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Isotopically labeled methyl furanone, intermediate and preparation method of isotopically labeled methyl furanone

An isotope labeling, methyl furanone technology, applied in the production of bulk chemicals, organic chemistry, etc., can solve the problems of harsh synthesis conditions, poor stability, low deuterium abundance of strigolactone, etc.

Inactive Publication Date: 2015-04-29
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is to overcome the shortcomings of isotope-labeled strigolactone deuterium abundance, poor stability, poor accuracy of plant hormone analysis and determination, low yield and harsh synthesis conditions in the prior art, and provide A kind of isotope-labeled methyl furanone, intermediate and preparation method thereof

Method used

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  • Isotopically labeled methyl furanone, intermediate and preparation method of isotopically labeled methyl furanone
  • Isotopically labeled methyl furanone, intermediate and preparation method of isotopically labeled methyl furanone
  • Isotopically labeled methyl furanone, intermediate and preparation method of isotopically labeled methyl furanone

Examples

Experimental program
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Effect test

Embodiment 1

[0099] Example 1 Synthesis of 3-bromofuran-2[5H]-one (compound 2) (according to literature Boukouvalas, J.; Loach, R.P. General, Regiodefined Access to α-Substituted Butenolidesthrough Metal-Halogen Exchange of 3-Bromo-2- Silyloxyfurans. Efficient Synthesis of an Anti-Inflammatory Gorgonian Lipid. J. Org. Chem. 2008, 73, 8109–8112. Reported method synthesis)

[0100]

[0101] Build the experimental device: 100mL three-neck flask, reflux condenser, constant pressure dropping funnel and thermometer, under nitrogen protection, add 3.13g (37.3mmol) furanone and 40mL anhydrous ether, and use an ice bath to lower the system temperature to 0°C. Then, 2.2 mL (43.4 mmol) of bromine and 10 mL of anhydrous ether were added to the dropping funnel, and the above solution was slowly added dropwise to the reaction system, and the dropwise addition was completed in 25 minutes. After dripping, reflux (about 35°C) to react for 4h. Then nitrogen gas was blown into the system for 1 hour to re...

Embodiment 2

[0102]Example 2 Synthesis of 2-triisopropylsilyloxy-3-bromofuran-2[5H]-one (compound 3) (according to literature Boukouvalas, J.; Loach, R.P.General, Regiodefined Access to α-Substituted Butenolides through Metal-Halogen Exchange of 3-Bromo-2-Silyloxyfurans. Efficient Synthesis of an Anti-Inflammatory Gorgonian Lipid. J. Org. Chem. 2008, 73, 8109–8112. Reported method synthesis)

[0103]

[0104] Add 0.503g (3.1mmol) 3-bromofuran-2[5H]-one and 20mL of dried dichloromethane into the Schlenk tube that has been replaced with nitrogen, cool the temperature to below 0°C in an ice-salt bath, and measure 0.56mL ( 4mmol) triethylamine, added dropwise in the reaction tube and finished dripping in 10 minutes, the reaction solution immediately turned dark brown from light yellow, added dropwise 1.242g (4mmol) triisopropylmethyl trifluoromethanesulfonate, and reacted Liquor turns orange-red immediately, then gradually turns into wine red, keeps stirring in ice-salt bath for 30min after...

Embodiment 3

[0105] Example 3 CD 3 -Synthesis of iodomethane (Compound 5A)

[0106]

[0107] Add 5mL deuterated methanol, 5mL water and 50mL hydroiodic acid (mass percentage is 55.0%-58.0%) in reaction flask, and described mass percentage refers to the percentage that the quality of hydrogen iodide accounts for hydroiodic acid gross mass; Phosphoric acid stabilizer mass percentage is 1.5%, and described mass percentage refers to the mass percentage of hypophosphorous acid stabilizer accounted for hydroiodic acid reagent gross mass), stirs, is heated to 40 ℃ of reaction 2h, is heated to 50 ℃ of reaction 2h, drops After reaching room temperature (about 20°C), replace it with a distillation apparatus, collect fractions at 40°C to 45°C under normal pressure (1 atm), and distill at a rate of 0.1mL / s to obtain 13.25g of a colorless liquid with a yield of 83.8%.

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Abstract

The invention discloses isotopically labeled methyl furanone, an intermediate and a preparation method of isotopically labeled methyl furanone. The invention provides isotopically labeled methyl furanone 6. The invention further provides a preparation method of isotopically labeled methyl furanone 6, and the preparation method comprises the following steps: performing removal of a hydroxy protecting group and isomerization reaction on a compound 20 in the presence of an acid. The method provided by the invention comprises short reaction steps, labeling loci are stable, are labeled on a common D ring of a strigolactone type compound family and are successfully butted with ABC rings of strigolactone type compounds to obtain a variety of isotopically labeled strigolactone type compounds with different isotopic abundances which are more than 99% respectively, and the isotopically labeled methyl furanone is applicable to wide substances, is used as an internal source standard matter for GC-MS and LC-MS / MS analysis and has high detection sensitivity and good accuracy, thereby having broad market application prospects.

Description

technical field [0001] The invention specifically relates to isotope-labeled methyl furanone, an intermediate and a preparation method thereof. Background technique [0002] Strigolactones (SLs) are a general term for some natural strigal compounds and synthetic analogues, which were discovered from the research on germination stimulants of parasitic plants. The strigolactones (SLs) found naturally in plants have always been regarded as important signaling molecules. When nutrients such as phosphorus in the soil are deficient, the SLs secreted by the plant rhizosphere as signal molecules can also be stimulated by the rhizosphere microbiota. Mycelium formation and spore germination of AM fungi can be recognized by AM, thereby helping plants to absorb nutrients such as phosphorus in the soil. In addition, as a new class of plant hormones, strigolactone inhibits the growth of branches and lateral buds of plants, maintains the plant shape of plants together with auxin and cytok...

Claims

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Application Information

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IPC IPC(8): C07D307/58C07D307/93
CPCY02P20/55C07D307/58C07D307/93
Inventor 丁文慧龙沁李晓强方童杨军
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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