(relativ-1'R,2'S,5'S,6'S,9'R,10'S)-1'-Hydroxy-2',10'-dimethyl-7',11'-dioxo-4,5-dihydro-8'-oxa-pyrazol-(3-spiro-6')-tricyclo<8.3.0.0^5,9>tridecan | 22419-82-5

• 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: (relativ-1'R,2'S,5'S,6'S,9'R,10'S)-1'-Hydroxy-2',10'-dimethyl-7',11'-dioxo-4,5-dihydro-8'-oxa-pyrazol-(3-spiro-6')-tricyclo<8.3.0.0^5,9>tridecan
• 英文别名: (3S)-6a-hydroxy-6t,9a-dimethyl-(3r,3ac,6ac,9at,9bc)-4,5,6,6a,7,8,9a,9b,4',5'-decahydro-3aH-spiro[azuleno[4,5-b]furan-3,3'-pyrazole]-2,9-dione；(3'aS,5S,6'S,6'aR,9'aS,9'bR)-6'a-hydroxy-6',9'a-dimethylspiro[3,4-dihydropyrazole-5,3'-4,5,6,7,8,9b-hexahydro-3aH-azuleno[8,7-b]furan]-2',9'-dione
• CAS: 22419-82-5
• 化学式: C₁₆H₂₂N₂O₄
• 分子量: 306.362
• InChiKey: VSNARTKZYHDPOE-DIHQDQGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  88.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 冠裸穗豚草素 以 甲醇 、 乙醚 为溶剂， 以88%的产率得到
  参考文献：
  名称：

  The stereochemistry of the 1,3-dipolar cycloadditions of diazomethane to pseudoguaianolides

  摘要：

  The 1,3-dipolar cycloaddition of diazomethane to the sesquiterpene lactones, parthenin, coronopilin, and psilostachyin, gave their respective spiropyrazolines with complete chemoselectivity, while the diastere-oselectivity in favour of the (11S)-stereoisomer was 86-98%. Similarly, mexicanin I acetate, helenalin, and helenalin acetate provided the (11R)-diastereoisomer. When helenalin and its acetate were treated with a large excess of diazomethane, they afforded their respective dipyrazolines with 98% diastere-oselectivity in favour of the (2R,3S,11R)-diastereoisomer. All compounds were characterized by their physical and spectroscopic properties and their absolute configuration was established by X-ray diffraction analysis calculating the Flack and Hooft parameters. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.01.009