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Hexahydroisoindole-1-keto compound and synthetic method thereof

A technology for hexahydroisoindole and ketone compounds, which is applied in organic chemistry and other fields, and can solve problems such as the limitation of synthesis efficiency

Inactive Publication Date: 2009-12-16
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a compound library synthesis method, the synthesis efficiency is limited

Method used

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  • Hexahydroisoindole-1-keto compound and synthetic method thereof
  • Hexahydroisoindole-1-keto compound and synthetic method thereof
  • Hexahydroisoindole-1-keto compound and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] (3aS * , 6R * , 7R * , 7aR * Synthesis of )-2,3,3a,6,7,7a-hexahydro-2-(4-methoxybenzyl)-6-phenyl-7-benzoyl-1H-isoindol-1-one Proceed as follows:

[0052] (2E, 4E)-N-(4-methoxybenzyl)-5-phenylpenta-2,4-dienyl α-bromoacetamide (114 mg, 0.28 mmol) in THF-water mixed solution (H 2 (0:THF=1:10, 3ml) was added triphenylphosphine (88 mg, 0.34mmol), potassium carbonate (58 mg, 0.42mmol) and hydrated acetophenone aldehyde (51 mg, 0.34mmol), and the mixture The reaction was stirred at room temperature for 6 hours. The reaction mixture was diluted with 10 mL of ethyl acetate, washed successively with saturated aqueous ammonium chloride solution and saturated brine (5 mL each), and the combined aqueous phase was extracted with ethyl acetate (3×5 mL). After combining the organic phases with anhydrous Na 2 SO 4 Dry, filter, and remove the solvent under reduced pressure to obtain a crude product, which is purified by silica gel column chromatography with a petroleum ether sol...

Embodiment 2

[0054] (3aS * , 6R * , 7R * , 7aR * Synthesis of )-2,3,3a,6,7,7a-hexahydro-2-(4-methoxybenzyl)-6-phenyl-7-ethoxycarbonyl-1H-isoindol-1-one

[0055] Mixed solution of (2E, 4E)-N-(4-methoxybenzyl)-5-phenylpenta-2,4-dienyl α-bromoacetamide (60 mg, 0.15 mmol) in tetrahydrofuran-water (H 2(0:THF=2:1, 2ml) was added triphenylphosphine (59mg, 0.22mmol), potassium carbonate (22mg, 0.16mmol) and ethyl glyoxylate (46mg, 0.45mmol), and the mixture The reaction was stirred at room temperature for 48 hours. Carry out aftertreatment by the method for embodiment 1, obtain product (3aS * , 6R * , 7R * , 7aR * )-2,3,3a,6,7,7a-hexahydro-2-(4-methoxybenzyl)-6-phenyl-7-ethoxycarbonyl-1H-isoindol-1-one 29 mg , the yield was 48%. colorless oil; 1 H NMR (400MHz, CDCl 3 )δ7.32-7.21(m, 3H), 7.20-7.12(m, 4H), 6.86(d, J=8.4Hz, 2H), 6.02(d, J=9.6Hz, 1H), 5.71(ddd, J =9.6, 3.2, 3.2Hz, 1H), 4.49 and 4.25(ABq, J=14.4Hz, 2H), 4.02-3.96(m, 1H), 3.80(s, 3H), 3.78-3.64(m, 2H), 3.31(dd, J=9.2, 7.2...

Embodiment 3

[0057] (3aS * , 6R * , 7R * ,7aS * )-2,3,3a,6,7,7a-hexahydro-2-(4-methoxybenzyl)-6,7-diphenyl-1H-isoindol-1-one and (3aS * , 6R * ,7S * , 7aR * Synthesis of )-2,3,3a,6,7,7a-hexahydro-2-(4-methoxybenzyl)-6,7-diphenyl-1H-isoindol-1-one

[0058] Will contain (2E, 4E)-N-(4-methoxybenzyl)-5-phenylpenta-2,4-dienyl α-bromoacetamide (32 mg, 0.08 mmol,), triphenyl Phosphine (26 mg, 0.10mmol), potassium carbonate (17 mg, 0.12mmol) and benzaldehyde (17 mg, 0.16mmol) in tetrahydrofuran-water mixed solution (H 2 (0:THF=1:1, 1 ml) microwave reaction tube was capped and sealed, stirred and reacted at room temperature for 15 hours, and then heated by microwave at 180° C. for 0.5 hour. Carry out aftertreatment by the method for embodiment 1, obtain product (3aS * , 6R * , 7R * ,7aS * )-2,3,3a,6,7,7a-hexahydro-2-(4-methoxybenzyl)-6,7-diphenyl-1H-isoindol-1-one 23 mg, yield 70%. colorless oil; 1 H NMR (400MHz, CDCl 3 )δ7.17(d, J=8.4Hz, 2H), 7.10-7.03(m, 6H), 6.87(d, J=8.8Hz, 2H),...

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Abstract

The invention discloses a hexahydroisoindole-1-keto compound and a synthetic method thereof. The structure of hexahydroisoindole-1-keto is as a formula (I) or a formula (II), or an enantiomer of the formula (I) or the formula (II), wherein in the formula, R is hydrogen, methyl or aryl; R is hydrogen or methyl; R is benzyl or p-methoxybenzyl; and R is hydrogen, methyl, alkoxycarbonyl, benzoyl or aryl. The synthetic method for the hexahydroisoindole-1-keto comprises that: 2, 4-pentadieneamine is firstly condensed with alpha-bromoacetic acid to generate corresponding alpha-bromoacetamide, and then the alpha-bromoacetamide reacts with aldehyde to obtain the hexahydroisoindole-1-keto under the conditions of proper solvent and temperature in the presence of triphenylphosphine and inorganic alkali. The hexahydroisoindole-1-keto compound and the synthetic method thereof can be used for bioactivity screening or medicament development.

Description

technical field [0001] The present invention relates to nitrogen-containing bicyclic compounds and their synthetic method, be specifically related to utilize and carry out " one pot method " Wittig-Diels-Alder (Wittig-Diels-Alde) by α-bromoacetamide containing diene structure and aldehyde Alder) reaction to carry out the synthesis method and its product. Background technique [0002] The hexahydroisoindole unit exists as a dominant structure in many natural compound molecules and drug molecules. Hexahydroisoindole appears more often in natural compounds, especially Cytochalasin compounds, in the form of hexahydroisoindol-1-one structural units. This type of compound belongs to the secondary metabolites of fungi, and can be isolated from many different fungi. At present, there are more than 80 compounds with different structures. They have numerous biological activities, such as some can prevent cell division and cause cell apoptosis (Carter, S.B. Effects of Cytochalasins o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/46
Inventor 吴金龙赵健戴伟民
Owner ZHEJIANG UNIV
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