Unsaturated carbonyl compound and its preparation method and application

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, unapplicable synthesis methods, complicated processes, etc., and achieves a safe and controllable reaction process. , Avoid strong oxidizing conditions, the effect of simple process

Active Publication Date: 2022-05-06
PEKING UNIV SHENZHEN GRADUATE SCHOOL
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  • Abstract
  • Description
  • Claims
  • Application Information

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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 compound and its preparation method and application
  • Unsaturated carbonyl compound and its preparation method and application
  • Unsaturated carbonyl compound and its preparation method and application

Examples

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preparation example Construction

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

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

[0079]

[0080] S02: Add the γ, δ-unsaturated carbonyl compound A into a reaction system containing a transition metal catalyst, additives and oxidant, and react at 10-150°C to obtain the following general structure as shown in formula (I) of unsaturated carbonyl compounds,

[0081]

[0082] Specifically, in the above step S01, R in the γ, δ-unsaturated carbonyl compound A 1 , R 2 , R 3 and R 4 For 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 -C20 Heterocycloalkenyl, C 2 -C 20 Alkynyl, C 2 -C 20 Heteroalkynyl, C 3 -C 20 Cycloalkynyl, C 3 -C 20 Heterocycloalkynyl, C 1 -...

Embodiment 1

[0113] Example 1 provides (E)-N-(4-methoxybenzyl)-2,4-dienyl valeramide and its preparation method.

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

[0115]

[0116] Its preparation steps are as follows:

[0117]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-valeramide substrate and 1.0 mL of anhydrous 1,4-dioxane, the reaction tube was sealed and replaced with air six times, and the resulting mixture was stirred at 60°C for 12 hours.

[0118] After the reaction was completed, the reaction solution was filtered through a glass dropper containing silica gel, rinsed 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...

Embodiment 2

[0121] Example 2 provides a (2E,4E)-N-(thiophene-3-methylene)-2,4-diene octanamide and a preparation method thereof.

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

[0123]

[0124] Its preparation steps are as follows: 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-(thiophene-3-methylene)-4-ene octanamide substrate and 1.0 mL of anhydrous 1,4-dioxane, the reaction tube was sealed and replaced with air six times, the resulting mixture Stir at 60°C for 20 hours.

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

[0126] NMR characteriz...

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Abstract

The invention discloses an unsaturated carbonyl compound, a preparation method and application thereof. The general formula of the molecular structure of the unsaturated carbonyl compound is shown in the following formula (I): the preparation method of the unsaturated carbonyl compound comprises adding gamma, the δ-unsaturated carbonyl compound A to the compound containing transition metal catalyst, additive and oxidizing agent Steps such as reaction are carried out in the reaction system. The unsaturated carbonyl compound of the present invention has two continuous double bonds and carbonyl functional groups, and a large number of compounds with special functional group centers can be obtained through simple chemical transformation. The preparation method is simple, has low requirements on reaction conditions, and the reaction process is safe and reliable. control, atom utilization and production efficiency are high, and the regioselectivity of the product is guaranteed at the same time, and the introduction of the concept of direct dehydrogenation of carbonyl compounds by air oxidation makes the environmental pollution pressure of this methodology small, and can be widely used in natural products and drug molecules Preparation of intermediates.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to an unsaturated carbonyl compound and its preparation method and application. Background technique [0002] Unsaturated carbonyl compounds (α, β-unsaturated carbonyl compounds) refer to those with a structure such as (O=CR)-C α =C β A class of carbonyl compounds represented by -R. Unsaturated carbonyl compounds are extremely important organic synthons. Starting from the unsaturated carbonyl compound product, using known chemical means to modify it is an important part of the research and development of natural products and new drug molecules. [0003] Among them, unsaturated amides and unsaturated carboxylic acids are important types of unsaturated carbonyl compounds. Unsaturated amides and unsaturated carboxylic acids are an important class of building blocks for natural products and novel drug molecular intermediates. The classic method of syn...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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