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Synthesis method of valerolactam alkaloid compound

A technology of alkaloids and valerolactam, applied in organic chemistry and other directions, can solve the problems of small amount and inability to carry out other activity research, and achieve the effects of simple operation, cheap and easily available reagents, and mild reaction conditions.

Inactive Publication Date: 2019-08-09
XI AN JIAOTONG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Valerolactam alkaloid is a new compound extracted and isolated from plants. The experimental results show that the compound has good anti-inflammatory activity, but the amount is very small, so it is impossible to conduct other activity research and more in-depth mechanism research.

Method used

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  • Synthesis method of valerolactam alkaloid compound
  • Synthesis method of valerolactam alkaloid compound
  • Synthesis method of valerolactam alkaloid compound

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Embodiment 1

[0043] A kind of synthetic method of valerolactam alkaloid compound, comprises the following steps:

[0044] 1) ferulic acid obtains ferulic acid methyl ester by esterification

[0045] In an ice-water bath, 3 g (25.7 mmol) of thionyl chloride was added to an eggplant-shaped flask containing 50 ml of anhydrous methanol, and stirred for 30 min. Then, 5 g (25.7 mmol) of ferulic acid dissolved in 40 ml of methanol was added into the reaction system, and the reaction was stirred for 5 h.

[0046] After the reaction is complete, concentrate under reduced pressure, elute the product with 100ml ethyl acetate and then extract once with 20ml saturated brine, then dry the organic layer with anhydrous sodium sulfate, filter with suction, concentrate the filtrate, and finally use petroleum ether: ethyl acetate Esters=20:1 Passed through a silica gel column to obtain 5 g (24 mmol) of methyl ferulate, with a yield of 93.4%.

[0047] 2) Methyl ferulate is reduced by diisobutyl aluminum hyd...

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Abstract

The invention discloses a synthesis method of a valerolactam alkaloid compound. The method comprises the steps that 1) thionyl chloride reacts with methanol, and then ferulic acid is added to synthesize ferulic acid methylester; 2) the ferulic acid methylester reacts under the function of diisobutylaluminum hydride to generate coniferyl alcohol; 3) 2-piperidone reacts with phosphorus pentachloride, and then a reaction product reacts with bromine under the function of potassium iodide to generate 3,3-dibromo-2-piperidone; 4) the 3,3-dibromo-2-piperidone reacts with hydrogen and sodium acetate under the function of palladium carbon to generate 3-bromo-2-piperidone; 5) the 3-bromo-2-piperidone prepared in the fourth step reacts with the coniferyl alcohol prepared in the second step under thefunction of sodium hydroxide to generate the valerolactam alkaloid compound. The synthesis method has the advantages that the sources of the raw materials are easy to obtain, the reaction conditions are mild, and the operation in the reaction process is simple.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a method for synthesizing valerolactam alkaloid compounds. Background technique [0002] Lactam compounds widely exist in natural medicines and have important biological significance and research value. For example, the compound UK224671 containing a six-membered lactam skeleton has neurohormone 2 receptor antagonism; β-lactam antibiotics include penicillin, cephalosporin Bacterins, monoamide rings, etc., have the advantages of strong bactericidal activity, wide adaptability, and good clinical curative effect, and are currently the most widely used broad-spectrum antibacterial chemotherapy drugs in clinical practice; Nervous system control, cerebrovascular diseases and other aspects show special biological activity. [0003] Valerolactam alkaloid is a new compound extracted and isolated from plants. Experimental results show that this compound has good ant...

Claims

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Application Information

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IPC IPC(8): C07D211/76
CPCC07D211/76
Inventor 张海龙张昌龙高阳
Owner XI AN JIAOTONG UNIV
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