(13S,14RS)-8,13-epoxylabdane-14,15-diol | 357329-86-3

• 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: (13S,14RS)-8,13-epoxylabdane-14,15-diol
• 英文别名: tarapacol；8,13-epoxylabdane-14,15-diol；1-[(3S,4aR,6aS,10aS,10bR)-3,4a,7,7,10a-pentamethyl-2,5,6,6a,8,9,10,10b-octahydro-1H-benzo[f]chromen-3-yl]ethane-1,2-diol
• CAS: 357329-86-3
• 化学式: C₂₀H₃₆O₃
• 分子量: 324.504
• InChiKey: KYTFZACHEUSLEA-FMSLRJNNSA-N

物化性质

• 沸点：
  430.4±15.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (13S,14RS)-8,13-epoxylabdane-14,15-diol 在 过氧乙酸 、 sodium periodate 、 lithium aluminium tetrahydride 、 正丁基锂 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 19.0h， 生成 降龙涎香醚
  参考文献：
  名称：

  A PRACTICAL SYNTHESIS OF AMBROX® FROM SCLAREOL USING NO METALLIC OXIDANT

  摘要：

  The commercial synthesis of Ambrox((R)) is modified so that the key intermediate, the sclareolide, results from an indirect oxidative degradation of sclareol. This method allows to greatly alleviate the waste disposal problem and to raise the overall yield of Ambrox((R)) to 75%.

  DOI：

  10.1081/scc-100103265
• 作为产物：
  描述：

  香紫苏醇 在 过氧乙酸 、 sodium hydroxide 、 sodium acetate 作用下， 以 乙酸乙酯 、 叔丁醇 为溶剂， 反应 194.0h， 生成 (13S,14RS)-8,13-epoxylabdane-14,15-diol
  参考文献：
  名称：

  A PRACTICAL SYNTHESIS OF AMBROX® FROM SCLAREOL USING NO METALLIC OXIDANT

  摘要：

  The commercial synthesis of Ambrox((R)) is modified so that the key intermediate, the sclareolide, results from an indirect oxidative degradation of sclareol. This method allows to greatly alleviate the waste disposal problem and to raise the overall yield of Ambrox((R)) to 75%.

  DOI：

  10.1081/scc-100103265

文献信息

• A Short and Efficient Synthesis of (+)-13-Epimanoyl Oxide from Sclareol
  作者：Jean Moulines、Anne-Marie Lamidey、Jean-Paul Bats、Vincent Morisson

  DOI：10.1080/00397919308011142

  日期：1993.12

  (+)-13-Epimanoyl oxide has been synthesised in four steps from natural sclareol in an overall yield of 78%; preparation of the related labdane-14,15-diols is involved in this synthetic pathway.

  (+)-13-表没药烯酰氧化物已从天然没药烯醇经四步反应合成，总产率为78%；在这一合成路径中同时涉及了相关labdane-14,15-二醇的制备。
• Diterpenoids from Grindelia tarapacana
  作者：Lin Zhou、Eduardo R. Fuentes、Joseph J. Hoffmann、Barbara N. Timmermann

  DOI：10.1016/0031-9422(95)00419-8

  日期：1995.11

  Abstract Seven new and two known diterpenoids, as well as α-spinasterol, were isolated from Grindelia tarapacana. The new diterpenoids were fully characterized, on the basis of spectroscopic analysis and chemical evidence, as 14,15-dihydroxy-13-epi-manoyloxide (tarapacol), 15-acetoxy-14-hydroxy-13-epi-manoyloxide (tarapacol 15-acetate), 14,15-diacetoxy-13-epi-manoyloxide (tarapacol diacetate), 11α

  摘要 从 Grindelia tarapacana 中分离出 7 种新的和两种已知的二萜，以及 α-菠菜甾醇。根据光谱分析和化学证据，新的二萜类化合物被完全表征为 14,15-dihydroxy-13-epi-manoyloxide (tarapacol)、15-acetoxy-14-hydroxy-13-epi-manoyloxide (tarapacol 15-醋酸酯), 14,15-diacetoxy-13-epi-manoyloxide (tarapacol diacetate), 11α,14,15-trihydroxy-13-epi-manoyloxide (tarapacanol A), 14,15-diacetoxy-11α-hydroxy-13-epi -manoyloxide (tarapacanol A 14,15-dihydroxy-11-keto-13-epi-manoyloxide
• A PRACTICAL SYNTHESIS OF AMBROX® FROM SCLAREOL USING NO METALLIC OXIDANT
  作者：Jean Moulines、Anne-Marie Lamidey、Valérie Desvergnes-Breuil

  DOI：10.1081/scc-100103265

  日期：2001.1

  The commercial synthesis of Ambrox((R)) is modified so that the key intermediate, the sclareolide, results from an indirect oxidative degradation of sclareol. This method allows to greatly alleviate the waste disposal problem and to raise the overall yield of Ambrox((R)) to 75%.