Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for efficiently preparing chiral boride based on mobile phase

A boride and mobile phase technology, applied in the field of efficient preparation of chiral borides based on mobile phase, can solve the problems of harsh reaction conditions, environmental pollution, high cost, etc., and achieve mild reaction conditions, improved preparation efficiency, and short reaction time. Effect

Pending Publication Date: 2022-08-09
HUBEI ENG UNIV
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The catalyst consumption of this method is low and can be recycled, but the ability of cellulose complex copper in this invention is not ideal, can not realize recycling
And the chalcone substrate is insoluble in water, participates in the aqueous phase reaction in solid state, is not suitable for industrial production
[0004] Although the above methods have improved reactivity, they are also accompanied by problems such as harsh reaction conditions, high cost, environmental pollution, and inability to recycle catalysts, which greatly limit the application of such methods in actual production.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for efficiently preparing chiral boride based on mobile phase
  • Method for efficiently preparing chiral boride based on mobile phase
  • Method for efficiently preparing chiral boride based on mobile phase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] This embodiment provides a cellulose-supported Cu 2 O / TiO 2 The preparation method comprises the following steps:

[0057] P1. Add 20mL n-butyl titanate and 70mL absolute ethanol into the beaker, stir for 20min to obtain a yellow clear solution a; add 4mL glacial acetic acid, 20mL distilled water and 70mL absolute ethanol into the beaker, stir for 20min, and add dropwise 1mol / L HCl was adjusted to pH 3 to 4 to obtain solution b;

[0058] P2. Mix solution a and solution b obtained in step P1, stir in a water bath at 50 °C for 1 h to obtain a white gel, then place the white gel in an oven at 80 °C for 24 h to obtain yellow crystals, grind to obtain yellow powder, and then put The yellow powder was calcined at 600 °C for 2 h to obtain TiO 2 powder;

[0059] P3. Take 0.0802g NaOH and add it to 20mL distilled water, stir and dissolve to obtain NaOH solution; add 1mmol Cu(OAc) 2 Add to NaOH solution, stir and mix; then add 1 mmol of TiO obtained in step P2 2 And stir fo...

Embodiment 2

[0071] The present embodiment provides a method for efficiently preparing a chiral boride based on a mobile phase, comprising the following steps:

[0072] S1. The cellulose obtained in step P4 of Example 1 is loaded with Cu 2 O / TiO 2 The suspension was passed into the microchannel reactor until the entire reaction channel was filled, and then the microchannel reactor was placed in a drying oven at 150 °C to dry;

[0073] S2. Add 0.20 mmol α, β unsaturated ketone, 0.4 mmol biborate pinacol ester and 0.002 mmol ligand (R, S)-josiphos to 1 mL of toluene to pre-dissolve to obtain mixed solution c; The pressure of 120KPa continuously feeds distilled water and mixed solution c into the microchannel reactor, and the volume ratio of distilled water and mixed solution c is 9:1;

[0074] The α,β unsaturated ketone of this embodiment is chalcone (I-1), and the reaction formula in step S2 is as follows:

[0075]

[0076] S3. Collect the reaction solution at the sample outlet, extra...

Embodiment 3

[0088] This example is basically the same as Example 2, except that the α,β unsaturated ketone in this example is 3-(4-methylphenyl)-1-phenyl-2-propen-1-one ( I-2), the reaction formula is as follows in step S2:

[0089]

[0090] The chiral boride II-2 obtained by the preparation method in this example is 41.53 mg, the yield is 93%, and the ee value reaches 98%.

[0091] The reaction formula for the conversion of chiral boride II-2 to chiral hydroxyl compound III-2 is as follows:

[0092]

[0093] The H NMR and C NMR spectra of the chiral hydroxyl compound III-2 in this example are as follows:

[0094] 1 H NMR (400 MHz, Chloroform-d); δ=7.98–7.94 (m, 2H), 7.65–7.58 (m, 1H), 7.50–7.47 (m, 2H), 7.34–7.31 (m, 2H), 7.20– 7.18 (m, 2H), 5.33–5.29 (m, 1H), 3.63 (br, 1H), 3.40–3.30 (m, 2H), 2.34 (s, 3H).

[0095] 13 C NMR (100 MHz, Chloroform-d); δ=200.3, 140.0, 137.8, 136.5, 133.6, 129.2, 128.7, 128.2, 125.9, 69.9, 47.4, 21.5.

[0096] The high-performance liquid phase da...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for efficiently preparing chiral boride based on a mobile phase, and belongs to the technical field of organic synthesis. Comprising the following steps: S1, adding alpha, beta unsaturated ketone, bis (pinacolato) diboron and a ligand into toluene, and dissolving to obtain a mixed solution; and S2, filling a microchannel reactor with a cellulose-loaded Cu2O / TiO2 catalyst, continuously introducing distilled water and the mixed solution obtained in the step S1 into the microchannel reactor, carrying out an asymmetric boronation reaction, collecting a product, and carrying out separation and purification to obtain the chiral boride. According to the invention, TiO2 is added into the catalytic material, so that the amount and the stability of copper loaded on cellulose are improved, and the loaded copper is ensured not to be washed away in a mobile phase; toluene is used as an additive, and alpha, beta unsaturated ketone, bis (pinacolato) diboron and a ligand are pre-dissolved by using toluene; under the combined action of the two aspects, the non-boron-forming addition reaction of the alpha and beta unsaturated ketones can be completed in the mobile phase.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for efficiently preparing a chiral boride based on a mobile phase. Background technique [0002] In recent years, the application of chiral borides in medicinal chemistry and synthetic chemistry has attracted extensive attention. Therefore, how to efficiently construct chiral borides has become a research hotspot. Transition metal-catalyzed enantioselective boron addition to α,β-unsaturated acceptors is an efficient way to synthesize chiral borides, among which copper-catalyzed enantioselective boron addition to α,β-unsaturated acceptors has The catalyst is cheap and easy to obtain, the amount of ligand is small, and the enantioselectivity of the product is good, which has become the focus of research. [0003] But so far, the reaction conditions of copper-catalyzed enantioselective boron addition reaction of α,β-unsaturated acceptors are still very complex a...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02B01J23/72B01J31/06B01J31/24
CPCC07F5/025B01J31/06B01J31/2414B01J23/72B01J23/002B01J2531/842B01J2231/323C07B2200/07Y02P20/584
Inventor 张瑶瑶朱磊李博解李维双汪连生
Owner HUBEI ENG UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com