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

Synthesis method of spiro hydroxyindolocyclopentane beta-exo fat compound

A technology of spirocyclic oxindole cyclopentane and synthesis method, which is applied in the field of synthesis of spirocyclic oxindole compounds, can solve problems such as being difficult to obtain, and achieves easy operation, excellent diastereoselectivity, and enantioselectivity. good effect of sex and diastereoselectivity

Active Publication Date: 2017-08-18
SUZHOU UNIV
View PDF1 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, the synthesis method of spiro-oxindole derivatives is relatively common, but the synthesis method of spiro-oxindole cyclopentane β-lactone compound has not been reported, because the stable cyclopentane β-lactone The lipid product is difficult to obtain, and the four-membered ring lactone is easy to open the ring to obtain the cyclopentene product after decarboxylation

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
  • Synthesis method of spiro hydroxyindolocyclopentane beta-exo fat compound
  • Synthesis method of spiro hydroxyindolocyclopentane beta-exo fat compound
  • Synthesis method of spiro hydroxyindolocyclopentane beta-exo fat compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]

[0030] The chemical structural formula of nitrogen heterocyclic carbene is as follows:

[0031]

[0032] Add nitrogen heterocyclic carbene (3.7 mg, 0.01 mmol) as a catalyst, and 1a (19.8 mg, 0.15 mmol), 2a (26 mg, 0.1 mmol), 4Å molecular sieves (10 mg) in sequence in the reaction flask, add 0.5 mL of Toluene was reacted at 0°C for 24 hours. The reaction system was subjected to simple column chromatography (eluent: ethyl acetate:petroleum ether=1:5) to obtain the target product 3a (21.1 mg) as a white solid. The rate was 54%, >99 / 1 dr, 91% ee; antibacterial drugs could be prepared.

[0033] Add nitrogen heterocyclic carbene (1.85 mg, 0.005 mmol) as a catalyst, and 1a (19.8 mg, 0.15 mmol), 2a (26 mg, 0.1 mmol), 4Å molecular sieves (5 mg) in turn into the reaction flask, add 0.5 mL mesitylene , reacted at 0°C for 24 hours, and the reaction system was subjected to simple column chromatography (eluent: ethyl acetate:petroleum ether=1:5) to obtain the target product ...

Embodiment 2

[0037]

[0038] Add nitrogen heterocyclic carbene (3.7 mg, 0.01 mmol) as a catalyst, and 1b (24.3 mg, 0.15 mmol), 2a (26 mg, 0.1 mmol), 4Å molecular sieves (10 mg) in sequence in the reaction flask, add 0.5 mL of Toluene was reacted at 0°C for 24 hours, and the reaction system was subjected to simple column chromatography (eluent: ethyl acetate: petroleum ether = 1:5) to obtain the target product 3b (23.9 mg) as a white solid. The rate was 57%, >99 / 1 dr, 91% ee, and antineoplastic drugs could be prepared.

[0039] Add nitrogen heterocyclic carbene (3.7 mg, 0.01 mmol) as a catalyst, and 1b (24.3 mg, 0.15 mmol), 2a (26 mg, 0.1 mmol) in sequence in the reaction flask, add 0.5 mL of mesitylene, at 0 °C After 24 hours of reaction, the reaction system was subjected to simple column chromatography (eluent: ethyl acetate:petroleum ether=1:5) to obtain the target product 3b (20.8 mg), a white solid, with a yield of 51%, >99 / 1 dr, 88% ee.

[0040] The product 3b was analyzed and t...

Embodiment 3

[0042]

[0043] Add nitrogen heterocyclic carbene (3.7 mg, 0.01 mmol) as a catalyst, 1b (26.5 mg, 0.15 mmol), 2a (26 mg, 0.1 mmol), 4Å molecular sieves (10 mg) in sequence, and add 0.5 mL of Toluene was reacted at 0°C for 24 hours. The reaction system was subjected to simple column chromatography (eluent: ethyl acetate:petroleum ether=1:10) to obtain the target product 3c (28.3 mg) as a white solid. The rate was 65%, >99 / 1 dr, 86% ee, and enzyme inhibitors could be prepared.

[0044] Add nitrogen heterocyclic carbene (3.7 mg, 0.01 mmol) as a catalyst, and 1b (26.5 mg, 0.15 mmol), 2a (26 mg, 0.1 mmol), 4Å molecular sieves (10 mg) in sequence in the reaction flask, add 0.5 mL tetrahydrofuran, After reacting at 0°C for 24 hours, the reaction system was subjected to simple column chromatography (eluent: ethyl acetate:petroleum ether=1:10) to obtain the target product 3c (20.6mg), a white solid, and the yield was 47%, >99 / 1 dr, 81% ee.

[0045] The product 3c was analyzed and ...

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 synthesis method of a spiro hydroxyindolocyclopentane beta-exo fat compound. The synthesis method comprises the following step: by taking phenyl unsaturated aldehyde and unsaturated ketoacid ester as reactants and by taking n-heterocyclic carbene as a catalyst, performing reaction, thus obtaining the spiro hydroxyindolocyclopentane beta-exo fat compound. According to the method disclosed by the invention, the raw materials are simple and readily available; the reaction conditions are mild; post-treatment is simple and convenient; the synthesis method is wide in application substrate range, high in yield and high in diastereoselectivity and enantioselectivity; therefore, a synthesized product can be used for synthesizing an intermediate of a medicine and a pesticide.

Description

technical field [0001] The invention relates to the synthesis of spiro-oxindole compounds, in particular to a catalytic synthesis method of spiro-oxindole cyclopentane and β-lactone compounds. Background technique [0002] Spiral oxindole compounds widely exist in natural products, and have significant physiological and pharmacological activities such as antiviral, bactericidal, enzyme activity inhibitory, antioxidative, antiradiative, and antitumor. At the same time, it is also an indispensable and important structural unit in many drug molecules, so it has attracted the attention of many scientists. The cyclopentane β-lactone compound also has good biological activity and medicinal value, but it is difficult to obtain because the product is prone to decarboxylation and leaves a molecule of carbon dioxide. Therefore, the development of efficient methods to combine these two types of structures with biological activity and pharmacological effects to synthesize chiral spiro-...

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): C07D491/107B01J31/02A61P31/00A61P35/00A61P31/18A61P31/12
CPCB01J31/0271C07D491/107
Inventor 王兴旺张俊琦
Owner SUZHOU 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