ent-3α,13-diacetoxy-19-hydroxy-20-norgibberell-1(10),16-dien-7-oic acid, 7-methyl ester | 153401-06-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: ent-3α,13-diacetoxy-19-hydroxy-20-norgibberell-1(10),16-dien-7-oic acid, 7-methyl ester
• CAS: 153401-06-0
• 化学式: C₂₄H₃₂O₇
• 分子量: 432.514
• InChiKey: WSVOBPQLIMRPDW-KQWKSFQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  99.13
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ent-3α,13-diacetoxy-19-hydroxy-20-norgibberell-1(10),16-dien-7-oic acid, 7-methyl ester 在 α-azoisobutyronitrile 、 碘 、 丁基锡烷 、 sodium carbonate 作用下， 以 正己烷 、 乙腈 为溶剂， 反应 3.0h， 生成 ent-3α,13-diacetoxy-19,10β-epoxy-20-norgibberell-16-ene-7-oic acid, 7-methyl ester
  参考文献：
  名称：

  Synthesis, stability and biological activity of 19-desoxy-gibberellins A1 and A3

  摘要：

  The synthetic conversion of gibberellin A3 (GA3) to the 19-desoxy-derivatives of GA1 and GA3 is described. The key steps involve regiospecific reduction of the known GA3 hydrogenolysis product at the C-19 carboxyl group via treatment of the acyl chloride with zinc borohydride, followed by an iodocyclization of the resultant alcohol. 19-Desoxy-GA1 and GA3 are stable in alkali, unlike their parent lactones GA1 and GA3. Both derivatives are biologically active in inducing alpha-amylase production in protoplasts of Avena fatua aleurone. They have biological activities of one order of magnitude less than that of the natural analogues. These data reveal the significant contribution of the lactone carbonyl to the observed response (receptor affinity) of GA1 and GA3.

  DOI：

  10.1016/0031-9422(91)80004-k
• 作为产物：
  描述：

  methyl 4α-carboxy-3β,13α-dihydroxy-4β-methyl-16-methylenegibb-1-ene-6β-carboxylate 在 sodium tetrahydroborate 、 草酰氯 、 对甲苯磺酸 、 N,N-二甲基甲酰胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 5.0h， 生成 ent-3α,13-diacetoxy-19-hydroxy-20-norgibberell-1(10),16-dien-7-oic acid, 7-methyl ester
  参考文献：
  名称：

  Synthesis, stability and biological activity of 19-desoxy-gibberellins A1 and A3

  摘要：

  The synthetic conversion of gibberellin A3 (GA3) to the 19-desoxy-derivatives of GA1 and GA3 is described. The key steps involve regiospecific reduction of the known GA3 hydrogenolysis product at the C-19 carboxyl group via treatment of the acyl chloride with zinc borohydride, followed by an iodocyclization of the resultant alcohol. 19-Desoxy-GA1 and GA3 are stable in alkali, unlike their parent lactones GA1 and GA3. Both derivatives are biologically active in inducing alpha-amylase production in protoplasts of Avena fatua aleurone. They have biological activities of one order of magnitude less than that of the natural analogues. These data reveal the significant contribution of the lactone carbonyl to the observed response (receptor affinity) of GA1 and GA3.

  DOI：

  10.1016/0031-9422(91)80004-k