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Unsaturated carbonyl compounds as well as preparation method and application thereof

A carbonyl compound and unsaturated technology, which is applied in the field of unsaturated carbonyl compounds and their preparation, can solve the problems of harsh synthesis conditions of unsaturated carbonyl compounds, synthetic methods not universally applicable, complex processes, etc., and achieve a safe and controllable reaction process , avoid strong oxidative conditions, high application prospects

Active Publication Date: 2019-06-18
PEKING UNIV SHENZHEN GRADUATE SCHOOL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The invention provides an unsaturated carbonyl compound and a preparation method thereof to solve the technical problems of the existing unsaturated carbonyl compound, such as harsh synthesis conditions, low yield, complicated process and non-universal synthesis method

Method used

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  • Unsaturated carbonyl compounds as well as preparation method and application thereof
  • Unsaturated carbonyl compounds as well as preparation method and application thereof
  • Unsaturated carbonyl compounds as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0077] In one embodiment, the preparation method of the unsaturated carbonyl compound includes the following steps:

[0078] S01: Provide γ,δ-unsaturated carbonyl compound A represented by the following structural formula:

[0079]

[0080] S02: The γ, δ-unsaturated carbonyl compound A is added to a reaction system containing transition metal catalysts, additives and oxidants, and reacted at 10 to 150°C to obtain the following general structural formula as shown in formula (I) Of unsaturated carbonyl compounds,

[0081]

[0082] Specifically, in the above step S01, the R in the γ, δ-unsaturated carbonyl compound A 1 , R 2 , R 3 And R 4 Are the same or different hydrogen atoms, C 1 -C 20 Alkyl, C 1 -C 20 Heteroalkyl, C 3 -C 20 Cycloalkyl, C 3 -C 20 Heterocycloalkyl, C 2 -C 20 Alkenyl, C 2 -C 20 Heteroalkenyl, C 3 -C 20 Cycloalkenyl, C 3 -C 20 Heterocyclenyl, C 2 -C 20 Alkynyl, C 2 -C 20 Heteroalkynyl, C 3 -C 20 Cycloalkynyl, C 3 -C 20 Heterocycloalkynyl, C 1 -C 20 Alkoxy, aryl, substi...

Embodiment 1

[0113] This Example 1 provides a (E)-N-(4-methoxybenzyl)-2,4-dienepentanamide and a preparation method thereof.

[0114] The structural formula of (E)-N-(4-methoxybenzyl)-2,4-dienpentylamide is shown in the following molecular structure I1:

[0115]

[0116] The preparation steps are as follows:

[0117] In a dry 10mL test tube, add transition metal iridium catalyst (0.002mmol, 0.02eq), silver tetrafluoroborate additive (0.005mmol, 0.05eq), copper acetate monohydrate (0.004mmol, 0.04eq), corresponding N-(4 -Methoxybenzyl)-4-enepentanamide substrate and 1.0 mL of anhydrous 1,4-dioxane. The reaction tube was sealed and the air was replaced six times. The resulting mixture was stirred at 60°C for 12 hours.

[0118] After the reaction, the reaction solution was filtered through a glass dropper containing silica gel, washed with dichloromethane, and the filtrate was spin-dried to obtain the target product I1, a white solid, with a yield of> 99%.

[0119] NMR characterization analysis, the r...

Embodiment 2

[0121] This example 2 provides a (2E, 4E)-N-(thiophen-3-methylene)-2,4-diene octamide and a preparation method thereof.

[0122] The structural formula of the (2E,4E)-N-(thiophen-3-methylene)-2,4-dienoctamide is shown in the following molecular structural formula I2:

[0123]

[0124] The preparation steps are as follows: In a dry 10mL test tube, add transition metal iridium catalyst (0.002mmol, 0.02eq), silver tetrafluoroborate additive (0.005mmol, 0.05eq), copper acetate monohydrate (0.004mmol, 0.04eq), corresponding (E)-N-(thiophen-3-methylene)-4-enoctamide substrate and 1.0 mL of anhydrous 1,4-dioxane, the reaction tube is sealed and the air is replaced six times, the resulting mixture Stir at 60°C for 20 hours.

[0125] After the reaction, the reaction solution was filtered through a glass dropper containing silica gel, washed with dichloromethane, and the filtrate was spin-dried to obtain the target product I2, a white solid, with a yield of 95%.

[0126] NMR characterization a...

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Abstract

The invention discloses unsaturated carbonyl compounds as well as a preparation method and application thereof. A general formula of the molecular structures of the unsaturated carbonyl compounds is shown in a formula (I); the preparation method of the unsaturated carbonyl compounds comprises the steps of adding a gamma, delta-unsaturated carbonyl compound A into a reaction system containing a transition metal catalyst, an additive and an antioxidant to react and the like. The unsaturated carbonyl compounds disclosed by the invention have two continuous double bonds and carbonyl functional groups; a large quantity of compounds having a special functionalization center can be obtained through simple chemical conversion; the preparation method of the compounds is simple in technology, low inreaction condition requirements, safe and controllable in reaction process, and high in utilization ratio of atoms and production efficiency; meanwhile, the regioselectivity of a product is efficiently ensured; the environmental pollution pressure of a methodology is low through the introduction of a concept of direct dehydrogenation by oxidation of carbonyl compounds with air; and the method iswidely applicable to the preparation of natural products and drug molecular intermediates.

Description

Technical field [0001] The invention belongs to the technical field of organic compound synthesis, and specifically relates to an unsaturated carbonyl compound and a preparation method and application thereof. Background technique [0002] Unsaturated carbonyl compounds (α, β-unsaturated carbonyl compounds) refer to structures such as (O=CR)-C α =C β -R shows a class of carbonyl compounds. Unsaturated carbonyl compounds are an extremely important organic synthon. Starting from the products of unsaturated carbonyl compounds, using known chemical methods to modify them is an important part of the development of natural products and new drug molecules. [0003] Among them, unsaturated amides and unsaturated carboxylic acids are an important category of unsaturated carbonyl compounds. Unsaturated amides and unsaturated carboxylic acids are important building blocks for natural products and new drug molecular intermediates. The classical method of synthesis of unsaturated carbonyl co...

Claims

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Application Information

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IPC IPC(8): C07B35/04C07C231/12C07C233/27C07C233/15C07C233/09C07C233/29C07C253/30C07C255/23C07C51/377C07C57/03C07C57/42C07C45/65C07C49/794C07D333/20C07D263/26C07D295/185C07C259/06C07D317/60C07D313/00C07D215/38
Inventor 黄湧王珍陈杰安
Owner PEKING UNIV SHENZHEN GRADUATE SCHOOL
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