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Synthetic method of polysubstituted 2,3-dihydrofuran compound

A technology for dihydrofuran and compounds, which is applied in the field of high-yield synthesis of 2,3-dihydrofuran compounds, achieving the effects of mild reaction conditions, simple operation and low price

Pending Publication Date: 2020-08-07
冯鞠花 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Curcumin has a β-diketone structure, so its analogues can be used as nucleophiles to react with chloronitroalkenes to synthesize dihydrofuran compounds. This method has not been reported yet

Method used

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  • Synthetic method of polysubstituted 2,3-dihydrofuran compound
  • Synthetic method of polysubstituted 2,3-dihydrofuran compound
  • Synthetic method of polysubstituted 2,3-dihydrofuran compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: the synthesis of compound 3a

[0023]

[0024] In a reaction tube, weigh curcumin analogue 1 (27.6 mg, 0.10 mmol), 1-chloro-1-nitro-2-styrene 2a (18.4 mg, 0.10 mmol), potassium carbonate (13.8 mg, 0.10 mmol ), added tetrahydrofuran (1.0 mL), 25 o The reaction was stirred under C for 24 hours, and the reaction of 1-chloro-1-nitro-2-styrene was monitored by thin layer chromatography. After removing the solvent under reduced pressure, separation and purification by flash column chromatography (petroleum ether: ethyl acetate: dichloromethane = 30:1:1), and 39.3 mg of yellow solid 3a was obtained with a yield of 93%.

[0025] 1 H NMR (400 MHz, CDCl 3 ) δ (ppm) 4.97 (s, 1 H), 5.90 (d, J = 4 Hz, 1H), 6.65 (d, J = 16 Hz, 1 H), 7.30-7.71 (m, 17 H), 7.96 (d, J = 16 Hz, 1 H); 13 C NMR (100MHz, CDCl 3 ) δ (ppm) 56.35, 109.39, 114.75, 115.22, 124.07, 127.37,128.25, 128.37, 128.90, 128.97, 129.77, 130.23, 130.58, 134.56, 135.36,137.70, 141.23, 143.42, 163....

Embodiment 2

[0026] Embodiment 2: the synthesis of compound 3b

[0027]

[0028] In a reaction tube, weigh curcumin analog 1 (27.6 mg, 0.10 mmol), 1-chloro-1-nitro-2-(4-methylphenyl)ethylene 2b (19.8 mg, 0.10 mmol), carbonic acid Potassium (13.8 mg, 0.10 mmol), added tetrahydrofuran (1.0 mL), 25 o The reaction was stirred under C for 24 hours, and the reaction of 1-chloro-1-nitro-2-(4-methylphenyl)ethylene was monitored by thin-layer chromatography. After removing the solvent under reduced pressure, separation and purification by flash column chromatography (petroleum ether: acetic acid Ethyl ester: dichloromethane = 30:1:1), to obtain 42.0 mg of yellow solid 3b with a yield of 96%.

[0029] 1H NMR (400 MHz, CDCl3) δ7.97 (d, J = 16.3 Hz, 1H), 7.80 – 7.50 (m,4H), 7.49 – 7.28 (m, 8H), 7.28 – 7.20 (m, 4H), 6.67 (d, J = 15.5 Hz, 1H), 5.88 (d, J = 1.6 Hz, 1H), 4.93 (br, 1H), 2.35 (s, 3H).

Embodiment 3

[0030] Embodiment 3: the synthesis of compound 3c

[0031]

[0032] In a reaction tube, weigh curcumin analogue 1 (27.6 mg, 0.10 mmol), 1-chloro-1-nitro-2-(3-methylphenyl)ethylene 2c (19.8 mg, 0.10 mmol), carbonic acid Potassium (13.8 mg, 0.10 mmol), added tetrahydrofuran (1.0 mL), 25 o The reaction was stirred under C for 24 hours, and the reaction of 1-chloro-1-nitro-2-(3-methylphenyl)ethylene was monitored by thin layer chromatography. After removing the solvent under reduced pressure, separation and purification by flash column chromatography (petroleum ether: acetic acid Ethyl ester: dichloromethane = 30:1:1), to obtain 39.8 mg of yellow solid 3c with a yield of 91%.

[0033] 1H NMR (400 MHz, CDCl3) δ 7.97 (d, J = 16.3 Hz, 1H), 7.75 – 7.55 (m,4H), 7.49 – 7.28 (m, 9H), 7.22 – 7.11 (m, 3H), 6.67 ( d, J = 15.5 Hz, 1H), 5.90 (d, J = 1.6 Hz, 1H), 4.92 (br, 1H), 2.37 (s, 3H).

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Abstract

The invention discloses a synthetic method of a polysubstituted 2,3-dihydrofuran compound, belonging to the field of organic chemistry. According to the method, curcumin analogues and chloronitroalkene are used as raw materials, a stirring reaction is carried out in the presence of a solvent and alkali, a reaction product is subjected to column chromatography separation, and the 2,3-dihydrofuran compound is obtained at a high yield. According to the synthetic method, a metal catalyst is not needed, reaction conditions are mild, operation is simple and convenient, the raw materials are easy toobtain, the yield is relatively high, and a new way is provided for synthesizing the polysubstituted 2,3-dihydrofuran compound.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a method for synthesizing 2,3-dihydrofuran compounds with high yield by using chloronitroalkenes and curcumin analogues as raw materials through Michael-alkylation reaction. Background technique [0002] 2,3-Dihydrofuran compounds are an important class of five-membered heterocyclic compounds. This ring structure has been widely found in biologically active natural products and drug molecules. For example, Isoplatydesmine is an ion channel blocker related to immune function (I. Butenschön, K. Möller, W. Hänsel, J. Med. Chem.2001, 44, 1249); Austocystin A is derived from corn flour A class of antifungal agents extracted (P. S. Steyn, R. Vleggaar, J. Chem. Soc., Perkin Trans. 1. 1974, 0, 2250); Clerodin has certain pharmacological effects and is an anthelmintic ( T. G. Kilroy, T. P. O'Sullivan, P. J. Guiry, Eur. J. Org. Chem. 2005, 2005, 4929); (+)-Eremantholi...

Claims

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Application Information

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IPC IPC(8): C07D307/30
CPCC07D307/30
Inventor 冯鞠花岳峻平王思源廉相金王博玉封金祥
Owner 冯鞠花
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