ent-1α-deuterio-2β,13-diacetoxy-3α,10β-dihydroxy-20-norgibberell-16-ene-7,19-dioic acid 7-methyl ester-19,10-lactone | 193823-03-9

• 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: ent-1α-deuterio-2β,13-diacetoxy-3α,10β-dihydroxy-20-norgibberell-16-ene-7,19-dioic acid 7-methyl ester-19,10-lactone
• CAS: 193823-03-9
• 化学式: C₂₄H₃₀O₉
• 分子量: 463.489
• InChiKey: KVOVTRDDBXYFPZ-RKCODICMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 重原子数：
  33.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  125.43
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  ent-1α-deuterio-2β,13-diacetoxy-3α,10β-dihydroxy-20-norgibberell-16-ene-7,19-dioic acid 7-methyl ester-19,10-lactone 在 吡啶 、 偶氮二异丁腈 、 sodium methylate 、 4-甲基苯磺酸吡啶 、 氘代三正丁基锡 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 17.25h， 生成 ent-1α,2β-dideuterio-13-acetoxy-3α,10β-dihydroxy-20-norgibberell-16-ene-7,19-dioic acid 7-methyl ester-19,10-lactone
  参考文献：
  名称：

  Partial Synthesis of [1β,2α,17,17-D4] Gibberellin A1

  摘要：

  An efficient route for an alternative synthesis of gibberellin A(1) from gibberellin A(3) is described. Based on iodolactonisation the method provides access to gibberellin A(1) labeled by deuterium with both high incorporation of the isotope and high stereoselectivity at the positions 1 beta and 2 alpha. The additional deuterium labeling at C-17 was introduced via the corresponding 16-norketone resulting in [1 beta,2 alpha,17,17-D-4] gibberellin A(1).

  DOI：

  10.1002/prac.19973390178
• 作为产物：
  描述：

  ent-2β,13-Diacetoxy-3α,10β-dihydroxy-1α-iodo-20-norgibberell-16-ene-7,19-dioic Acid 19,10-Lactone 7-Methyl Ester 在 偶氮二异丁腈 、 氘代三正丁基锡 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以87%的产率得到ent-1α-deuterio-2β,13-diacetoxy-3α,10β-dihydroxy-20-norgibberell-16-ene-7,19-dioic acid 7-methyl ester-19,10-lactone
  参考文献：
  名称：

  Partial Synthesis of [1β,2α,17,17-D4] Gibberellin A1

  摘要：

  An efficient route for an alternative synthesis of gibberellin A(1) from gibberellin A(3) is described. Based on iodolactonisation the method provides access to gibberellin A(1) labeled by deuterium with both high incorporation of the isotope and high stereoselectivity at the positions 1 beta and 2 alpha. The additional deuterium labeling at C-17 was introduced via the corresponding 16-norketone resulting in [1 beta,2 alpha,17,17-D-4] gibberellin A(1).

  DOI：

  10.1002/prac.19973390178