ent-3α-acetoxy-2α-chloro-13-hydroxy-20-norgibberell-16-en-19-oic acid 19,10-lactone | 522654-08-6

• 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: ent-3α-acetoxy-2α-chloro-13-hydroxy-20-norgibberell-16-en-19-oic acid 19,10-lactone
• CAS: 522654-08-6
• 化学式: C₂₁H₂₅ClO₇
• 分子量: 424.878
• InChiKey: URBDJVRPPOYARA-BXHIQJQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  29.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  110.13
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ent-3α-acetoxy-2α-chloro-13-hydroxy-20-norgibberell-16-en-19-oic acid 19,10-lactone 在 氢氧化钾 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 以81%的产率得到(1R,2R,5S,8S,9S,10R,11S,12R,14S)-5-羟基-11-甲基-6-亚甲基-17-氧代-13,16-二氧杂六环[9.4.2.1(5,8).0(1,10).0(2,8).0(12,14)]十八烷-9-羧酸
  参考文献：
  名称：

  Synthesis of gibberellin GA6 and its role in flowering of Lolium temulentum

  摘要：

  The induction of flowering by one long day (LD) in the grass Lolium temulentum is most closely mimicked by application of the gibberellins (GAs) GA(5) or GA(6), both of which occur naturally. These gibberellins promote floral development but have little effect on stem elongation. Endogenous GA(5) and GA(6) contents in the shoot apex double on the day after the LD and, for GA(5) (and we presume for GA(6) as well) reach a concentration known to be inductive for the excised shoot apex in vitro. They are, therefore, strong candidates as LD floral stimuli in this grass. The synthesis of GA(6) and an examination of its florigenic properties in L. temulentum are described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(02)00447-8
• 作为产物：
  描述：

  赤霉素 A5 在 四氧化锇 、 对甲苯磺酸 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 丙酮 、 乙腈 、 叔丁醇 为溶剂， 反应 2.75h， 生成 ent-3α-acetoxy-2α-chloro-13-hydroxy-20-norgibberell-16-en-19-oic acid 19,10-lactone
  参考文献：
  名称：

  Synthesis of gibberellin GA6 and its role in flowering of Lolium temulentum

  摘要：

  The induction of flowering by one long day (LD) in the grass Lolium temulentum is most closely mimicked by application of the gibberellins (GAs) GA(5) or GA(6), both of which occur naturally. These gibberellins promote floral development but have little effect on stem elongation. Endogenous GA(5) and GA(6) contents in the shoot apex double on the day after the LD and, for GA(5) (and we presume for GA(6) as well) reach a concentration known to be inductive for the excised shoot apex in vitro. They are, therefore, strong candidates as LD floral stimuli in this grass. The synthesis of GA(6) and an examination of its florigenic properties in L. temulentum are described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(02)00447-8