Supercharge Your Innovation With Domain-Expert AI Agents!

Double functional group L-proline derivative with adjustable catalytic activity and its prepn

A technology of proline and derivatives, which is applied in the field of preparation of bifunctional L-proline derivatives, can solve the problems of general selectivity and achieve good catalytic activity

Inactive Publication Date: 2008-01-16
HUAZHONG NORMAL UNIV
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most catalytic systems only have good catalytic activity for more active aldol donors such as acetone; while for other less active donors such as cyclohexanone, cyclopentanone, etc., the selectivity is average.

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
  • Double functional group L-proline derivative with adjustable catalytic activity and its prepn
  • Double functional group L-proline derivative with adjustable catalytic activity and its prepn
  • Double functional group L-proline derivative with adjustable catalytic activity and its prepn

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Preparation

[0018] Under the protection of room temperature and dry nitrogen, 3.42 g (30 mmol) (1R, 2R)-diaminocyclohexane was dissolved in 20 mL of dichloromethane solution, and the mixture was cooled to 0° C. and stirred vigorously. Dissolve 10mmol of 4-methylbenzoyl chloride in 10mL of dichloromethane and add it dropwise to the reaction system: After the addition is completed, warm to room temperature and react for 12 hours; after the reaction, the solvent is evaporated, and the residue is added dropwise to the silica gel column , And perform column chromatography separation with ethyl acetate / methanol, the volume ratio of ethyl acetate to methanol is 3:1, and the chromatographic liquid is removed under reduced pressure to obtain the amide intermediate.

[0019] Dissolve 2.15g (10mmol) of Boc-protected L-proline and 2.07g (10mmol) of N,N'-dicyclohexylcarbimide in 20mL of dichloromethane and vigorously stir at 0°C for 30 minutes. 1.86g (8mmol) of amide intermediate in...

Embodiment 2

[0026] Preparation

[0027] Under the protection of room temperature and dry nitrogen, 3.42 g (30 mmol) (1R, 2R)-diaminocyclohexane III was dissolved in 20 mL of dichloromethane solution, and cooled to 0° C. and stirred vigorously. Dissolve 10mmol of 4-chlorobenzoyl chloride in 10mL of dichloromethane and add it dropwise to the reaction system; after the dropwise addition is completed, warm to room temperature and react for 12 hours; after the reaction, the solvent is evaporated, and the residue is carried out with ethyl acetate / methanol Column chromatography separation (the method is the same as in Example 1) to obtain the amide intermediate.

[0028] Dissolve 2.15g (10mmol) of Boc-protected L-proline and 2.07g (10mmol) of N,N'-dicyclohexylcarbimide in 20mL of dichloromethane and vigorously stir at 0°C for 30 minutes. 10 mL of a dichloromethane solution of 2.02 g (8 mmol) of the amide intermediate was added dropwise to the reaction system. After the dropwise addition, it was ra...

Embodiment 3

[0035] Preparation

[0036] Under the protection of room temperature and dry nitrogen, 3.42 g (30 mmol) (1R, 2R)-diaminocyclohexane was dissolved in 20 mL of dichloromethane solution, and cooled to 0° C. and stirred vigorously. 10mmol of trifluoroacetyl chloride was dissolved in 10mL of dichloromethane and added dropwise to the reaction system. After the addition, the temperature was raised to room temperature and reacted for 12 hours. After the reaction, the solvent was evaporated, and the residue was subjected to column chromatography with ethyl acetate / methanol (the method is the same as in Example 1) to obtain the amide intermediate.

[0037]Dissolve 2.15g (10mmol) Boc-protected L-proline and 2.07g (10mmol) N,N'-dicyclohexylcarbimide in 20mL dichloromethane and stir vigorously for 30 minutes at 0°C. 10 mL of a dichloromethane solution of 1.68 g (8 mmol) of the amide intermediate was added dropwise to the reaction system. After the addition, the temperature was raised to room...

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

PropertyMeasurementUnit
diameteraaaaaaaaaa
Login to View More

Abstract

The present invention is one kind of double functional group L-proline derivatives with adjustable catalytic activity and their preparation process. The general expression of the L-proline derivatives is shown. The compounds have excellent catalytic activity on asymmetrical hydroxyaldehyde reaction and may be used as high selectivity organic catalyst.

Description

Technical field [0001] The invention relates to the preparation of an adjustable bifunctional L-proline derivative and its application as an organic catalyst in asymmetric direct aldol reaction. Background technique [0002] In 1974, Wiechert, Hajos, and Parrish first reported on organocatalytic reactions with corresponding selectivity. However, in the nearly thirty years after the second, metal catalysis has always been dominant in the field of asymmetric catalysis. Until recently, asymmetric catalysis has gradually attracted people's interest and has become a research hotspot. The organic catalysis has simple operation, mild reaction conditions and easy preparation, and has obvious industrial application prospects. [0003] Asymmetric aldol reaction is one of the important methods to construct complex polyhydroxy compounds. Since List and Barbas first reported the direct aldol reaction catalyzed by L-proline, various L-proline derivatives catalyzed the aldol reaction have been ...

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 Patents(China)
IPC IPC(8): C07D207/16B01J31/02C07B53/00
Inventor 肖文精陈加荣陆海华李新勇
Owner HUAZHONG NORMAL UNIV
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com