(4aS,10aS)-6-methoxy-1,1,4a-trimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-9-ol | 269719-14-4

• 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)-6-methoxy-1,1,4a-trimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-9-ol
• CAS: 269719-14-4
• 化学式: C₂₁H₃₂O₂
• 分子量: 316.484
• InChiKey: KLADMMATBMDROH-QJUSXVFHSA-N

物化性质

• 沸点：
  434.3±45.0 °C(predicted)
• 密度：
  1.012±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

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：
  0.71
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4aS,10aS)-6-methoxy-1,1,4a-trimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-9-ol 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以79%的产率得到(4aS,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,10a-hexahydrophenanthrene
  参考文献：
  名称：

  New strategy toward the diverted synthesis of oxidized abietane diterpenes via oxidation of 6,7-dehydroferruginol methyl ether with dimethyldioxirane

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2013.06.048
• 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 12.0h， 生成 (4aS,10aS)-6-methoxy-1,1,4a-trimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-9-ol
  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 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.
• 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.