(2E,4E)-ethyl 2-fluoro-3-methyl-5-(4'-oxo-2',6',6'-trimethyl-2'-cyclohexen-1'-yl)-2,4-pentadienoate | 219972-53-9

• 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: (2E,4E)-ethyl 2-fluoro-3-methyl-5-(4'-oxo-2',6',6'-trimethyl-2'-cyclohexen-1'-yl)-2,4-pentadienoate
• 英文别名: ethyl (2E,4E)-2-fluoro-3-methyl-5-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)penta-2,4-dienoate
• CAS: 219972-53-9
• 化学式: C₁₇H₂₃FO₃
• 分子量: 294.366
• InChiKey: UHYHCJLPRGEFPI-XHBXSBNISA-N

物化性质

• 沸点：
  390.925±42.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.077±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E,4E)-ethyl 2-fluoro-3-methyl-5-(4'-oxo-2',6',6'-trimethyl-2'-cyclohexen-1'-yl)-2,4-pentadienoate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以81%的产率得到(2E,4E)-2-fluoro-3-methyl-5-(4'-oxo-2',6',6'-trimethyl-2'-cyclohexen-1'-yl)-2,4-pentadienoic acid
  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
• 作为产物：
  描述：

  alpha-ionone 、 alkaline earth salt of/the/ methylsulfuric acid 在 jones reagent 、 sodium hydride 作用下， 以 丙酮 为溶剂， 反应 23.0h， 生成 (2E,4E)-ethyl 2-fluoro-3-methyl-5-(4'-oxo-2',6',6'-trimethyl-2'-cyclohexen-1'-yl)-2,4-pentadienoate
  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

• 2-Fluoroabscisic Acid Analogues:  Their Synthesis and Biological Activities
  作者：Bum Tae Kim、Yong Ki Min、Tadao Asami、No Kyun Park、Oh Young Kwon、Kwang Yun Cho、Shigeo Yoshida

  DOI：10.1021/jf980265l

  日期：1999.1.1

  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.