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Synthesis method of 1-iodo-alkyne compound

A synthetic method and compound technology, applied in the preparation of organic compounds, silicon organic compounds, organic chemical methods, etc., to achieve the effects of easy products, wide adaptability of substrates, and simple reaction conditions

Active Publication Date: 2021-01-12
GUANGDONG UNIV OF PETROCHEMICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to overcome the defects and deficiencies of the existing alkyne iodide synthesis methods, and provide a new synthesis method of alkyne iodide compounds. The method has the advantages of simple reaction system, high selectivity, cheap and easy-to-obtain raw materials, green and environmentally friendly oxidant and The product is easy to separate and purify, etc.

Method used

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  • Synthesis method of 1-iodo-alkyne compound
  • Synthesis method of 1-iodo-alkyne compound
  • Synthesis method of 1-iodo-alkyne compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037]

[0038] Add 0.6mmol KI, 0.75mmol sodium p-toluene sulfinate, 4mL ethanol and 0.5mmol phenylacetylene to an ordinary test tube sequentially, open the test tube to the air, and stir the reaction at room temperature for about 12 hours. Followed by TLC to complete the reaction, separated by column chromatography to obtain a yellow oil, the eluent was sherwood oil / ethyl acetate (volume ratio of 50:1), the structure of the compound was obtained by NMR 1 H NMR, 13 C NMR and mass spectrometric tests. Yellow liquid, isolated yield 93%;

[0039] 1 H NMR (400MHz, CDCl 3 )δ7.44-7.42(m,2H),7.35-7.28(m,3H); 13 C NMR (100MHz, CDCl 3 )δ132.34,128.79,128.58,128.23,127.40,123.39,94.14,6.04; Ms(ESI):229[M+H] + .

Embodiment 2

[0041]

[0042] Add 0.6mmol KI, 0.75mmol sodium p-toluene sulfinate, 4mL ethanol and 0.5mmol p-toluene acetylene to an ordinary test tube in sequence, open the test tube to the air, and stir and react at room temperature for 12 hours. Followed by TLC to complete the reaction, separated by column chromatography to obtain a yellow oil, the eluent was sherwood oil / ethyl acetate (volume ratio of 50:1), the structure of the compound was obtained by NMR 1 H NMR, 13 C NMR and mass spectrometric tests. Yellow liquid, isolated yield 86%;

[0043] 1 H NMR (400MHz, CDCl 3 )δ7.32(d, J=8.1Hz, 2H), 7.11(d, J=7.9Hz, 2H), 2.35(s, 3H); 13 C NMR (100MHz, CDCl 3 )δ139.02, 132.20, 129.25, 128.98, 127.34, 120.37, 94.25, 21.52, 4.84; Ms(ESI):243[M+H] + .

Embodiment 3

[0045]

[0046] 0.6mmol KI, 0.75mmol sodium p-toluene sulfinate, 4mL ethanol and 0.5mmol p-ethylphenylacetylene were sequentially added into an ordinary test tube, and the test tube was exposed to the air, and stirred and reacted at room temperature for 12 hours. Followed by TLC to complete the reaction, separated by column chromatography to obtain a yellow oil, the eluent was sherwood oil / ethyl acetate (volume ratio of 50:1), the structure of the compound was obtained by NMR 1 H NMR, 13 C NMR and mass spectrometric tests. Yellow liquid, isolated yield 82%;

[0047] 1 H NMR (400MHz, CDCl 3)δ7.34(d, J=8.1Hz, 2H), 7.13(d, J=8.0Hz, 2H), 2.64(q, J=7.6Hz, 2H), 1.21(t, J=7.6Hz, 3H) ; 13 C NMR (100MHz, CDCl 3 )δ 145.29, 132.32, 132.31, 127.80, 120.61, 94.30, 28.85, 15.29, 4.90; Ms(ESI): 257[M+H] + .

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Abstract

The invention discloses a synthetic method of a 1-iodo-alkyne compound. The preparation method comprises the following steps: in an aerobic environment, mixing terminal alkyne, soluble inorganic iodized salt, sodium phenylsulfinate or a derivative thereof with an alcohol solvent, and reacting to obtain the 1-iodo-alkyne compound. According to the method, common iodide salt is used as an iodine source, and a high-valence iodine compound or elemental iodine does not need to be added; oxygen in the air is used as an oxidizing agent, and other oxidizing agents such as high-valence metals, high-valence iodine compounds, peroxides or persulfides do not need to be added; non-toxic or low-toxic alcohol is used as a solvent, and compared with an existing method, the solvent is more environmentallyfriendly; the synthesis method has the advantages that the reaction temperature is normal temperature, the reaction system does not need water-free or oxygen-free requirements, the reaction conditionsare simple, and the operation is easy; and the method disclosed by the invention has the advantages of wide substrate application, cheap and green raw materials, simple and mild reaction conditions,single product, easiness in purification and the like, and has extremely high economic value and application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 1-iodoalkyne compounds. Background technique [0002] Alkyne iodine compounds are widely distributed in natural medicines and synthetic medicines, and have some special biological and pharmaceutical activities. At the same time, alkyne iodine compounds are also an important class of organic synthesis intermediates, which can be used to construct carbon-carbon bonds, carbon-nitrogen bonds and carbon-oxygen bonds, and can be used for the efficient synthesis of drug molecules and conjugated optoelectronic materials. Therefore, the development of environmentally friendly and efficient synthetic methods of alkyne iodide will promote the theoretical research and practical application of such substances. The direct iodination of terminal alkynes to synthesize alkyne iodine compounds is the most direct method at present. These methods can be d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C17/14C07C22/04C07C22/08C07C41/22C07C43/225C07C25/24C07D213/26C07D333/12C07C29/62C07F7/08C07C33/42C07B39/00
CPCC07C17/14C07C41/22C07D213/26C07D333/12C07C29/62C07F7/083C07B39/00C07C22/04C07C22/08C07C43/225C07C25/24C07C33/426
Inventor 周鹏邱会华冯尚伟林白银刘卫兵张建涛
Owner GUANGDONG UNIV OF PETROCHEMICAL TECH
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