(+)-sempervirol | 17990-27-1

• 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: (+)-sempervirol
• 英文别名: sempervirol；empervirol；(4bS,8aS)-4b,8,8-trimethyl-3-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-2-ol
• CAS: 17990-27-1
• 化学式: C₂₀H₃₀O
• 分子量: 286.458
• InChiKey: RSIJAQZNHHXEJZ-AZUAARDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  21
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+)-sempervirol 、 乙酸酐 以 吡啶 为溶剂， 反应 16.0h， 以100%的产率得到(+)-sempervirol acetate
  参考文献：
  名称：

  Chemoenzymatic synthesis of (+)-totarol, (+)-podototarin, (+)-sempervirol, and (+)-jolkinolides E and D

  摘要：

  The enzymatic resolution products [(1R,4aR,8aR)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo-trans-naphthalene-1-methanol-2-ethylene acetal (8aR)-7 (98% ee) and {acetate of (IS,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo-trans-naphthalene-1-methanol-2-ethylene acetal} (8aS)-9 (>99% ee)] obtained by the lipase-catalyzed enantioselective acetylation of (+/-)-7 in the presence of vinyl acetate as an acyl donor were converted to the alpha,beta-unsaturated ketones (8aR)-6 and (8aS)-6, respectively. Concise syntheses of (+)-totarol 1, (+)-podototarin 2 and (+)-sempervirol 3 were achieved based on Michael reactions between (8aS)-6 and the appropriate P-keto ester followed by aldol condensation. The first chiral syntheses of (+)-jolkinolides E 4 and D 5 were achieved from (5R,10R,12R)-12-hydroxypodocarpa-8(14)-en-13-one 15 derived from (8aR)-6. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.11.024
• 作为产物：
  描述：

  (S)-α-Cyclogeraniol 在 palladium on activated charcoal 三氯化铝 、 磷酸 、 氢气 、 三溴化硼 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 、 苯 为溶剂， 生成 (+)-sempervirol
  参考文献：
  名称：

  (+)-Ferruginol、(+)-Sempervirol 和 (+)-Podocarpa-8(14)-en-13-one 的简单全合成

  摘要：

  (R)-(-)-α-环柠檬醛与（3-异丙基-4-甲氧基苄基）-、（4-异丙基-3-甲氧基苄基）-和（3-甲氧基苄基）三苯基氯化鏻的Wittig反应得到苯乙烯基衍生物其部分氢化成相应的二氢衍生物（18、26和27）。18 和 26 用无水氯化铝分子内环化，然后用三溴化硼去甲基化得到 (+)-ferruginol 和 (+)-sempervirol。27 的类似环化得到 (+)-13-甲氧基podocarpa-8, 11, 13-triene。在乙醇存在下用液氨中的锂将其还原，然后用稀盐酸处理得到 (+)-podocarpa-8(14)-en-13-one，这是一种用于天然二萜合成的通用中间体。

  DOI：

  10.1246/bcsj.52.212

文献信息

• JPH01311020A
  申请人：——

  公开号：JPH01311020A

  公开（公告）日：1989-12-15
• [EN] ANTHELMINTIC COMPOUNDS<br/>[FR] COMPOSÉS ANTHELMINTIQUES
  申请人：UNIV ABERYSTWYTH

  公开号：WO2016097759A1

  公开（公告）日：2016-06-23

  The present invention relates to compounds, in particular derivatives of the diterpenoids sempervirol and 7‐keto‐sempervirol, and their use in therapy, including in pharmaceutical compositions and combinations, especially in the treatment and/or prophylaxis of the tropical diseases schistosomiasis and/or fascioliasis, for example in humans or in non‐human land mammals such as sheep, cattle, other ruminants, or goats.
• Chemoenzymatic synthesis of (+)-totarol, (+)-podototarin, (+)-sempervirol, and (+)-jolkinolides E and D
  作者：Takahiro Miyake、Hideo Kigoshi、Hiroyuki Akita

  DOI：10.1016/j.tetasy.2007.11.024

  日期：2007.12

  The enzymatic resolution products [(1R,4aR,8aR)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo-trans-naphthalene-1-methanol-2-ethylene acetal (8aR)-7 (98% ee) and acetate of (IS,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo-trans-naphthalene-1-methanol-2-ethylene acetal} (8aS)-9 (>99% ee)] obtained by the lipase-catalyzed enantioselective acetylation of (+/-)-7 in the presence of vinyl acetate as an acyl donor were converted to the alpha,beta-unsaturated ketones (8aR)-6 and (8aS)-6, respectively. Concise syntheses of (+)-totarol 1, (+)-podototarin 2 and (+)-sempervirol 3 were achieved based on Michael reactions between (8aS)-6 and the appropriate P-keto ester followed by aldol condensation. The first chiral syntheses of (+)-jolkinolides E 4 and D 5 were achieved from (5R,10R,12R)-12-hydroxypodocarpa-8(14)-en-13-one 15 derived from (8aR)-6. (c) 2007 Elsevier Ltd. All rights reserved.
• A Simple Total Synthesis of (+)-Ferruginol, (+)-Sempervirol, and (+)-Podocarpa-8(14)-en-13-one
  作者：Takashi Matsumoto、Shuji Usui

  DOI：10.1246/bcsj.52.212

  日期：1979.1

  derivatives (18, 26, and 27). Intramolecular cyclization of 18 and 26 with anhydrous aluminium chloride followed by demethylation with boron tribromide gave (+)-ferruginol and (+)-sempervirol. The similar cyclization of 27 gave (+)-13-methoxypodocarpa-8, 11, 13-triene. This was reduced with lithium in liquid ammonia in the presence of ethanol and then treated with dilute hydrochloric acid to give (+)-podo

  (R)-(-)-α-环柠檬醛与（3-异丙基-4-甲氧基苄基）-、（4-异丙基-3-甲氧基苄基）-和（3-甲氧基苄基）三苯基氯化鏻的Wittig反应得到苯乙烯基衍生物其部分氢化成相应的二氢衍生物（18、26和27）。18 和 26 用无水氯化铝分子内环化，然后用三溴化硼去甲基化得到 (+)-ferruginol 和 (+)-sempervirol。27 的类似环化得到 (+)-13-甲氧基podocarpa-8, 11, 13-triene。在乙醇存在下用液氨中的锂将其还原，然后用稀盐酸处理得到 (+)-podocarpa-8(14)-en-13-one，这是一种用于天然二萜合成的通用中间体。