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

A kind of synthetic method of novel chiral nitrobinaphthol and its derivatives

A technology of nitrobinaphthol and synthesis method, which is applied in the field of organic synthesis, can solve the problems of many by-products, pollute the environment, and low atom economy, and achieve the effect of less reaction by-products and mild conditions

Active Publication Date: 2020-11-27
QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
View PDF2 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has mature technology and low cost, but low atom economy, serious environmental pollution and many by-products

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
  • A kind of synthetic method of novel chiral nitrobinaphthol and its derivatives
  • A kind of synthetic method of novel chiral nitrobinaphthol and its derivatives
  • A kind of synthetic method of novel chiral nitrobinaphthol and its derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: the target product in the present embodiment is:

[0029] Specifically, it is realized by the following steps:

[0030] Add 1mmol (R)-1,1'-binaphthol into the reaction flask, dissolve it in 5mL tetrahydrofuran, add 422uL tert-butyl nitrite, stir at room temperature, and react for 12 hours. After the reaction, use rotary evaporation The organic solvent was removed, and the product nitrobinaphthol was obtained by column chromatography, and the reaction yield was 92%.

Embodiment 2

[0031] Embodiment 2: the target product in the present embodiment is:

[0032] Specifically, it is realized by the following steps:

[0033] Add 1mmol (R)-1,1'-binaphthol into the reaction flask, dissolve it in 5mL tetrahydrofuran, add 422uL tert-butyl nitrite, stir at room temperature, and react for 12 hours. After the reaction, use rotary evaporation The organic solvent was removed by using an instrument, and the product nitrobinaphthol was obtained by column chromatography, and the reaction yield was 95%.

Embodiment 3

[0034] Embodiment 3: the target product in the present embodiment is:

[0035] Specifically, it is realized by the following steps:

[0036] Add 1mmol (R)-1,1'-binaphthol into the reaction flask, dissolve it in 2mL tetrahydrofuran, add 422uL tert-butyl nitrite, stir at room temperature, and react for 12 hours. After the reaction, use rotary evaporation The organic solvent was removed, and the product nitrobinaphthol was obtained by column chromatography, and the reaction yield was 93%.

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 relates to a synthesizing method of novel chiral nitro binaphthol and derivatives thereof, and belongs to the field of organic synthesis. A novel green free radical nitrifying method isprovided, and comprises the following steps of using chiral binaphthol as the raw material, and generating free radical nitrifying reaction with a green nitrifying reagent (TBN (tert-butyl nitrite)) at room temperature by using tetrahydrofuran as a reaction solvent, so as to obtain the chiral nitro binaphthol. The synthesizing method has the advantages that the metal is not used in reaction, and the TBN is directly used in the nitrifying reaction; only the product and tertiary butanol are generated in reaction, and the pollution to environment is reduced; the important application prospect isrealized in the synthesizing field of the chiral nitro binaphthol, the green nitrifying is truly realized, and a novel concept is provided for the large-scale industrialized production of the nitro binaphthol.

Description

technical field [0001] The invention relates to a method for preparing novel chiral nitrobinaphthol and derivatives thereof, in particular to a method for preparing chiral phosphoric acid and chiral phosphorus ligands, and belongs to the field of organic synthesis. Background technique [0002] In 1873, Von Richter first reported the synthesis of the racemate of binaphthol (BINOL) (structural formula 1). However, it was not until the 1970s that chiral BINOL was prepared and its absolute configuration determined. The two naphthalene rings in the binaphthol structure are bulky, so the steric hindrance is large and rigid, and because of the coaxial effect between the two rings, there is still room for rotation and flexibility. Chiral binaphthol and its derivatives have strong chiral induction, and have been widely used in asymmetric alkylation of aldehydes, asymmetric reduction of ketones, asymmetric Mannich reactions, asymmetric MBH reactions, asymmetric Many important organ...

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): C07C201/08C07C205/25C07C205/26C07C205/22
CPCC07B2200/07C07C201/08C07C2602/10C07C2603/24C07C2603/97C07C205/25C07C205/26C07C205/22
Inventor 王庆刚徐广强咸漠吕承东
Owner QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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