2β,4a,7-trihydroxy-1-methyl-8-methylene-(3ξ,4ξ)-4,5'-dihydro-3H-gibbano[4,3-c]pyrazole-1α,10β-dicarboxylic acid 1->4a-lactone 10-methyl ester | 109081-83-6

• 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: 2β,4a,7-trihydroxy-1-methyl-8-methylene-(3ξ,4ξ)-4,5'-dihydro-3H-gibbano[4,3-c]pyrazole-1α,10β-dicarboxylic acid 1->4a-lactone 10-methyl ester
• CAS: 109081-83-6
• 化学式: C₂₁H₂₆N₂O₆
• 分子量: 402.447
• InChiKey: SFWUJGMZHHDUPT-XAVAIKDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.01
• 重原子数：
  29.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  117.78
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2β,4a,7-trihydroxy-1-methyl-8-methylene-(3ξ,4ξ)-4,5'-dihydro-3H-gibbano[4,3-c]pyrazole-1α,10β-dicarboxylic acid 1->4a-lactone 10-methyl ester 在 Bartlett-Loesung 作用下， 反应 10.0h， 以38%的产率得到
  参考文献：
  名称：

  Regio- und stereospezifische Addition von Diazomethan an Gibberellins�ure: Ein neuer effektiver Weg zu 1,2-Methylengibberellinen

  摘要：

  A new pathway to 1-alpha,2-alpha-methylenegibberellines via pyrazoline intermediates is reported. In contrast to the addition of diazomethane to the DELTA-1-double bond of corresponding enones in the case of 1 "Umpolung" of the regioselectivity with cis-addition from the a-side to give pyrazoline ester 4 is observed. Subsequent photolysis of 4 leads to the 1,2-cyclopropyl derivative 6. The structures of the key compounds 4 and 6 are confirmed especially by n.m.r. and X-Ray analysis.

  DOI：

  10.1002/prac.19923340305
• 作为产物：
  描述：

  重氮甲烷 、 gibberellic acid 以 甲醇 、 乙醚 为溶剂， 反应 14.0h， 以66%的产率得到2β,4a,7-trihydroxy-1-methyl-8-methylene-(3ξ,4ξ)-4,5'-dihydro-3H-gibbano[4,3-c]pyrazole-1α,10β-dicarboxylic acid 1->4a-lactone 10-methyl ester
  参考文献：
  名称：

  Regio- und stereospezifische Addition von Diazomethan an Gibberellins�ure: Ein neuer effektiver Weg zu 1,2-Methylengibberellinen

  摘要：

  A new pathway to 1-alpha,2-alpha-methylenegibberellines via pyrazoline intermediates is reported. In contrast to the addition of diazomethane to the DELTA-1-double bond of corresponding enones in the case of 1 "Umpolung" of the regioselectivity with cis-addition from the a-side to give pyrazoline ester 4 is observed. Subsequent photolysis of 4 leads to the 1,2-cyclopropyl derivative 6. The structures of the key compounds 4 and 6 are confirmed especially by n.m.r. and X-Ray analysis.

  DOI：

  10.1002/prac.19923340305