赤霉素A5甲酯 | 15355-45-0

• 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
• 中文名称: 赤霉素A5甲酯
• 英文名称: gibberellin A₅ methyl ester
• 英文别名: GA₅ 7-methyl ester；4a,7-dihydroxy-1β-methyl-8-methylene-4aα,7β-gibb-2-ene-1α,10β-dicarboxylic acid-1=>4a lactone-10-methyl ester；4a,7-Dihydroxy-1β-methyl-8-methylen-4aα,7β-gibb-2-en-1α,10β-dicarbonsaeure-1=>4a-lacton-10-methylester；A5-Me；Gibberellin A5 methyl ester；methyl (1R,2R,5S,8S,9S,10R,11R)-5-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadec-12-ene-9-carboxylate
• CAS: 15355-45-0
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: KIAZKTCYLHEASA-HOWNIQBVSA-N

物化性质

• 沸点：
  514.5±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  赤霉素A5甲酯 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 赤霉素 A5
  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 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 24.25h， 生成 赤霉素A5甲酯
  参考文献：
  名称：

  Schneider, Gernot; Schmidt, Juergen, Liebigs Annalen der Chemie, 1994, # 11, p. 1149 - 1152

  摘要：

  DOI：

文献信息

• An efficient method for the reductive transposition of allylic alcohols
  作者：Andrew G Myers、Bin Zheng

  DOI：10.1016/0040-4039(96)00965-3

  日期：1996.7

  Mitsunobu reaction of allylic alcohols with o-nitrobenzenesulfonylhydrazine (NBSH) as nucleophile proceeds at −30 °C with invertive displacement; warming the resultant N-allylic sulfonylhydrazine derivative to 23 °C then leads to allylic diazene formation followed by sigmatropic elimination of dinitrogen. This one-step method for reductive 1,3-transposition is shown to be efficient and highly regio- and

  烯丙基醇与邻硝基苯磺酰基肼（NBSH）亲核试剂的Mitsunobu反应在−30°C下进行反相置换。将所得的N-烯丙基磺酰基肼衍生物加热至23℃，然后导致形成烯丙基二氮烯，然后通过σ消除二氮。这种用于还原性1,3-转移的一步方法显示出在多种烯丙醇底物内均有效且高度区域和立体受控的方法。
• Allylic chlorination of gibberellins A3 and A7 methyl esters and of gibberellin A3: preparation of gibberellin A5
  作者：John R. Bearder、Paul S. Kirkwood、Jake MacMillan

  DOI：10.1039/p19810000672

  日期：——

  methyl ester and of the isomeric 1(10)-ene-19,2-lactone. Hydrolysis of gibberellin A5 methyl ester 13-acetate gives gibberellin A5 in 20% overall yield from gibberellin A3. [1-2H1]Gibberellin A5 is obtained in the same way by using tri-n-butyl-[2H1]stannane in the reduction step. Analogous chlorination products of gibberellin A7 methyl ester and of gibberellin A3 are described.

  描述了赤霉素A 3向赤霉素A 5的高产率转化。与亚硫酰氯一起，赤霉素A 3甲酯主要得到1β-氯赤霉素A 5甲酯；异构体3α-氯-1-烯是与甲苯-对-磺酰氯和氯化锂反应的主要产物。将每种产物用三正丁基锡烷还原并乙酰化，得到赤霉素A 5甲酯的13-乙酸盐和异构体1（10）-烯-19,2-内酯的相同混合物。的赤霉素水解5甲基酯13乙酸酯给出赤霉素阿5从赤霉素A有20％总产率3。[1-通过在还原步骤中使用三正丁基-[ 2 H 1 ]锡烷以相同的方式获得2 H 1 ]赤霉素A 5。描述了赤霉素A 7甲酯和赤霉素A 3的类似氯化产物。
• Preparation and occurrence of gibberellins A75 and A76 and 3-epi-A72
  作者：Simon John Castellaro、Jake MacMillan、Arun Kumar Singh、Christine Louise Willis

  DOI：10.1039/p19900000145

  日期：——

  Three water-soluble compounds were detected in extracts from mature seeds of Helianthus annuus by g.l.c.–mass spectrometry. The structures of these putative gibberellins were confirmed by comparison with authentic samples of the 15β-hydroxygibberellins GA75, GA76, and 3-epi-GA72 prepared from GA3.

  通过glc-mass光谱法从向日葵成熟种子的提取物中检测到三种水溶性化合物。这些推定赤霉素的结构通过与15β-hydroxygibberellins GA的真实样品比较确认75，GA 76，和3-外延-GA 72从GA制备3。
• Preparation of gibberellins A9 and A20 from gibberellic acid
  作者：Zvitendo J. Duri、Braulio M. Fraga、James R. Hanson

  DOI：10.1039/p19810000161

  日期：——

  using triphenylphosphine and carbon tetrachloride. Hydrogenolysis of the chlorides with tributyltin hydride afforded gibberellins A20 and A9 as their methyl esters. Gibberellin A9 methyl ester was also prepared from the gibberellin A4/A7 mixture. The stereochemistry of the conjugate reduction of the ring-A-unsaturated ketone is defined.

  使用三苯膦和四氯化碳，赤霉酸甲酯已通过3-epigibberellin A 1的甲酯转化为3β-氯代和3β，13-二氯代衍生物。用氢化三丁基锡氢化氯化物，得到赤霉素A 20和A 9为它们的甲酯。赤霉素A 9甲酯也由赤霉素A 4 / A 7混合物制备。定义了环A-不饱和酮的共轭还原的立体化学。
• MacMillan et al., Proceedings of the Chemical Society, London, 1959, p. 325
  作者：MacMillan et al.

  DOI：——

  日期：——