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Gamma-crotonic lactone with substituted aryl group in its 4th place and its solid phase synthesis process

A solid-phase synthesis method and a technology of butenolide, which is applied in the field of five-membered ring unsaturated lactone and its synthesis, can solve the problems of unsatisfactory yield and time-consuming, and achieve easy automation, low cost and good application prospects Effect

Inactive Publication Date: 2002-05-22
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Not to mention that some of the above methods use expensive reagents, some give unsatisfactory yields, even though they may be effective for the synthesis of one or several compounds, but it is necessary to quickly and easily obtain a large number of different compounds with the parent structure , but it is time-consuming and almost impossible

Method used

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  • Gamma-crotonic lactone with substituted aryl group in its 4th place and its solid phase synthesis process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 1.851 grams of functionalized polystyrene resin (theoretical maximum loading capacity 2.5 meq / g) was added to 55 milliliters of THF, under stirring at room temperature, 2.206 grams of p-iodobenzyl alcohol and 0.330 grams of sodium hydride were added successively, and the mixture was stirred Reflux for three days. Then cooled to room temperature, filtered, followed by DMF (10 ml × 3), DMF / H 2 O (10ml×3), H 2 The resin was washed with O (10 mL×3), DMF (10 mL×2), MeOH (20 mL×3), and dried in vacuo overnight to obtain 2.590 g of p-iodobenzyl ether supported on the resin.

[0027] 246 mg of the resin prepared by the above steps (theoretical maximum loading capacity 1.674 meq / g) was added to 2 ml of anhydrous acetonitrile, and 292 mg of 2,3-alkenedecanoic acid, diiso 0.56 ml of propylethylamine, 70 mg of tetrakis(triphenylphosphine) palladium and another 2 ml of anhydrous acetonitrile were reacted at 70°C for three days. Then cooled to room temperature, filtered, followed ...

Embodiment 2

[0030] 1.007 grams of functionalized polystyrene resin (theoretical maximum loading capacity 2.5 millieq / g) was added to 30 milliliters of THF, under stirring at room temperature, 1.200 grams of o-iodobenzyl alcohol and 0.180 grams of sodium hydride were added successively, and the mixture was stirred Reflux for three days. Then cooled to room temperature, filtered, followed by DMF (10 ml × 3), DMF / H 2 O (10ml×3), H 2 The resin was washed with O (10 mL×3), DMF (10 mL×2), MeOH (20 mL×3), and dried in vacuo overnight to obtain 1.385 g of o-iodobenzyl ether supported on the resin.

[0031] 93 mg of the resin (theoretical maximum loading 1.674 meq / g) prepared by the above steps was added to 2 ml of anhydrous acetonitrile, and 83 mg of 2,3-linked diene octanoic acid, diisopropyl 0.21 ml of ethyl ethylamine, 26 mg of tetrakis(triphenylphosphine) palladium and another 2 ml of anhydrous acetonitrile were reacted at 70° C. for three days. Then cooled to room temperature, filtered, f...

Embodiment 3

[0034] 92 mg of p-iodobenzyl ether loaded on the resin of Example 1 was added to 2 ml of anhydrous acetonitrile, and 84 mg of 2,3-diene octanoic acid and 0.21 ml of diisopropylethylamine were added successively under the protection of argon. React with 26 mg of tetrakis(triphenylphosphine) palladium and another 2 ml of anhydrous acetonitrile at 70° C. for three days. Then cooled to room temperature, filtered, followed by DMF (5 ml × 3), DMF / H 2 O (5ml×3), H 2 The resin was washed with O (5 mL×3), DMF (5 mL×2), MeOH (10 mL×3), and dried in vacuo overnight to obtain 99 mg of γ-butenolide loaded on the resin.

[0035] To a solution of 95 mg of the resin prepared above in dichloromethane (4 mL), add ZnBr 2 (24 mg) and bromoacetyl (0.33 ml). It was then stirred at room temperature for 24 hours and filtered. The filtrate was transferred to a separatory funnel, washed successively with 5% sodium bicarbonate solution, 5% hydrochloric acid solution and saturated brine, dried, and c...

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Abstract

The present invention relates to a gamma-butenolide whose four positions contain aryl substituent and its solid phase synthesis method. Said invention provides the structure formula of said compound.

Description

technical field [0001] The invention relates to a five-membered ring unsaturated lactone containing an aryl substituent at the 4-position and a synthesis method thereof, that is, gamma-butenoic acid lactone and a solid-phase synthesis method thereof. Background technique [0002] The five-membered unsaturated lactone ring is one of the most common structural components in natural products and has a variety of important physiological activities. For example, antibacterial and anti-inflammatory, antifungal, antitumor, and regulating seed germination and plant growth, etc., have great development and utilization value in medicine and pesticides. For a long time, people have been imagining how to establish a molecular library of such compounds, so as to systematically screen for biological activity. However, γ-butenolides containing aryl substituents at the 4-position have unique physiological activities. How to synthesize such compounds easily and efficiently? The traditional...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/33
Inventor 麻生明段德慧王意中
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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