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Polysubstituted alpha-alkenyl lactone compound and preparation method and application thereof

An alkenyl lactone, multi-substituted technology, applied in the directions of organic chemistry, drug combination, anti-infective drugs, etc., can solve the problems of many reaction steps, low yield, etc., and achieves low cost, good yield, and good application prospects. Effect

Pending Publication Date: 2021-01-12
CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although there are many methods for synthesizing α-alkenyl lactones, these methods all have places that need to be improved. For example, there are problems such as the use of a strong base in the reaction, many reaction steps, and low yield. The synthesis of this type of molecule still faces huge challenges. challenge

Method used

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  • Polysubstituted alpha-alkenyl lactone compound and preparation method and application thereof
  • Polysubstituted alpha-alkenyl lactone compound and preparation method and application thereof
  • Polysubstituted alpha-alkenyl lactone compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Target compound:

[0039]

[0040] Preparation method: add 3.0g of phenylpropylic acid and 2.3g of ferric oxalate to the reaction bottle, add 7ml of acetonitrile and methanol mixed solvent, weigh 1.5g of 2-methallyl alcohol, 2.6g of triethylsilane, and react at room temperature After 8 hours, it was quenched by adding water, extracted with ethyl acetate, and recrystallized to obtain 3.4 g of white solid, with a yield of 82%.

[0041] Product characterization: white solid, melting point, 96-97°C, 1 H NMR (400MHz, CDCl3 ):δ7.67 (s,1H),7.43-7.32(m,5H),3.96(s,2H),1.28(s,6H). 13 C NMR (101MHz, CDCl 3 ): δ172.54, 138.14, 135.27, 134.18, 129.27, 128.86, 128.26, 78.96, 39.48, 25.70. HRMS (m / z): calcd for C 13 h 14 NaO 2 + [M + Na] + :225.0886,found: 225.0892.

Embodiment 2

[0043] Target compound:

[0044]

[0045] Preparation:

[0046] Preparation method: Add 3.6g of p-chlorobenzoic acid, 2.6g of nickel acetylacetonate in sequence, add 5ml of mixed solvent of ethanol and THF, weigh 2.8g of cyclohex-1-en-1-ylmethanol, 4.0g of benzene Silane was refluxed for 3 hours, quenched by adding water, extracted with ethyl acetate, and separated by column chromatography to obtain 4.1 g of white solid with a yield of 86%.

[0047] Product characterization: white solid, melting point, 124-125°C. 1 H NMR (400MHz, CDCl 3 ):δ 7.73(s,1H),7.47-7.33(m,5H),4.18(s,2H),1.82-1.75(m,2H),1.72-1.60(m, 5H),1.30-1.17(m, 2H),1.18-1.04(m,1H). 13 C NMR (101MHz, CDCl 3 ): δ 172.88, 138.66, 135.23, 134.40, 129.25, 128.87, 128.61, 128.22, 74.76, 43.61, 33.63, 24.90, 22.48. HRMS (m / z): calcd for C 16 h 18 o 2 [MH] + :243.13763,Found: 243.13763.

Embodiment 3

[0049] Target compound:

[0050]

[0051] Preparation:

[0052] R in the reactant 1 = phenyl, R 2 +R 3 = Cyclopentyl, R 4 , R 5 = hydrogen, n = 0; solvent is toluene, catalyst is FeCl 3 , the reducing agent is HSiCl 3 ; The molar ratio of reactants I and II is 1:0.3; the molar ratio of reactant I and catalyst is 1:0.05; the molar ratio of reactant I and reducing agent is 1:0.5. The reactant, solvent, catalyst and reducing agent were added into the reaction flask in sequence, refluxed for 2 hours, quenched with water, extracted with ethyl acetate, and separated by column chromatography to obtain a white solid with a yield of 80.2%.

[0053] Product characterization: white solid, melting point, 78-79°C. 1 H NMR (400MHz, CDCl 3 ):δ7.65 (s,1H),7.42-7.31(m,5H),4.00(s,2H),2.09-2.01(m,2H),1.82-1.72(m,2H), 1.70-1.59(m ,4H). 13 C NMR (101MHz, CDCl 3 ): δ173.02, 137.48, 134.13, 132.93, 129.58, 129.01, 128.82, 128.52, 128.30, 79.82, 50.19, 36.55, 25.33. HRMS (m / z): calcd f...

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Abstract

The invention belongs to the field of organic synthesis, and provides a polysubstituted alpha-alkenyl lactone compound, and a preparation method and application thereof, the structure of the polysubstituted alpha-alkenyl lactone compound is as follows that: R1 is selected from aryl or heteroaryl, R2 and R3 are respectively and independently selected from C1-C6 alkyl, R4 and R5 are each independently selected from an aryl group, and an aromatic heterogroup or a C1-C6 alkyl group. The polysubstituted alpha alkenyl lactone compound is obtained by reacting acetylenic acid with allyl alcohol or allyl butanol for 1-24 hours from room temperature to reflux temperature under the action of a catalyst and a hydrogen source. According to the method, the target product can be prepared through one-stepreaction, and the method is simple in synthesis method, simple in process equipment, easy to operate, environmentally friendly, low in cost and good in yield.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a multi-substituted α-alkenyl lactone compound, its preparation method and application. Background technique [0002] As shown below, the structural motif of α-alkenyl lactones has been found in a large number of synthetically challenging and biologically interesting natural products, many of which have promising biological activities (e.g., anticancer, antimalarial, antiviral , antibacterial, antifungal, anti-inflammatory, etc.). [0003] [0004] Natural products containing alpha-enyl lactone structures are especially important. Examples include acyanin, the anti-inflammatory active ingredient of honeysuckle, widely used in liniments and ointments to treat strains, sprains, and bruises; monophenolactone, a sesquiterpene isolated from the medicinal herb feverfew lactones, which have potent anti-inflammatory, anticancer and antiviral properties; histone alcohols (...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/58C07D307/94C07D407/04C07D307/93C07D309/32C07D407/06C07D409/06A61P35/00A61P33/06A61P31/12A61P31/04A61P31/10A61P29/00
CPCA61P29/00A61P31/04A61P31/10A61P31/12A61P33/06A61P35/00C07D307/58C07D307/93C07D307/94C07D309/32C07D407/04C07D407/06C07D409/06
Inventor 王继宇张华张远康张淑青
Owner CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI
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