异降补身酮 | 51020-10-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 异降补身酮
• 英文名称: (-)-(8aS)-3,4a,8,8-tetramethyl-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one
• 英文别名: (4aR,8aS)-3,4a,8,8-tetramethyl-4a,5,6,7,8,8a-hexahydronaphthalen-2(1H)-one；isonordrimenone；nordrimenone；(4aR)-3,4a,8,8-tetramethyl-(4ar,8at)-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one；(4aR)-3,4a,8,8-Tetramethyl-(4ar,8at)-4a,5,6,7,8,8a-hexahydro-1H-naphthalin-2-on；Isonordrimenon；(4aR,8aS)-3,4a,8,8-tetramethyl-5,6,7,8a-tetrahydro-1H-naphthalen-2-one
• CAS: 51020-10-1
• 化学式: C₁₄H₂₂O
• 分子量: 206.328
• InChiKey: FXFDPILDESFQAO-GXTWGEPZSA-N

物化性质

• 稳定性/保质期：

  存在于白肋烟和香料烟的烟叶中。

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

制备方法与用途

合成制备方法

• 烟草：OR57，OR26。

反应信息

• 作为反应物：
  描述：

  异降补身酮 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以24.8%的产率得到(5S,8R,9R,10S)-4,4,8α,10β-tetramethyloctahydronaphtho[8,9-β]oxiren-7-one
  参考文献：
  名称：

  Comparative Study on the Larvicidal Activity of Drimane Sesquiterpenes and Nordrimane Compounds against Drosophila melanogaster til-til

  摘要：

  Natural compounds from Drimys winteri Forst and derivatives exhibited larvicidal effects against Drosophila melanogaster til-til. The most active compound was isodrimenin (4). The highest lethal concentration to the larvae of D. melanogaster was 4.5 +/- 0.8 mg/L. At very low concentrations drimenol (1), confertifolin (3), and drimanol (5) displayed antifeedant and larvae growth regulatory activity. The antifeedant results of nordrimanic and drimanic compounds were better in first instar larvae. The EC50 value of polygodial (2) was 60.0 +/- 4.2 mg/L; of diol 15 45.0 +/- 2.8 mg/L, and of diol 17 36.9 +/- 3.7 mg/L, while the new nordrimane compound 12 presented a value of 83.2 +/- 3.5 mg/L.

  DOI：

  10.3390/molecules18044192
• 作为产物：
  描述：

  (-)-补身醇 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到异降补身酮
  参考文献：
  名称：

  Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies

  摘要：

  包括多神烯（1）、异多神烯（2）、神烯醇（3）和聚合萜（4）在内的十七种天然来源的化合物，以及从1-3合成的半合成衍生物5-17，进行了体外抗真菌活性评估，使用了标准化程序和两个终点（MIC100和MIC50）对一组特定真菌进行了测试。通过构象和电子研究支持的整个系列SAR分析表明，Δ7,8-双键可能是与抗真菌活性相关的关键结构特征。活性化合物的MEP在Δ7,8-双键附近显示出明显的负值最小值（深红区域），而在无活性化合物中没有出现。除了这个负区，1中出现了一个正区域（深蓝），而在其对映体2及其他活性化合物中则未观察到。活性化合物的LogP值在2.33到3.84之间变化，但MIC的差异与LogP值的相关变化并不相符。

  DOI：

  10.3390/molecules18022029

文献信息

• A revised structure for nordrimenone
  作者：C. J. W. Brooks、G. Lindsay、K. H. Overton

  DOI：10.1039/j39700000203

  日期：——

  Nordrimenone, previously thought to have the hexahydronaphthalen-2(1H)-one structure (1), has been shown to be the hexahydronaphthalen-1 (4H)-one (4).

  以前被认为具有六氢萘-2（1 H）-one结构（1）的诺德美奈酮已被证明是六氢萘-1（4 H）-one（4）。
• LTA-mediated synthesis and complete assignment of1H and13C NMR data of two natural 11-nordrimanes: isonordrimenone and polygonone
  作者：Luis Moreno-Osorio、Luis Espinoza、Mauricio Cuellar、Marcelo Preite

  DOI：10.1002/mrc.2067

  日期：2007.11

  Two naturally occurring 11‐nordrimanes were synthesized, and their 1H and 13C NMR spectra were unambiguously assigned in full for the first time. Copyright © 2007 John Wiley & Sons, Ltd.

  合成了两种天然存在的 11-nordrimanes，并首次对它们的 1H 和 13C NMR 谱进行了明确指定。版权所有 © 2007 John Wiley & Sons, Ltd.
• Synthesis of Potential Ambra Odorants: 5,5,9-trimethyldecalyl derivatives
  作者：Günther Ohloff、Ferdinand Näf、René Decorzant、Walter Thommen、Erling Sundt

  DOI：10.1002/hlca.19730560425

  日期：1973.4.25

  AbstractThe synthesis of racemic stereoisomeric compounds with the 5,5,9‐trimethyldecalin skeleton and an oxygen function at C(1), C(2), or C(3) is describedAlthough racemic decalins are described, only the enantiomer related to steroids is drawn. The projection of the decalins was chosen so as to place the angular methyl group above the plane of the molecule and the oxygen function at C(1), C(2) or C(3) on the left side, as represented by formula 1–6. The relative configuration of the substituents in decalins is designated by using the convention of the steroid series: β, meaning on the same side as the angular methyl group at C(9) and α, meaning on the side opposite from the angular methyl group. The prefix cis or trans refers to the fusion of the decalin ring system, not to the position of the substituents. . A novel general one‐step synthesis of 2‐decalones by means of acid catalyzed cyclization of acyclic or monocyclic precursors has been developed.
• Hlubucek,J.R. et al., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1974, vol. 28, p. 18 - 22
  作者：Hlubucek,J.R. et al.

  DOI：——

  日期：——
• 673. The constitution and stereochemistry of drimenol, a novel bicyclic sesquiterpenoid
  作者：H. H. Appel、C. J. W. Brooks、K. H. Overton

  DOI：10.1039/jr9590003322

  日期：——