6β-hydroxy-(1α,10β),(4β,5α)-diepoxygermacrane | 831176-56-8

• 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: 6β-hydroxy-(1α,10β),(4β,5α)-diepoxygermacrane
• 英文别名: 1α,10β,4β,5α-diepoxy-7αH-germacran-6β-ol；(1S,4S,6R,7R,8S,11R)-4,11-dimethyl-8-propan-2-yl-5,12-dioxatricyclo[9.1.0.04,6]dodecan-7-ol
• CAS: 831176-56-8
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: CZZAIHWBOUXBPS-TVDPOAAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6β-acetoxy-(1α,10β),(4β,5α)-diepoxygermacrane 在 BEM medium 作用下， 以 乙醇 、 水 为溶剂， 反应 168.0h， 以8%的产率得到6β-hydroxy-(1α,10β),(4β,5α)-diepoxygermacrane
  参考文献：
  名称：

  Enzyme-Catalyzed Rearrangement of a Diepoxy-germacrane Compound into New 7-epi-Eudesmane Derivatives

  摘要：

  Two new 7-epi-eudesmane derivatives, together with two new germacrane compounds, have been isolated from the microbial-transformation of a (1alpha,10beta),(4beta,5alpha)-diepoxygermacrane using the hydroxylating fungi Rhizopus nigricans. The rearranged skeleton and the stereochemistry of the chiral centers have been determined by means of their spectral data, and the absolute configuration has been confirmed by single-crystal X-ray analyses. A possible mechanism based on an enzyme-catalyzed isomerization to a 1alpha-hydroxy-(4beta,5alpha)-epoxygermacr-9(E)-ene intermediate and a subsequent cyclization process is proposed in order to explain the formation of the 7-epi-eudesmane compounds.

  DOI：

  10.1021/jo048783k

文献信息

• A germacrane derivative from Pallenis spinosa
  作者：Juan F. Sanz、J.Alberto Marco

  DOI：10.1016/0031-9422(91)85146-q

  日期：1991.1

  Abstract Extraction of aerial parts of Pallenis spinosa and chromatographic separation have yielded a new germacrane derivative and the known sesquiterpenes shiromool and α-cadinol.

  摘要 提取刺参的地上部分并进行色谱分离，得到了一种新的锗烷衍生物和已知的倍半萜类 shiromool 和 α-cadinol。
• Enzyme-Catalyzed Rearrangement of a Diepoxy-germacrane Compound into New 7-<i>epi</i>-Eudesmane Derivatives
  作者：Andrés García-Granados、María C. Gutiérrez、Antonio Martínez、Francisco Rivas

  DOI：10.1021/jo048783k

  日期：2005.1.1

  Two new 7-epi-eudesmane derivatives, together with two new germacrane compounds, have been isolated from the microbial-transformation of a (1alpha,10beta),(4beta,5alpha)-diepoxygermacrane using the hydroxylating fungi Rhizopus nigricans. The rearranged skeleton and the stereochemistry of the chiral centers have been determined by means of their spectral data, and the absolute configuration has been confirmed by single-crystal X-ray analyses. A possible mechanism based on an enzyme-catalyzed isomerization to a 1alpha-hydroxy-(4beta,5alpha)-epoxygermacr-9(E)-ene intermediate and a subsequent cyclization process is proposed in order to explain the formation of the 7-epi-eudesmane compounds.