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Chiral beta-diester selenide compound, and preparation method thereof through Michael addition

A compound and diester technology, which is applied in the field of preparation of chiral beta-diester selenide compounds and their Michael addition, can solve the problems of low enantioselectivity, limited substrates and the like, and achieve simplified operation steps, High reaction efficiency, safe and controllable reaction process

Pending Publication Date: 2021-11-09
SHENZHEN BAY LAB +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of this application is to provide a preparation method for chiral β-diester selenides and their Michael addition, aiming to solve the existing asymmetric selenium Michael addition with limited substrates and low enantioselectivity The problem

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  • Chiral beta-diester selenide compound, and preparation method thereof through Michael addition
  • Chiral beta-diester selenide compound, and preparation method thereof through Michael addition
  • Chiral beta-diester selenide compound, and preparation method thereof through Michael addition

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preparation example Construction

[0070] The second aspect of the embodiment of the present application provides a preparation method of Michael addition of chiral β-diester selenide compounds, comprising the following steps:

[0071] S01. Selenol compound A and ene diester compound B shown in the general structural formula are provided:

[0072] A:R 1 -SeH B:

[0073] S02. Adding the selenol compound A and the olefin diester compound B into a reaction system containing a nitrogen heterocyclic carbene catalyst, an alkaline reagent and a water-absorbing additive, and reacting at a temperature of -100°C to 25°C, A chiral β-diester selenide compound represented by formula I is obtained.

[0074] Specifically, in the above step S01, R in the molecular structural formula of selenol compound A 1 The represented group is the same as R in the general formula I of the molecular structure of the above chiral β-diester selenide compound 1 The groups represented are the same. R in the molecular structural formula o...

Embodiment 1

[0094] This example provides a diethyl (R)-2-(2-(hexylselenyl)-2-(4-methoxyphenyl)ethyl)malonate and a preparation method thereof. The structural formula of the ((R)-2-(2-(hexylselenyl)-2-(4-methoxyphenyl)ethyl)diethyl malonate is shown in molecular structural formula I1 below:

[0095]

[0096] Its preparation steps are as follows:

[0097] In a 20ml test tube, dissolve triazolecarbene-thiourea bifunctional catalyst (0.01mmol, 0.1 equivalent (equiv.)), 13X molecular sieve (100mg) and n-hexylselenol nucleophile (0.2mmol, 2.0equiv.), In a mixed solvent of 1.2 mL of pretreated diethyl ether, seal it with a rubber stopper, then replace the gas (3 times) under an argon atmosphere, and slowly add lithium bis(trimethylsilyl)amide (LiHMDS) (1mol / L, tetrahydrofuran / ethylbenzene solution, 10 μL, 0.10 equiv.), the gas was replaced again under argon atmosphere (3 times). The tube was sealed with Parafilm and then stirred at -90°C for 1 hour. Diethyl (E)-2-(4-methoxystyryl)malonate...

Embodiment 2

[0100]This example provides a diethyl (R)-2-(2-(4-methoxyphenyl)-2-(neopentylselenoyl)ethyl)malonate and a preparation method thereof. The structural formula of the (R)-2-(2-(4-methoxyphenyl)-2-(neopentylselenoyl) ethyl) malonate diethyl malonate is shown in molecular structural formula I2 below:

[0101]

[0102] Its preparation method refers to the preparation method of (R)-2-(2-(hexylselenyl)-2-(4-methoxyphenyl)ethyl)diethyl malonate in Example 1, the difference is Neopentylselenol (0.2 mmol) was used instead of n-hexylselenol. The reaction solution was directly separated and purified by silica gel column chromatography (ethyl acetate and n-hexane as eluents) to obtain the target product, a colorless liquid, with a yield of 96% and an ee value of 95%.

[0103] The prepared product I2 is subjected to characterization data analysis, and the result is 1 H NMR (400MHz, CD 2 Cl 2 )δ7.23(d, J=8.6Hz, 2H), 6.83(d, J=8.6Hz, 2H), 4.45(d, J=11.7Hz, 1H), 4.30-4.17(m, 2H), 4.03- ...

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Abstract

The invention relates to the technical field of synthesis of organic compounds, and particularly provides a chiral beta-diester selenide compound and a preparation method thereof through Michael addition. The molecular structure general formula of the chiral beta-diester selenide compound is shown in the specification formula I. The chiral beta-diester selenide compound has high functional group property and structural diversity, so that diversified choices can be provided for the application of the chiral beta-diester selenide compound in drug intermediate synthesis and functional materials, and the method is particularly applied to synthesis of malonate products and preparation of functional materials.

Description

technical field [0001] The application belongs to the technical field of organic compound synthesis, and in particular relates to a chiral β-diester selenide compound and a preparation method thereof by Michael addition. Background technique [0002] Selenium is a trace element, and chemists have paid increasing attention to organoselenium compounds, which have a significant impact on medicinal chemistry, materials chemistry, chemical biology, biochemistry and other fields. However, chiral organoselenium compounds are mainly synthesized from chiral substrates or controlled by chiral catalysts. The method controlled by chiral substrates has achieved remarkable development, but less attention has been paid to the strategy of asymmetric catalytic synthesis. [0003] At present, the existing asymmetric Michael addition of selenium mainly utilizes the electrophile or nucleophile of selenium. The reported selenium Michael reaction is the addition of aryl selenol Michael to enone ...

Claims

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Application Information

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IPC IPC(8): C07C391/00
CPCC07C391/00C07B2200/07
Inventor 黄湧陈杰安李恩
Owner SHENZHEN BAY LAB
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