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Triallyloxydibenzo [b, f] oxepincycloacrylic compound, intermediate and application thereof

The technology of a compound, methoxybenzaldehyde, is applied in organic chemistry, bulk chemical production, etc. It can solve the problems of difficult separation and purification, low content, and limited applicability, and achieve fewer reaction steps, high yield, and easy operation. convenient effect

Active Publication Date: 2018-06-12
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the low content of salvianolic acid N in Danshen (extraction and separation yield was 8×10 -3 %, Journal of Asian Natural Products Research Vol.10, No.3, March 2008, 252–255), it is difficult to separate and purify it, which limits its applicability, so the development of new and efficient total synthesis of salvianolic acid N The method has important practical application value

Method used

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  • Triallyloxydibenzo [b, f] oxepincycloacrylic compound, intermediate and application thereof
  • Triallyloxydibenzo [b, f] oxepincycloacrylic compound, intermediate and application thereof
  • Triallyloxydibenzo [b, f] oxepincycloacrylic compound, intermediate and application thereof

Examples

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Effect test

Embodiment 1

[0040] Example 1: The preparation of 3-(3,4-diallyloxy)phenyl-2-hydroxy allyl propionate (9) was first based on the method reported in the literature (Tetrahedron, 2016, 72(33), 5047- 5050) to synthesize the compound 3-(3,4-diallyloxy)phenyl-2-hydroxy allyl propionate represented by formula (9).

Embodiment 2

[0041] Embodiment 2: the preparation of formula (2) compound

[0042] The compound of formula (1) (5.00g, 16.13mmol) and triphenylphosphine (4.23g, 16.13mmol) were dissolved in toluene (160mL), refluxed for 5h, cooled to room temperature, and suction filtered to obtain solid ylide salt. Then ylide salt and 5-bromo-2-hydroxy-3-methoxybenzaldehyde (4.95g, 16.13mmol) were dissolved in tetrahydrofuran (160mL), and 1,8-diazabicycloundeca-7 -alkene (2.45g, 16.13mmol), reflux reaction for 12h, the reaction solution was cooled to room temperature, extracted with ethyl acetate (200mL×3), the organic phases were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain The crude product was recrystallized to obtain the target compound 2 (6.45g), with a yield of 90%. 1 H NMR (500MHz, CDCl 3 ):δ7.05(s,1H,CH),6.90(d,J=2.1Hz,1H,CH),6.84(d,J=2.1Hz,1H,CH),6.77(s,1H,CH), 6.73(d,J=12.1Hz,1H,=CH),6.68(d,J=12.1Hz,1H,=CH),5.76(s,1H),3....

Embodiment 3

[0044] Change 1,8-diazabicycloundec-7-ene to butyllithium (10mL, 24.2mmol), change the amount of triphenylphosphine to (8.46g, 32.26mmol), 5-bromo-2 The amount of -hydroxyl-3-methoxybenzaldehyde was changed to (7.43g, 24.2mmol), the amount of solvent toluene was changed to (80mL), tetrahydrofuran (80mL), and other operations were the same as in Example 2 to obtain target compound 2 (5.38 g), the yield is 75%.

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Abstract

The invention provides a compound shown in a formula (7) and an intermediate (6) and also provides a new method for synthesizing a salvianolic-acid N compound shown in a formula (8). The new method comprises the following steps of: adopting a benzyl-bromide type compound as a raw material to react with 5-bromo-2-hydroxy-3-methoxybenzaldehyde by wittig to prepare a compound shown in a formula (2);then carrying out cyclization, Heck reaction and deprotection in sequence on the compound shown in the formula (2); then carrying out allyl protection, condensation with salvianic acid and deprotection to obtain the salvianolic-acid N compound shown in the formula (8). The new method provided by the invention has the advantages of fewer reaction steps, high yield, convenience in operation and mildreaction condition, and lays foundation for further application of salvianolic-acid N. (The formulas are described in the description).

Description

(1) Technical field [0001] The invention relates to an (E)-3-(4,7,8-triallyloxydibenzo[b,f]oxepin-2)-propenyl ester compound and its intermediate and its preparation Application of salvianolic acid N compounds. (2) Background technology [0002] Salvianolic acid N is one of the active ingredients of salvianolic acid, which has a variety of biological activities, such as anti-HIV and inhibition of α-glucosidase activity, can effectively fight diabetes and diabetic complications, and is effective in the treatment of AIDS and diabetes, etc. It has great application potential in diseases. Due to the low content of salvianolic acid N in Danshen (extraction and separation yield was 8×10 -3 %, Journal of Asian Natural Products Research Vol.10, No.3, March 2008, 252–255), it is difficult to separate and purify it, which limits its applicability, so the development of new and efficient total synthesis of salvianolic acid N The method has important practical application value. (3...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D313/14
CPCC07D313/14Y02P20/55
Inventor 崔冬梅谢中袍吴空张辰
Owner ZHEJIANG UNIV OF TECH