(2aS,5aS,8aR,8bR)-十氢-2,2,5a,8a-四甲基-2H-萘并[1,8-bc]呋喃 | 53625-18-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 中文名称: (2aS,5aS,8aR,8bR)-十氢-2,2,5a,8a-四甲基-2H-萘并[1,8-bc]呋喃
• 英文名称: (-)-maalioxide
• 英文别名: 2,2,5a,8a-Tetramethyldecahydro-2H-naphtho[1,8-bc]furan；(1R,4S,8S)-1,3,3,8-tetramethyl-2-oxatricyclo[6.3.1.04,12]dodecane
• CAS: 53625-18-6
• 化学式: C₁₅H₂₆O
• 分子量: 222.371
• InChiKey: PZKNYJWHOZUWDF-YPRXJGMQSA-N

物化性质

• LogP：
  4.850 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2aS,5aS,8aR,8bR)-十氢-2,2,5a,8a-四甲基-2H-萘并[1,8-bc]呋喃 在 Aspergillus cellulosae 、 Czapek-pepton medium 作用下， 反应 48.0h， 以29.9%的产率得到7β-Hydroxymaalioxide
  参考文献：
  名称：

  Biotransformation of (-)-Maalioxide by Aspergillus niger and Aspergillus cellulosae

  摘要：

  A sesquiterpene cyclic ether, (-)-maalioxide (1) from the liverwort Plagiochila sciophila was biotransformed by Aspergillus niger and A. cellulosae to afford the structurally interesting compounds. The stereostructures of the metabolites were established by a combination of high resolution NMR spectrum, X-Ray crystallographic analysis and the chemical reaction.

  DOI：

  10.3987/com-03-s(p)59

文献信息

• The Reaction of Three Sesquiterpene Ethers with<i>m</i>-Chloroperbenzoic Acid
  作者：Motoo Tori、Masakazu Sono、Yoshinori Asakawa

  DOI：10.1246/bcsj.63.1770

  日期：1990.6

  Three sesquiterpene ethers, guaioxide, a guaiane-type sesquiterpene ether (LB), and maalioxide have been subjected to reaction with m-chloroperbenzoic acid in chloroform under reflux. Guaioxide afforded four tertiary alcohols, while other two gave secondary alcohols. Structures of the products were determined by spectral data and chemical correlations.

  三种倍半萜醚、愈创木酚、愈创木烷类倍半萜醚（LB）和马林酸在氯仿中与间氯过氧苯甲酸发生反应。愈创木酚产生了四种叔醇，而其他两种则产生了仲醇。通过光谱数据和化学相关性确定了产物的结构。
• Biotransformation of (-)-Maalioxide by Aspergillus niger and Aspergillus cellulosae
  作者：Toshihiro Hashimoto、Yoshiaki Noma、Yoshiaki Gotoh、Masami Tanaka、Shigeru Takaoka、Yoshinori Asakawa

  DOI：10.3987/com-03-s(p)59

  日期：——

  A sesquiterpene cyclic ether, (-)-maalioxide (1) from the liverwort Plagiochila sciophila was biotransformed by Aspergillus niger and A. cellulosae to afford the structurally interesting compounds. The stereostructures of the metabolites were established by a combination of high resolution NMR spectrum, X-Ray crystallographic analysis and the chemical reaction.