(4bS,8aS,9R,10S)-4b,8,8-trimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthrene-3,9,10-triol | 111197-59-2

• 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,9R,10S)-4b,8,8-trimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthrene-3,9,10-triol
• CAS: 111197-59-2
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: XOPWASSJNBNHRW-CGBFIWBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ar-abietatriene 在 chromium(VI) oxide 、 aluminum (III) chloride 、 sodium tetrahydroborate 、 二甲基二环氧乙烷 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 、 甲基磺酰氯 、 三乙胺 、 间氯过氧苯甲酸 、 lithium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 73.75h， 生成 (4bS,8aS,9R,10S)-4b,8,8-trimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthrene-3,9,10-triol
  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

文献信息

• 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.