13-hydroxy-1-methyl-9-(4-methyl-3,5-dioxo-1,2,4-triazolin-1-yl)-8-phenylhexacyclo<6.5.1.0^2,7.0^4,12.0^5,10.0^9,13>tetradec-9(13)-ene-3,6-dione

• 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: 13-hydroxy-1-methyl-9-(4-methyl-3,5-dioxo-1,2,4-triazolin-1-yl)-8-phenylhexacyclo<6.5.1.0^2,7.0^4,12.0^5,10.0^9,13>tetradec-9(13)-ene-3,6-dione
• 英文别名: 1-(13-Hydroxy-1-methyl-3,6-dioxo-8-phenyl-9-hexacyclo[6.5.1.02,7.04,12.05,10.09,13]tetradecanyl)-4-methyl-1,2,4-triazolidine-3,5-dione；1-(13-hydroxy-1-methyl-3,6-dioxo-8-phenyl-9-hexacyclo[6.5.1.02,7.04,12.05,10.09,13]tetradecanyl)-4-methyl-1,2,4-triazolidine-3,5-dione
• 化学式: C₂₄H₂₃N₃O₅
• 分子量: 433.464
• InChiKey: YATQZWRFYPGKNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-甲基-1,2,4-三吖戊啶-3,5-二酮 、 1-methyl-8-phenyl-hexacyclo<6.5.1.0^2,7.0^4,12.0^5,10.0^9,13>tetradec-9(13)-ene-3,6-dione 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 以35%的产率得到13-hydroxy-1-methyl-9-(4-methyl-3,5-dioxo-1,2,4-triazolin-1-yl)-8-phenylhexacyclo<6.5.1.0^2,7.0^4,12.0^5,10.0^9,13>tetradec-9(13)-ene-3,6-dione
  参考文献：
  名称：

  Synthesis, Structure, and Properties of Twofold Bridged Sesquinorbornenes

  摘要：

  The twofold bridged sesquinorbornenes 2 and 6 were prepared using sequential [4 + 2] cycloadditions of benzoquinone with 1,5-dihydropentalenes 1 and 5. These syntheses were improved using dilution conditions or a more reactive substituted benzoquinone. Results from semiempirical and ab initio DFT calculations indicated remarkably high pyramidalization angles (phi = 46-47 degrees) for the central C-C double-bond atoms. The chemical reactivity with triplet and singlet oxygen, dimethyldioxirane and N-methyl-1,2,4-triazoline-3,5-dione supports these structural assignments.

  DOI：

  10.1002/(sici)1099-0690(199809)1998:9<1759::aid-ejoc1759>3.0.co;2-i

文献信息

• Synthesis, Structure, and Properties of Twofold Bridged Sesquinorbornenes
  作者：Axel G. Griesbeck、Thomas Deufel、Georg Hohlneicher、Rupert Rebentisch、Jörg Steinwascher

  DOI：10.1002/(sici)1099-0690(199809)1998:9<1759::aid-ejoc1759>3.0.co;2-i

  日期：1998.9

  The twofold bridged sesquinorbornenes 2 and 6 were prepared using sequential [4 + 2] cycloadditions of benzoquinone with 1,5-dihydropentalenes 1 and 5. These syntheses were improved using dilution conditions or a more reactive substituted benzoquinone. Results from semiempirical and ab initio DFT calculations indicated remarkably high pyramidalization angles (phi = 46-47 degrees) for the central C-C double-bond atoms. The chemical reactivity with triplet and singlet oxygen, dimethyldioxirane and N-methyl-1,2,4-triazoline-3,5-dione supports these structural assignments.