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PH sensitive catalyst for catalyzing asymmetric Aldol reaction and preparation method thereof

A catalyst, asymmetric technology, used in catalytic reactions, preparation of organic compounds, catalysts for physical/chemical processes, etc., to achieve high-efficiency catalytic effects

Active Publication Date: 2021-09-17
BEIJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although these intelligent responsive nanomaterials have potential application prospects in the field of drug sustained and controlled release, however, the use of polyacrylic acid to modify BMMs, and then by loading catalytically active chiral molecules to achieve controlled release activity under different pH conditions species and used to catalyze asymmetric Aldol reactions are rarely reported

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  • PH sensitive catalyst for catalyzing asymmetric Aldol reaction and preparation method thereof
  • PH sensitive catalyst for catalyzing asymmetric Aldol reaction and preparation method thereof
  • PH sensitive catalyst for catalyzing asymmetric Aldol reaction and preparation method thereof

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preparation example Construction

[0061] The invention provides a method for preparing a pH-sensitive catalyst for catalyzing an asymmetric Aldol reaction, comprising:

[0062] Using polyacrylic acid derivatives as the shell and mesoporous silica nanocarriers as the core; the carboxyl groups in the polyacrylic acid derivatives are activated and coupled with the amino groups on the mesoporous silica nanomaterial carrier through amidation Core-shell organic-inorganic nanomaterials were prepared by coating processes such as reaction, and chiral bipyridyl / biarylproline derivatives were loaded on the core-shell organic-inorganic nanomaterials to prepare asymmetric Aldol for catalytic pH-sensitive catalyst for the reaction.

[0063] Such as figure 1 Shown, above-mentioned preparation method specifically comprises:

[0064] Step 1. Preparation of chiral bipyridyl / biarylproline derivative Z; wherein,

[0065] Z was prepared according to the literature (Synlett, 2012, 23, (13): 1990-1994; Chemistry Select, 2020, 5, ...

Embodiment 1

[0087] The invention provides a method for preparing a pH-sensitive catalyst for catalyzing an asymmetric Aldol reaction, comprising:

[0088] Step 1. Prepare Z 1 , the molecular structure is as follows:

[0089]

[0090] Step 2. Preparation of BMMs (t-BMMs) without template removal agent CTAB:

[0091] Dissolve 2.62g of CTAB in 105mL of distilled water, stir magnetically until completely dissolved, pipette 8mL of tetraethyl orthosilicate (TEOS) and slowly add to the above solution, then quickly add 3.5mL of 25% ammonia water (NH 3 ·H 2 0), continue to stir until the solution all turns into white gel. The white gel was suction-filtered, washed thoroughly with distilled water, and dried to obtain BMMs without template release, which were designated as t-BMMs.

[0092] Step 3, prepare amino group modified t-BMMs:

[0093] Step 3.1. Weigh 0.5012 g of the t-BMMs sample obtained in step 2 into a round bottom flask, and dry it under vacuum at 150°C for 3 hours;

[0094] Ste...

Embodiment 2

[0113] The invention provides a method for preparing a pH-sensitive catalyst for catalyzing an asymmetric Aldol reaction, comprising:

[0114] Step 1. Prepare Z 2 , the molecular structure is as follows:

[0115]

[0116] Step 2. Preparation of BMMs (t-BMMs) without template removal agent CTAB:

[0117] Dissolve 2.81g of CTAB in 105mL of distilled water, stir magnetically until completely dissolved, pipette 8mL of TEOS and slowly add to the above solution, then quickly add 4.5mL of 25% NH 3 ·H 2 O, continue to stir until the solution turns into a white gel. The white gel was suction-filtered, washed thoroughly with distilled water, and dried to obtain BMMs without template release, which were designated as t-BMMs.

[0118] Step 3, prepare amino group modified t-BMMs:

[0119] Step 3.1. Weigh 0.5012 g of the t-BMMs sample obtained in step 2 into a round bottom flask, and dry it under vacuum at 150°C for 3 hours;

[0120] Step 3.2, disperse the above dried t-BMMs in anh...

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Abstract

The invention discloses a pH sensitive catalyst for catalyzing an asymmetric Aldol reaction and a preparation method thereof. The preparation method comprises the following steps: taking a polyacrylic acid derivative as a shell and a mesoporous silica nano-carrier as a core; and activating a carboxyl group in a polyacrylic acid derivative, carrying out amidation coupling reaction and other coating processes on the activated carboxyl group and an amino group on a mesoporous silica nano-material carrier to prepare a core-shell type organic-inorganic nano-material, and loading a chiral bipyridine / biaryl proline derivative on the core-shell type organic-inorganic nano-material to obtain the pH sensitive catalyst used for catalyzing the asymmetric Aldol reaction. The pH sensitive catalyst provided by the invention not only can solve the problem of poor dispersibility of Z on mesoporous surfaces and the like caused by easy aggregation of the mesoporous silica nano-carriers in a solution, but also can achieve an efficient catalytic effect by intelligently releasing the loaded active species Z in different pH environments in a catalytic process.

Description

technical field [0001] The invention relates to the technical field of catalysts, in particular to a pH-sensitive catalyst for catalyzing an asymmetric Aldol reaction and a preparation method thereof. Background technique [0002] In recent years, asymmetric Aldol reactions (aldol condensation reactions) have been widely recognized as the most important class of carbon-carbon bond formation reactions in organic synthesis. [0003] As early as 2000, List et al. (Journal of the American Chemical Society, 2000, 122, (10): 2395-2396) believed that chiral small molecule L-proline is also a class of "miniature aldolase" catalyst, which Catalytic asymmetric Aldol reaction under homogeneous conditions has remarkable characteristics such as simple operation and atom economy. Therefore, Zhao et al. (Synlett, 2012, 23, (13): 1990-1994) adopted various bipyridyl / biaryl prolines and their derivatives (Z) as homogeneous catalysts with excellent catalytic properties (products rates as hi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/02B01J31/06B01J35/02B01J35/08B01J35/10C07B53/00C07C201/12C07C205/45B01J35/00
CPCB01J31/069B01J31/0254B01J31/0245B01J31/0244C07B53/00C07C201/12B01J2231/4205C07B2200/07C07C2601/14B01J35/40B01J35/51B01J35/647C07C205/45Y02P20/584
Inventor 孙继红徐广鹏徐小欢白诗扬
Owner BEIJING UNIV OF TECH
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