iso-GA₃

• 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: iso-GA₃
• 英文别名: (1S,2S,3S,4R,7R,10R,13S,17R)-13,17-dihydroxy-4-methyl-14-methylidene-5-oxo-6-oxapentacyclo[11.2.1.14,7.01,10.03,9]heptadec-8-ene-2-carboxylic acid
• 化学式: C₁₉H₂₂O₆
• 分子量: 346.38
• InChiKey: SLSYEBAZQRZQID-QLGAMZAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  gibberellic acid 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 168.0h， 以51%的产率得到3-epi-gibberellic acid
  参考文献：
  名称：

  Improved Procedures for Direct Conversions of Natural 3b-Hydroxy-gibberellins to 3a-Hydroxy-and 3-Oxo-gibberellins

  摘要：

  Natural 3 beta-hydroxy-gibberellins, GA(3) (gibberellic acid) (1), GA(1) (2), and GA(4) (3), were directly converted to 3 alpha-hydroxy-gibberellins, 3-epi-GA(3) (4), -GA(1) (5) and -GA(4) (6), by highly alpha-biased equilibration through retro- and re-aldol mechanism with potassium tert-butoxide in tert-butyl alcohol, and to 3-oxo-gibberellins, 3-oxo-GA(95) (7), -GA(20) (8) and -GA(9) (9), by catalytic oxidation with tetrapropylammonium perruthenate.

  DOI：

  10.3987/com-98-8288

文献信息

• Improved Procedures for Direct Conversions of Natural 3b-Hydroxy-gibberellins to 3a-Hydroxy-and 3-Oxo-gibberellins
  作者：Hideharu Seto、Shozo Fujioka、Yuji Kamiya、Shigeo Yoshida

  DOI：10.3987/com-98-8288

  日期：——

  Natural 3 beta-hydroxy-gibberellins, GA(3) (gibberellic acid) (1), GA(1) (2), and GA(4) (3), were directly converted to 3 alpha-hydroxy-gibberellins, 3-epi-GA(3) (4), -GA(1) (5) and -GA(4) (6), by highly alpha-biased equilibration through retro- and re-aldol mechanism with potassium tert-butoxide in tert-butyl alcohol, and to 3-oxo-gibberellins, 3-oxo-GA(95) (7), -GA(20) (8) and -GA(9) (9), by catalytic oxidation with tetrapropylammonium perruthenate.