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A kind of synthetic method of nine-membered ring compound

A synthesis method and compound technology, applied in the direction of organic chemistry, etc., can solve the problems of difficult and rare middle-ring compounds

Active Publication Date: 2021-11-09
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The commonly used synthesis methods of mesocyclic compounds mainly include intramolecular cyclization, ring expansion reaction, etc., but it is more difficult to construct mesocyclic compounds through intermolecular reactions. Currently, there are few reports on the successful preparation of mesocyclic compounds using simple and easy-to-obtain raw materials

Method used

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  • A kind of synthetic method of nine-membered ring compound
  • A kind of synthetic method of nine-membered ring compound
  • A kind of synthetic method of nine-membered ring compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] PD 2 (dba) 3 Complexation with L-1-1 as a catalyst catalyzes the reaction to generate (Z)-2,11-di-tert-butyl-6-(thienyl-2-methylene)-6,7-dihydrobenzo[e ,h][1,4,7]dioxathionine 13-oxide Ⅰ-1.

[0057] Add the metal precursor Pd in ​​the reaction flask 2 (dba) 3 (0.005mmol, 5mol%) and chiral ligand L-1-1 (0.011mmol, 5.5mol%), added 1.0mL anhydrous tetrahydrofuran under nitrogen protection, and stirred at room temperature for 1 hour. Then propargyl alcohol ester Ⅳ-1 (0.24mmol, 1.2equiv), 2,2'-sulfinyl diphenol compound Ⅲ-1 (0.2mmol, 1.0equiv) and Cs 2 CO 3 (0.24mmol, 1.2equiv) was dissolved in 2.0mL of anhydrous tetrahydrofuran, and then the solution was added to the above stirred catalyst solution under the protection of nitrogen, and the reaction was stirred at room temperature for 24h. After the reaction was completed, it was concentrated under reduced pressure to almost no solvent, separated by silica gel column chromatography, concentrated under reduced pressure,...

Embodiment 2

[0062] L-2-1 acts as a ligand to generate product Ⅰ-1

[0063] The ligand L-1-1 in Example 1 is replaced by the ligand L-2-1, and the rest are the same as in Example 1. The reaction yielded compound I-1 with a yield of 15% and configuration ratio Z / E=17:1.

[0064] The structural formula of L-2-1 is as follows:

[0065]

Embodiment 3

[0067] L-2-2 acts as a ligand to generate product Ⅰ-1

[0068] The ligand L-1-1 in Example 1 is replaced by the ligand L-2-2, and the rest are the same as in Example 1. The reaction yielded compound I-1 with a yield of 98%, and the configuration ratio Z / E>25:1.

[0069] The structural formula of L-2-2 is as follows:

[0070]

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Abstract

The invention provides a method for synthesizing a nine-membered ring compound, specifically a method for synthesizing a nine-membered ring compound from 2,2'-sulfinyl diphenol and a propargyl compound through a [7+2] cycloaddition reaction using a palladium catalyst system. Methods for membered rings. The palladium catalyst used is generated in situ by palladium salt and 1,1'-bis(diphenylphosphino)ferrocene in various polar and nonpolar solvents. The present invention can conveniently synthesize various functionalized 6-methylene-6,7-dihydrobenzo[e,h][1,4,7]dioxathionine 13-oxide nine-membered rings Compound, its yield is as high as 99%. The invention has the characteristics of simple operation, readily available raw materials, wide application range of substrates, high reactivity and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of a nine-membered ring compound. Background technique [0002] Middle ring compounds widely exist in nature, and many derivatives have important biological activity and pharmacological value. Therefore, the synthesis of such compounds has been widely concerned by scientific researchers, and it is also one of the difficulties in the field of organic synthesis. Due to the mismatch in thermodynamics and kinetics, as well as the unique cross-ring interaction of mesocyclic compounds, the synthesis of mesocyclic compounds is often restricted by the more stable small ring by-products in the reaction process. The commonly used synthetic methods of mesocyclic compounds mainly include intramolecular cyclization and ring expansion reaction, etc., but it is more difficult to construct mesocyclic compounds through intermolecular reactions. Currently, there are...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D327/10C07D411/06
Inventor 胡向平刘振婷
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI