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Method for synthesizing 2, 3, 5 (Z)-trienol containing fluorine

A technology of trienol and addition, applied in chemical instruments and methods, preparation of organic compounds, preparation of hydroxyl compounds, etc., can solve problems such as limitation and achieve the effect of high reaction yield

Inactive Publication Date: 2009-09-02
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, reports on the synthesis of fluorine-containing allenes are still relatively limited.

Method used

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  • Method for synthesizing 2, 3, 5 (Z)-trienol containing fluorine
  • Method for synthesizing 2, 3, 5 (Z)-trienol containing fluorine
  • Method for synthesizing 2, 3, 5 (Z)-trienol containing fluorine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Take a reaction tube, bake it under vacuum, fill it with nitrogen to remove moisture, dry it thoroughly three times, and then cool it to room temperature under nitrogen atmosphere. Add 6,6,7,7,8,8,9,9,9-nonafluoro-4-butyl-4(E)-nonen-2-yn-1-ol (E-18b) into the reaction tube (70.0 mg, 0.197 mmol) and 0.5 mL of anhydrous ether. At room temperature, 0.48 mL of a tetrahydrofuran solution (1.73 M) of phenylmagnesium chloride was added dropwise into the reaction tube with a syringe, and the dropwise addition was completed within 2 minutes, and the reaction was continued for 2 hours at room temperature. Then put the reaction tube into an ice-water bath, and slowly add 5 mL of saturated NH 4 Quenched with Cl solution, extracted with ether (25mL×3), combined the organic phases, washed with saturated NaCl solution (10mL×2), anhydrous NaCl 2 SO 4 After dry filtration, concentration, and flash column chromatography, 75.5 mg of the product was obtained with a yield of 95%. The pr...

Embodiment 2

[0022] According to the method described in Example 1, the difference is that the substrates and reagents used are: 6,6,7,7,8,8,9,9,9-nonafluoro-4-butyl-4(E)- Nonen-2-yn-1-ol (318.9mg, 1.25mmol) and 4-methoxyphenylmagnesium bromide (2.0M in THF, 0.40mL, 0.80mmol) were dissolved in 0.5mL anhydrous diethyl ether at room temperature Under the solvent, reacted for 2 hours to obtain 83.0 mg of the product, and the yield was 93%. The product is a yellow liquid.

[0023]

[0024] 1 HNMR (300MHz, CDCl 3 )δ 7.35-7.27(m, 2H), 6.94-6.87(m, 2H), 5.92(d, J=34.2Hz, 1H), 4.57(s, 2H), 3.81(s, 3H), 2.38(t, J=7.4Hz, 2H), 1.69(bs, 1H), 1.55-1.30(m, 4H), 0.90(t, J=7.2Hz, 3H); 19 F NMR (282MHz, CDCl 3 )δ-80.8-(-80.9)(m, 3F), -118.0-(-118.2)(m, 2F), -127.2-(-127.6)(m, 3F); 13 C NMR (75MHz, CDCl 3 )δ 207.1 (d, J=4.4Hz), 159.2, 144.7 (dt, J 1 =267.8Hz and J 2 =27.8Hz), 127.6, 125.5, 114.2, 112.3-112.0(m), 108.0, 103.4(d, J=3.2Hz), 61.9, 55.3, 31.8(d, J=2.8Hz), 30.4, 22.2, 13.8; IR(neat)v...

Embodiment 3

[0026] According to the method described in Example 1, the difference is that the substrates and reagents used are: 6,6,7,7,8,8,9,9,9-nonafluoro-4-butyl-4(E)- Nonen-2-yn-1-ol and 4-fluorophenylmagnesium bromide (2.0M in THF, 0.40mL, 0.80mmol) were reacted for 2 hours at room temperature in 0.5mL of anhydrous ether as a solvent to obtain the product 78.6 mg, 89% yield. The product is a yellow liquid.

[0027]

[0028] 1 HNMR (300MHz, CDCl 3)δ 7.41-7.31(m, 2H), 7.11-7.00(m, 2H), 5.91(d, J=34.2Hz, 1H), 4.58(s, 2H), 2.38(t, J=74Hz, 2H), 1.72(bs, 1H), 1.54-1.30(m, 4H), 0.90(t, J=72Hz, 3H); 19 F NMR (282MHz, CDCl 3 )δ-80.8-(-80.9)(m, 3F), -114.1-(-114.3)(m, 1F), -118.0-(-118.2)(m, 2F), -126.3-(-126.7)(m , 1F), -127.2-(-127.4)(m, 2F); 13 C NMR (75MHz, CDCl 3 )δ 207.2 (d, J = 3.8Hz), 162.3 (d, J = 246.5), 145.0 (dt, J 1 =266.5Hz and J 2 =27.8Hz), 129.4(d, J=3.5Hz), 128.1(d, J=7.6Hz), 115.7(d, J=22.1Hz), 111.9-111.6(m), 107.5, 103.3(d, J= 3.2Hz), 61.9, 31.8(d, J=2.9Hz), 3...

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Abstract

The invention relates to a method for synthesizing 2, 3, 5 (Z)-trienol containing fluorine in a high-zone and stereoselectivity way, i.e. 2, 3, 5 (Z)-trienol compound containing fluorine is synthesized through the addition-elimination reaction of Grignard reagent and 5-perfluoroalkyl-4(E)-olefin-2-alkyne-1-alcohol. The method is simple to operate and easy to obtain raw materials and reagent; the reaction has high-zone and stereoselectivity without participation of noble metal, can simultaneously introduce a plurality of substitutional groups, has high yield and easy separation and purification of the product, and is suitable for synthesizing various 2, 3, 5 (Z)-trienols containing fluorine.

Description

technical field [0001] The present invention relates to a method for synthesizing fluorine-containing 2,3,5(Z)-trienol with high regioselectivity and stereoselectivity, that is, by Grignard reagent and 5-perfluoroalkyl-4(E)-ene- Synthesis of fluorinated 2,3,5(Z)-trienols by addition-elimination reaction of 2-yn-1-ols. Background technique [0002] Allenes have multifunctional loading properties and rich reactivity, and the introduction of fluorine atoms into molecules can bring many unique properties to organic compounds. In modern medicine and agricultural chemistry, the introduction of fluorine atoms to change and improve the biological activity of compounds has become a hot spot in the research and development of new products. Therefore, the synthesis of fluorine-containing allenes has great development and utilization value in the fields of biotechnology, medicine and pesticides. However, reports on the synthesis of fluorine-containing allenes are still relatively limi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C33/48C07C29/44C07C43/23C07C41/30C07C33/42
Inventor 麻生明马志超曾荣
Owner ZHEJIANG UNIV
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