8,8-trimethyl-2-(1-methylethyl)phenanthren-9(5H)-one
  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

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。
• Synthesis of variously oxidized abietane diterpenes and their antibacterial activities against MRSA and VRE
  作者：Zhixiang Yang、Yoshikazu Kitano、Kazuhiro Chiba、Naohiro Shibata、Hiroshi Kurokawa、Yohei Doi、Yoshichika Arakawa、Masahiro Tada

  DOI：10.1016/s0968-0896(00)00253-4

  日期：2001.2

  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.