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Diyne enamine compound and its preparation method and application

A technology of diacetylenic enamines and compounds is applied in the field of enamine compound synthesis, and can solve the problems of complex process, unfriendly environment, harsh preparation conditions and the like

Active Publication Date: 2021-08-20
PEKING UNIV SHENZHEN GRADUATE SCHOOL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a method for preparing diacetylene enamine compounds to overcome the technical problems of harsh preparation conditions, low yield, complex process, unfriendly environment, and limited application range of existing highly conjugated enamine compounds.

Method used

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  • Diyne enamine compound and its preparation method and application
  • Diyne enamine compound and its preparation method and application
  • Diyne enamine compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0122] This embodiment provides a trans-1-(4-phenyl-1,6-bis(triisopropylsilyl)hexyl-3-en-1,5-diyne-3)pyrrolidine and its Preparation.

[0123] The structural formula of the trans-1-(4-phenyl-1,6-bis(triisopropylsilyl)hexyl-3-ene-1,5-diyne-3)pyrrolidine is shown in the following molecular structure formula I1 :

[0124]

[0125] Its preparation steps are as follows:

[0126] Add 1-phenyl-4-triisopropylsilyl-butane-3-yn-2-one (0.1mmol, 1.0eq), bipyridine (0.02mmol, 0.2eq) into a dry sealed 10mL tube, Triisopropylsilyl-alkynyl iodide ketone (0.12mmol, 1.2eq) and 2mL of anhydrous diethyl ether were added successively to gold chloride (0.01mmol, 0.1eq) and pyrrolidine (0.12mmol, 1.2eq), and placed The reaction time at 50°C is 10h.

[0127] After the reaction was completed, the filtrate was spin-dried and separated by column chromatography to obtain the target product as a bright yellow oily liquid with a yield of 88%. Trans product: cis product>20:1.

[0128] Correlation re...

Embodiment 2

[0130] This example provides a trans-1-(4-m-methylbenzene)-1,6-bis(triisopropylsilyl)hexyl-3-ene-1,5-diyne-3)pyrrole Alkanes and their preparation methods.

[0131] The structural formula of the trans-1-(4-m-methylphenyl-1,6-bis(triisopropylsilyl)hexyl-3-ene-1,5-diyne-3)pyrrolidine is as follows molecular structural formula I2 shows:

[0132]

[0133] Its preparation method refers to the preparation of trans-1-(4-phenyl-1,6-bis(triisopropylsilyl)hexyl-3-ene-1,5-diyne-3)pyrrolidine in Example 1 method, except that 1-(3-methyl-phenyl)-4-triisopropylsilyl-butane-3-yn-2-one (0.1 mmol) was used instead of 1-phenyl-4- Triisopropylsilyl-butan-3-yn-2-one.

[0134] After the reaction was completed, the filtrate was spin-dried and separated by column chromatography to obtain the target product as a bright yellow oily liquid with a yield of 86%. Trans product: cis product = 10.2:1.

[0135] The product I2 prepared is subjected to characterization data analysis, and the result is: ...

Embodiment 3

[0137] This example provides a trans-1-(4-p-methylphenyl-1,6-bis(triisopropylsilyl)hexyl-3-ene-1,5-diyne-3)pyrrole Alkanes and their preparation methods.

[0138] The structural formula of trans-1-(4-p-methylphenyl-1,6-bis(triisopropylsilyl)hexyl-3-en-1,5-diyne-3)pyrrolidine is as follows Molecular structure formula I3 Shown:

[0139]

[0140] Its preparation method refers to the preparation of trans-1-(4-phenyl-1,6-bis(triisopropylsilyl)hexyl-3-ene-1,5-diyne-3)pyrrolidine in Example 1 method, except that 1-(4-methyl-phenyl)-4-triisopropylsilyl-butane-3-yn-2-one (0.1 mmol) was used instead of 1-phenyl-4- Triisopropylsilyl-butan-3-yn-2-one.

[0141] After the reaction was completed, the filtrate was spin-dried and separated by column chromatography to obtain the target product as a bright yellow oily liquid with a yield of 82%. Trans product: cis product = 9.1:1.

[0142]The product I3 prepared is subjected to characterization data analysis, and the result is: 1 H NMR (...

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Abstract

The invention discloses a diyne enamine compound, a preparation method and application thereof. The general molecular structure formula of the diyne enamine compound of the present invention is described in the general formula (I) in the description. The preparation method of the diacetylene amine compound comprises the steps of adding a secondary amine A and a gold catalyst into a reaction system containing an electrophile compound B, a pyridine ligand C and an acetylenic compound D for reaction. The diyne enamine compound of the present invention contains a highly conjugated enamine structure skeleton, which is convenient for further functionalization, and can be widely used in the synthesis and preparation of pharmaceutical intermediates, especially polycyclic compounds. The preparation method has simple process, low requirements on reaction conditions, safe and controllable reaction process, high atom utilization rate and production efficiency, and at the same time, the regio and stereoselectivity of the product can be efficiently guaranteed, and the introduction of the concept of organometallic catalysis makes the methodological Environmental pollution pressure is small.

Description

technical field [0001] The invention belongs to the technical field of synthesis of enamine compounds, and in particular relates to a diacetylene enamine compound, a preparation method thereof and an application of the diacetylenamine compound. Background technique [0002] A highly conjugated enamine compound refers to an enamine compound containing a highly conjugated π system in its molecular structure. Highly conjugated enamine compounds are not only extremely important pharmaceutical fragments and intermediates, but also potential bioactive molecules. Using highly conjugated enamine compounds as reaction intermediates and modifying them with known chemical means is an important part of the research and development of new drug molecules. Due to their poor stability, the existing enamine compounds usually face difficulties in separation and synthesis. The classic synthesis methods often face high reaction temperatures, harsh reaction conditions, low yields, complicated p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/08
Inventor 黄湧彭思宇汪兆丰陈杰安
Owner PEKING UNIV SHENZHEN GRADUATE SCHOOL
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