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2-sulfonyl-2,3-dihydro-1-indanone as well as derivative and synthesis method thereof

A kind of technology of derivatives, indanone, applied in the field of 2-sulfone-2, can solve problems such as large-scale production of unfavorable substances

Active Publication Date: 2021-03-30
HUNAN INSTITUTE OF ENGINEERING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are very few reports on the synthesis methods of 2-sulfone-2,3-dihydro-1-indanone compounds, and most of them need to be obtained by multi-step reactions catalyzed by transition metals, which is not conducive to the large-scale production of such substances , therefore, it is of great significance to develop an efficient and simple method for synthesizing such substances

Method used

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  • 2-sulfonyl-2,3-dihydro-1-indanone as well as derivative and synthesis method thereof
  • 2-sulfonyl-2,3-dihydro-1-indanone as well as derivative and synthesis method thereof
  • 2-sulfonyl-2,3-dihydro-1-indanone as well as derivative and synthesis method thereof

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Embodiment 1

[0066] The nuclear magnetic data of embodiment 1 product:

[0067] 1 H NMR (400MHz, CDCl 3 )δ7.93(d, J=7.7Hz, 2H), 7.74-7.53(m, 5H), 7.50(d, J=7.7Hz, 1H), 7.38(t, J=7.5Hz, 1H), 4.29( m, J=8.4, 3.4Hz, 1H), 3.83(d, J=18.3Hz, 1H), 3.55(m, J=18.3, 8.5Hz, 1H). 13 C NMR (100MHz, CDCl 3 )δ194.51, 151.87, 137.53, 135.99, 135.79, 134.28, 129.31, 129.12, 128.26, 126.45, 124.89, 77.39, 77.07, 76.76, 68.67, 28.12.

Embodiment 15

[0068] The nuclear magnetic data of embodiment 15 products:

[0069] 1 H NMR (400MHz, CDCl 3 )δ7.92(d, J=7.4Hz, 2H), 7.67(t, J=7.4Hz, 1H), 7.56(t, J=7.7Hz, 2H), 7.50(s, 1H), 7.44(d, J=7.9Hz, 1H), 7.37(d, J=7.9Hz, 1H), 4.29(m, J=8.4, 3.3Hz, 1H), 3.75(m, J=18.1, 2.5Hz, 1H), 3.48( m, J=18.1, 8.4Hz, 1H), 2.37(s, 3H). 13 C NMR (100MHz, CDCl 3 )δ194.53, 149.33, 138.38, 137.60, 137.31, 135.95, 134.23, 129.28, 129.10, 126.10, 124.71, 77.42, 77.10, 76.78, 68.98, 27.78, 21.07.

Embodiment 16

[0070] The nuclear magnetic data of embodiment 16 product:

[0071] 1 H NMR (400MHz, CDCl 3 )δ7.97-7.90 (m, 2H), 7.67 (t, J = 7.4Hz, 1H), 7.57 (t, J = 7.7Hz, 2H), 7.37-7.28 (m, 2H), 7.05 (d, J =7.7Hz, 1H), 4.28(m, J=8.3, 3.2Hz, 1H), 3.90(s, 3H), 3.71(m, J=18.6, 3.2Hz, 1H), 3.41(m, J=18.6, 8.3Hz, 1H). 13 C NMR (100MHz, CDCl 3 )δ194.66, 156.73, 140.91, 137.60, 137.17, 134.24, 129.88, 129.27, 129.12, 116.16, 116.06, 77.40, 77.09, 76.77, 68.57, 55.63, 25.17.

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Abstract

The invention mainly relates to 2-sulfonyl-2,3-dihydro-1-indanone and derivatives and a synthesis method thereof, under the combined action of an iodine-containing compound and an oxidizing agent, a 1indanone compound and sulfinate selectively generate a new CS bond at a carbonyl alpha site, and the 2-sulfonyl-2,3-dihydro-1-indanone compound is generated through a one-pot reaction. The product disclosed by the invention is stable in molecular structure and excellent in chemical property, and has potential biological activity and pharmacological activity; the method provided by the invention overcomes the defects that the existing synthesis method of the 2-sulfonyl-2,3-dihydro-1-indanone compound has complex synthesis steps and can be completed by adopting a multi-step synthesis process, sothat the atom economy is maintained to a great extent. The method also has the advantages of simple reaction system, mild reaction conditions, less reaction equipment, simple experimental operation,wide material sources, easy expansion of users and application, high product utilization value and the like.

Description

technical field [0001] The invention relates to 2-sulfone-2,3-dihydro-1-indanone and its derivatives and a synthesis method, belonging to the field of organic synthesis. Background technique [0002] Sulfone compounds are widely used in medicine, pesticides and other fields. Indanone compounds are important intermediate products in organic synthetic chemistry, which can be further transformed into other functional compounds. There are very few reports on the synthesis methods of 2-sulfone-2,3-dihydro-1-indanone compounds, and most of them need to be obtained by multi-step reactions catalyzed by transition metals, which is not conducive to the large-scale production of such substances Therefore, it is of great significance to develop an efficient and simple method for synthesizing such substances. Contents of the invention [0003] For above-mentioned situation, the object of the present invention is to provide a class of new compound namely 2-sulfone group-2,3-dihydro-1-i...

Claims

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Application Information

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IPC IPC(8): C07C315/00C07C317/24C07D213/71
CPCC07C315/00C07D213/71C07C2602/08C07C2601/02C07C317/24
Inventor 谢艳军易兵廖云峰阳海
Owner HUNAN INSTITUTE OF ENGINEERING