1'-hydroxy-α-ionone | 38736-62-8

• 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: 1'-hydroxy-α-ionone
• 英文别名: (E)-4-(1-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one
• CAS: 38736-62-8
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: LUIHIYPHXZXPRG-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1'-hydroxy-α-ionone 在 氢氧化钾 作用下， 以 乙醇 、 xylene 为溶剂， 反应 14.0h， 生成 1'-OH-α-ionylideneacetic acid
  参考文献：
  名称：

  松果尾孢菌中α-亚亚乙基乙醇生物合成脱落酸

  摘要：

  摘要 - 2 H-标记的 α-亚亚乙基乙醇被 Cercospora pini-densiflorae 通过 (1'R)-4' S-羟基-α-亚亚乙基乙酸有效地结合到 ABA 的 1',4'- 反式二醇中，和 2 H-标记的α-亚亚乙基乙酸通过(1' R )-4' R -羟基-α-亚亚乙基乙酸结合到1'-脱氧ABA中。这些和其他推定中间体的进料结果表明，在这种真菌中，ABA 是从 α-亚亚乙基乙醇通过 (1' R )-4' S -羟基-α-亚亚基乙酸到 1',4'- 反式- ABA的二醇，因此是ABA。

  DOI：

  10.1016/0031-9422(88)80749-0
• 作为产物：
  描述：

  beta-紫罗酮 在 正丁基锂 、 二乙胺 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 1'-hydroxy-α-ionone
  参考文献：
  名称：

  2-Fluoroabscisic Acid Analogues:  Their Synthesis and Biological Activities

  摘要：

  Fluorine was introduced into the 2-position of the side chain of abscisic acid (ABA) analogues by Wittig reaction of alpha-ionone derivatives with ethyl triethylphosphono-2-fluoroacetate. The effects of the fluorinated analogues were evaluated on inhibition of cr ess seed germination and inhibition of gibberellin-inducible alpha-amylase induction in embryoless barley half-seeds. (2E,4E)-2-Fluoro-5-(1'-hydroxy-2',6', ,6'-trimethyl-2'-cyclohexen-1'-yl)-3-methyl-2,4-pentadienoic acid (5b) showed potent inhibitory activity at the same level as ABA in the cress seed germination test, and 5b also inhibited gibberellin-inducible alpha-amylase induction at 4 x 10(-6), 3 times the concentration of ABA (1 x 10(-6)) for 50% inhibition of alpha-amylase production. 5b also showed dehydrin induction activity. These results indicate that fluorinated ABA analogues mimic ABA action and can be a lead for a plant growth regulator which regulates plant growth or protects plants from environmental stresses.

  DOI：

  10.1021/jf980265l

文献信息

• Stereochemical studies. XXXIX. A novel method for the preparation of optically active aldehydes. Syntheses of optically active (R)(+)-.ALPHA.-cyclo+)-.ALPHA.-l, (S) (+)-dehydrovomifoliol, and (S) (+)-abscisic acid.
  作者：MASAKATSU SHIBASAKI、SHIRO TERASHIMA、SHUNICHI YAMADA

  DOI：10.1248/cpb.24.315

  日期：——

  It was found that direct hydrolysis of the crude oxazolidine derivatives (3a, b), prepared with dl-α-cyclocitral (dl-1a), or its 6-benzoxy derivative (dl-1b) and (S) (+)-prolinol ((S) (+)-4), with aqueous acetic acid, afforded (R) (+)-1a, 19% optically pure, and (S) (+)-6-hydroxy-α-cyclocitral ((S) (+)-2b), 63% optically pure, respectively. A merit of the resolution method is that optically active (R) (+)-1a or (S) (+)-2b can be obtained without any recrystallizations. Some mechanistic studies and discussions on the hydrolysis were also examined. Optically active (S) (+)-2b, thus obtained, was successfully converted into (S) (+)-dehydrovomifoliol ((S) (+)-5) via (S) (+)-6-hydroxy-α-ionone ((S) (+)-9). By this chemical conversion, (S) (+)-abscisic acid could be formally synthesized from dl-1b.

  发现用dl-α-环柠檬醛(dl-1a)或其6-苯氧基衍生物(dl-1b)和(S)(+)-脯氨醇直接水解粗恶唑烷衍生物(3a,b) ((S)(+)-4)与乙酸水溶液反应，得到(R)(+)-1a，19%光学纯，和(S)(+)-6-羟基-α-环柠檬醛((S) (+)-2b)，光学纯分别为 63%。拆分方法的优点是无需任何重结晶即可获得光学活性的(R)(+)-1a或(S)(+)-2b。还检查了一些关于水解的机理研究和讨论。由此获得的光学活性(S)(+)-2b，通过(S)(+)-6-羟基-α-成功转化为(S)(+)-脱氢伏米叶醇((S)(+)-5)紫罗兰酮 ((S) (+)-9)。通过这种化学转化，可以从dl-1b正式合成(S)(+)-脱落酸。
• Norman, Shirley M.; Poling, Stephen M.; Maier, V. P., Agricultural and Biological Chemistry, 1985, vol. 49, # 8, p. 2317 - 2324
  作者：Norman, Shirley M.、Poling, Stephen M.、Maier, V. P.、Nelson, Mary D.

  DOI：——

  日期：——
• The metabolism of α-ionylidene compounds by Cercospora rosicola☆
  作者：Steven J. Neill、Roger Horgan、Daniel C. Walton、Carola A.M. Mercer

  DOI：10.1016/s0031-9422(00)83867-4

  日期：——
• OKAMOTO, MASAHIKO;HIRAI, NOBUHIRO;KOSHIMIZU, KOICHI, PHYTOCHEMISTRY, 27,(1988) N 11, C. 3465-3469
  作者：OKAMOTO, MASAHIKO、HIRAI, NOBUHIRO、KOSHIMIZU, KOICHI

  DOI：——

  日期：——