Method for synthesizing alpha-1,3-dithiane substituted aldehyde compound

A technology of aldehyde compounds and dithiane, which is applied in the field of synthesizing α-1,3-dithiane substituted aldehyde compounds, can solve the problems of large environmental pollution, low reaction yield, and high toxicity of Lewis acid

Inactive Publication Date: 2017-09-12
LANZHOU UNIVERSITY
View PDF2 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But these methods use the bigger Lewis acid of toxicity, bigger to environmental pollution; Due to the higher activity of nucleophilic silan

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 synthesizing alpha-1,3-dithiane substituted aldehyde compound
  • Method for synthesizing alpha-1,3-dithiane substituted aldehyde compound
  • Method for synthesizing alpha-1,3-dithiane substituted aldehyde compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018]

[0019] In a 10 ml round bottom flask, add 1,3-dithiane 2 (24 mg, 0.2 mmol), dissolve it with 2 ml of 1,2-dichloroethane and add N-chlorosuccinimide (29 mg, 0.22mmol), then add CuCl 2 (5mol%), 1a (17mg, 0.3mmol), stirred at room temperature for 1~1.5h. TLC detected that the reaction was stopped after the reaction was complete, and the product 3a was obtained by column chromatography after the solvent was evaporated. The resulting product data are characterized as follows:

[0020] Colorless oil, yield: 85%, R f =0.34 (EA / PE=1:10). 1 H NMR (300MHz, CDCl 3 )δ9.70(d,J=1.7Hz,1H), 4.41(d,J=5.8Hz,1H),3.05–2.80(m,4H),2.79–2.66(m,1H),2.24–1.77(m ,2H),1.27(d,J=7.1Hz,3H). 13 C NMR (75MHz, CDCl 3 )δ201.1,50.2,48.0,30.1,30.0,25.3,11.3.IR(neat,cm -1 )3052(w),2935(m),2904(m),2830(m),2727(w),1724(s),1670(w),1423(m),1375(w),1266(w) ,1185(w),946(w),908(m),736(s), 703(m),658(w).HRMS(ESI):m / z:calcd for C 7 h 13 OS 2 [M+H] + :177.0408,found:177.0405

Embodiment 2

[0022]

[0023] In a 10 ml round bottom flask, add 1,3-dithiane 2 (24 mg, 0.2 mmol), dissolve it with 2 ml of 1,2-dichloroethane and add N-chlorosuccinimide (29 mg, 0.22mmol), then add CuCl 2 (5mol%), 1a' (22mg, 0.3mmol), stirred and reacted at room temperature for 1~2h. TLC detected that the reaction was stopped after the reaction was complete, and the product 3a was obtained by column chromatography after the solvent was evaporated. The resulting product data are characterized as follows:

[0024] Colorless oil, yield: 80%, R f =0.34 (EA / PE=1:10).

Embodiment 3

[0026]

[0027] In a 10 ml round bottom flask, add 1,3-dithiane 2 (24 mg, 0.2 mmol), dissolve it with 2 ml of 1,2-dichloroethane and add N-chlorosuccinimide (29 mg, 0.22mmol), then add CuCl 2 (5mol%), 1a" (30mg, 0.3mmol), stirred and reacted at room temperature for 1-2h. TLC detection stopped the reaction after the reaction was complete, evaporated the solvent and obtained product 3a by column chromatography. The data of the obtained product were characterized as follows:

[0028] Colorless oil, yield: 75%, R f =0.34 (EA / PE=1:10).

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 method for synthesizing alpha-1,3-dithiane substituted aldehyde compound. The preparation method comprises the following steps: under existence of an activating agent of N-chloro succinimide and a catalyst of Cu(II), dissolving 1,3-dithiane and substituted vinyl ether into an organic solvent, reacting for 1 to 4 hours under room temperature to 50 DEG C and separating and purifying to obtain alpha-1,3-dithiane substituted aldehyde compound. The method disclosed by the invention has moderate operation condition and avoids rigorous dewatering operation and device, the utilized commercialized vinyl ether compound is cheap and easy to obtain, a reaction process is simple, good functional group tolerance is obtained, a beneficial technological effect is obtained, and the method can be well applied to scientific researches and industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing α-1,3-dithiane substituted aldehyde compounds Background technique [0002] The α-1,3-dithiane substituted aldehyde compound is an important intermediate for the construction of heterocyclic, polycarbonyl and other drug molecules and natural products. Its structure has both carbonyl and thiane functional groups. The thiane group can be As a carbonyl equivalent, a series of functional group conversions are used for the construction of complex organic molecular skeletons and fragments; while aldehyde groups can participate in the conversion of many functional groups and the construction of complex heterocycles, such as the rapid conversion of substituted 1,3-dialdehyde compounds , and hydrazine hydrate, phenylhydrazine cyclization synthesis of pyrazole compounds. The traditional method is through the selective monoprotection of dialdehyde compounds, but the selectivity is poor and the yield is low. The...

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
IPC IPC(8): C07D339/08
CPCC07D339/08
Inventor 唐寿初闵灯刘腾袁昕钰
Owner LANZHOU UNIVERSITY
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