Novel compound as well as preparation method and application thereof

A compound and a new type of technology, applied in the field of new compounds and their preparation, can solve the problem of low enantioselectivity of hydrosilation products, achieve high yield, expand application, and inhibit the growth of weeds

Inactive Publication Date: 2016-03-16
YUNNAN MINZU UNIV
View PDF3 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The results show that our existing chiral ligands are not suitable for this reaction, and the enantioselectivity of the hydrosilylation product is not high, even zero

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
  • Novel compound as well as preparation method and application thereof
  • Novel compound as well as preparation method and application thereof
  • Novel compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] 1. In the glove box, put [Rh(COD)Cl] 2 (5mg, 0.01mmol) and 1 (129.6mg, 0.9mmol) were added to the reaction tube, and then 3mL of DCE was added, sealed and taken out. Use a syringe to add dimethylphenylsilane (690ul, 4.5mmol) to the reaction tube. Put it into an oil bath at a constant temperature of 90°C for 1 hour. After removing the solvent, petroleum ether / ethyl acetate 20:1 column chromatography gave 2, a white solid.

[0035] 2. Disperse 80 mg of KH (2 mmol) into 1 mL of NMP to make a suspension at 0°C. Add CHP (380 mg, 2 mmol) to the suspension, stir for 20 minutes, and then add dropwise to the reaction solution. 2 mL of NMP 2 (112 mg, 0.4 mmol) and TBAF (220 mg, 0.84 mg). After stirring for 10 minutes at room temperature, the temperature was raised to 70° C. and reacted for 5 hours. After cooling the reaction solution to room temperature, add 5 mL of saturated Na 2 S 2 O 3 The solution was stirred for 30 minutes. Extract with methyl tert-butyl ether (15 mL*5), co...

Embodiment 2

[0038] 1. In the glove box, put [Rh(COD)Cl] 2 (5mg, 0.01mmol) and 1 (129.6mg, 0.9mmol) were added to the reaction tube, and then 3mL of DCE was added, sealed and taken out. Use a syringe to add dimethylphenylsilane (690ul, 4.5mmol) to the reaction tube. Put it into an oil bath at a constant temperature of 90°C for 1 hour. After removing the solvent, petroleum ether / ethyl acetate 20:1 column chromatography gave 2, a white solid.

[0039] 2. Disperse 80 mg of KH (2 mmol) into 1 mL of NMP to make a suspension at 0°C. Add CHP (380 mg, 2 mmol) to the suspension, stir for 20 minutes, and then add dropwise to the reaction solution. 2 mL of NMP 2 (112 mg, 0.4 mmol) and TBAF (220 mg, 0.84 mg). After stirring for 10 minutes at room temperature, the temperature was raised to 70° C. and reacted for 5 hours. After cooling the reaction solution to room temperature, add 5 mL of saturated Na 2 S 2 O 3 The solution was stirred for 30 minutes. Extract with methyl tert-butyl ether (15 mL*5), co...

Embodiment 3

[0042] 1. In the glove box, put [Rh(COD)Cl] 2 (5mg, 0.01mmol) and 1 (129.6mg, 0.9mmol) were added to the reaction tube, and then 3mL of DCE was added, sealed and taken out. Use a syringe to add dimethylphenylsilane (690ul, 4.5mmol) to the reaction tube. Put it into an oil bath at a constant temperature of 90°C for 1 hour. After removing the solvent, petroleum ether / ethyl acetate 20:1 column chromatography gave 2, a white solid.

[0043] 2. Disperse 80 mg of KH (2 mmol) into 1 mL of NMP to make a suspension at 0°C. Add CHP (380 mg, 2 mmol) to the suspension, stir for 20 minutes, and then add dropwise to the reaction solution. 2 mL of NMP 2 (112 mg, 0.4 mmol) and TBAF (220 mg, 0.84 mg). After stirring for 10 minutes at room temperature, the temperature was raised to 70° C. and reacted for 5 hours. After cooling the reaction solution to room temperature, add 5 mL of saturated Na 2 S 2 O 3 The solution was stirred for 30 minutes. Extract with methyl tert-butyl ether (15 mL*5), co...

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 novel compound with a structure shown in the specification, wherein R is H, F or methoxyl. The novel compound is prepared by a method comprising the following steps: performing hydrosilylation by taking oxabenzonorbornadiene and dimethylphenylsilane as standard substrates and [Rh(COD)Cl]2 as a metal catalyst to obtain a product A; reacting the product A with tetrabutyl ammonium fluoride, cumyl hydroperoxide and potassium hydride to remove a silicon substrate so as to generate alcohol B; and reacting the alcohol B with benzyl bromide or benzyl chloride with different substituent groups under the action of alkali to obtain a target product. The invention further relates to a weeding composition comprising the novel compound, and also relates to an application of the novel compound particularly used for controlling weeds in useful plant crops.

Description

Technical field [0001] The invention belongs to the technical field of herbicides, and specifically relates to a novel compound and a preparation method and application thereof. Background technique [0002] Using oxabenzobornene and trichlorosilane as standard substrates, suitable catalysts for catalyzing the addition reaction were explored, and the application of chiral palladium catalysts in the asymmetric hydrosilation reaction was studied. Through research, we found that Pd(OAc) 2 The / (R)-MOP complex can smoothly catalyze the reaction to generate the target hydrosilation product. The hydrosilation product is processed by a hydrogen peroxide / sodium thiosulfate system to further oxidize and deprotect to generate a chiral alcohol. Analysis shows that the chiral alcohol derivative has an enantioselectivity of 70%, which indicates that the asymmetric hydrosilation product of oxabenzobornene compounds has an ee value of 70%, which is the result of asymmetric hydrosilation of such...

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): C07D493/08A01N43/90A01P13/00
CPCA01N43/90C07D493/08
Inventor 樊保敏徐歆周永云陈景超
Owner YUNNAN MINZU UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap