A 1-iodo-3-perfluoroalkyl olefin compound and its preparation method

A technology of perfluoroalkyl olefins and perfluoroalkyl iodides, applied in the field of 1-iodo-3-perfluoroalkyl olefin compounds and their preparation, to achieve high yield, high cis-trans selectivity, and rich reactivity Effect

Active Publication Date: 2021-11-05
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] But, in the synthetic method of existing alkenyl iodide, generally need to introduce initiator and additive, as Chinese patent CN106832256A discloses adopting perfluoroalkyl iodide R f -I reacts with vinyl or propylene-containing polyoxyethylene ether to obtain a fluorine-containing nonionic surfactant. In the preparation process, the initiator is added twice, and there are certain limitations in the application process.

Method used

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  • A 1-iodo-3-perfluoroalkyl olefin compound and its preparation method
  • A 1-iodo-3-perfluoroalkyl olefin compound and its preparation method
  • A 1-iodo-3-perfluoroalkyl olefin compound and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1 (Z)-5,5,5-trifluoro-2-iodopent-2-enoic acid butyl ester

[0050]

[0051] Add 0.4mmol n-butyl alkenyldiazoacetate, an appropriate amount of acetonitrile and 0.8mmol trifluoroiodomethane into a Schlenk bottle, and react under 18W CFL light irradiation for 1h at room temperature. Subsequently, the reaction solution was concentrated to remove excess trifluoroiodomethane, and then an appropriate amount of acetonitrile and 0.06 mmol of dimanganese decacarbonyl catalyst were added to the reaction test tube. After continuing to react for 9 hours under the same light source, the reaction solution was concentrated, petroleum ether / Ethyl acetate = 50:1 mixed solvent as eluent column chromatography purification to obtain (Z)-5,5,5-trifluoro-2-iodopent-2-enoic acid butyl ester with a yield of 85% , Z / E>30:1. Its structure is as follows:

[0052]

[0053] The NMR and high-resolution data of the compound are as follows:

[0054] 1 H NMR (400MHz, CDCl 3 )δ7.26(t,...

Embodiment 2

[0058] Example 2 (Z)-5,5,6,6,7,7-heptafluoro-2-iodohept-2-enoic acid butyl ester

[0059]

[0060] Add 0.4mmol n-butyl alkenyl diazoacetate, an appropriate amount of acetonitrile and 1.6mmol perfluoroiodopropane into a Schlenk bottle, and react under sunlight irradiation for 5h at room temperature. Subsequently, the reaction solution was concentrated to remove excess heptafluoroiodopropane, and then an appropriate amount of acetonitrile and 0.01 mmol of dimanganese decacarbonyl catalyst were added to the reaction test tube, and the reaction was continued for 1 h under the same light source, and the reaction solution was concentrated, petroleum ether / Ethyl acetate = 50:1 mixed solvent as eluent column chromatography to obtain (Z)-5,5,6,6,7,7-heptafluoro-2-iodohept-2-enoic acid butyl ester , the yield is 86%, Z / E>30:1. Its structure is as follows:

[0061]

[0062] The NMR and high-resolution data of the compound are as follows:

[0063] 1 H NMR (400MHz, CDCl 3 )δ7.3...

Embodiment 3

[0067] Example 3 (Z)-5,5,6,6,7,7,8,8,8-nonafluoro-2-iodo-2-enoic acid butyl ester

[0068]

[0069] Add 0.4 mmol n-butyl alkenyl diazoacetate, an appropriate amount of dichloromethane and 2.0 mmol nonafluoro-n-butyl iodide into a Schlenk bottle, and react under 5W LED white light irradiation for 10 h at room temperature. Subsequently, the reaction solution was concentrated to remove excess nonafluoro-n-butyl iodide, and then an appropriate amount of dichloromethane and 0.15 mmol of dimanganese decacarbonyl catalyst were added to the reaction test tube, and the reaction was continued for 12 hours under the same light source, and the reaction solution was concentrated , petroleum ether / ethyl acetate=50:1 mixed solvent as the eluent column chromatography to obtain (Z)-5,5,6,6,7,7,8,8,8-nonafluoro-2 - Iodo-2-enoic acid butyl ester, the yield is 85%, Z / E>30:1. Its structure is as follows:

[0070]

[0071] The NMR and high-resolution data of the compound are as follows:

...

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PUM

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Abstract

The invention discloses a 1-iodine-3-perfluoroalkyl olefin compound and a preparation method thereof. The compound of the present invention has a structure as shown in formula (I), and this 1-iodine-3-perfluoroalkyl olefin compound can be widely used in coupling reactions or free radical rings because of its high chemical activity and rich reactivity. Addition reaction. The preparation method of the present invention has a wide range of substrate adaptability, and can synthesize a variety of 1-iodine-3-perfluoroalkyl olefin compounds; and the raw materials are cheap and easy to obtain, and the by-product is only nitrogen, which conforms to the concept of green synthesis and the operation of the reaction process Simple, insensitive to air and moisture, high yield, simple product separation and purification, high cis-trans selectivity of alkenyl iodide, suitable for large-scale synthesis, and has good application prospects.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to 1-iodo-3-perfluoroalkyl olefin compounds and a preparation method thereof. Background technique [0002] The fluorine atom has a high electronegativity, which greatly affects the electron cloud distribution, acidity and alkalinity, and dipole moment of the fluorine-containing compound, making the physical and chemical properties of the fluorine-containing compound significantly changed. Since the last century, many fluorine-containing organic compounds have been gradually used in medicines and materials. Therefore, scientists have carried out a lot of research to find new ways to introduce fluorine atoms or fluorine-containing functional groups into organic molecules, among which the new method of introducing perfluoroalkyl groups, especially trifluoromethyl groups, has attracted special attention. In the past decade, great progress has been made in the visi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/343C07C67/333C07C69/65C07C315/04C07C317/44C07C69/738C07D311/72C07D493/04C07J9/00C07D211/34
CPCC07B2200/09C07C67/333C07C67/343C07C69/65C07C69/738C07C315/04C07C317/44C07D211/34C07D311/72C07D493/04C07J9/00C07C2601/14C07C2603/74
Inventor 周磊李伟宇
Owner SUN YAT SEN UNIV
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