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A kind of preparation method of the compound containing isochroman-1-one skeleton

A chroman and compound technology, which is applied in the field of preparation of isochromanone skeleton-containing compounds, can solve the problems of long reaction time, cumbersome strong base reaction steps and the like, achieves simple reaction steps, improved yield, reduced effect of total cost

Active Publication Date: 2021-11-19
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods often involve the use of corrosive strong acids and strong bases or the reaction steps are cumbersome and the reaction time is long, so their application range is limited to a certain extent.

Method used

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  • A kind of preparation method of the compound containing isochroman-1-one skeleton
  • A kind of preparation method of the compound containing isochroman-1-one skeleton
  • A kind of preparation method of the compound containing isochroman-1-one skeleton

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1: Synthesis of 3-methyl-3-phenylisochroman-1-one

[0042] (1) Methyl o-iodobenzoate (0.037mL, 0.25mmol), α-methylstyrene (0.065mL, 0.5mmol), palladium acetate (0.0056g, 0.025mmol), three (2-methoxybenzene base) phosphine (0.0176g, 0.05mmol), silver carbonate (0.1379g, 0.5mmol), p-toluenesulfonic acid monohydrate (0.0048g, 0.025mmol), 1,1,1,3,3,3-hexafluoro - 2-propanol (0.5 mL), o-xylene (0.5 mL), stirred evenly in a clean and dry airtight reaction tube, heated to 130° C., and reacted for 24 hours.

[0043] (2) After the reaction is completed, cool the reaction tube to room temperature, add 30mL ethyl acetate to dilute the reaction system and transfer it to a 100mL separatory funnel, add 20mL saturated aqueous ammonium chloride solution, shake, let it stand, and remove the lower aqueous phase Afterwards, add 20mL of saturated saline again, shake, let stand, remove the lower aqueous phase, dry the organic phase with anhydrous sodium sulfate, remove the solvent ...

Embodiment 2

[0044] Example 2: Synthesis of 3,3-diphenylisochroman-1-one

[0045] (1) Methyl o-iodobenzoate (0.037mL, 0.25mmol), 1,1-stilbene (0.088mL, 0.50mmol), palladium acetate (0.0056g, 0.025mmol), three (4- trifluorotoluene base) phosphine (0.0233g, 0.05mmol), silver carbonate (0.1379g, 0.5mmol), p-toluenesulfonic acid monohydrate (0.0048g, 0.025mmol), 1,1,1,3,3,3-hexafluoro - 2-propanol (0.5 mL), o-xylene (0.5 mL), stirred evenly in a clean and dry airtight reaction tube, heated to 130° C., and reacted for 48 hours.

[0046] (2) After the reaction is completed, cool the reaction tube to room temperature, add 30mL ethyl acetate to dilute the reaction system and transfer it to a 100mL separatory funnel, add 20mL saturated aqueous ammonium chloride solution, shake, let it stand, and remove the lower aqueous phase Afterwards, add 20mL of saturated saline again, shake, let stand, remove the lower aqueous phase, dry the organic phase with anhydrous sodium sulfate, remove the solvent unde...

Embodiment 3

[0047] Example 3: Synthesis of 3-methyl-3-(p-tolyl)isochroman-1-one

[0048] (1) Methyl o-iodobenzoate (0.037mL, 0.25mmol), 1-methyl-4-(1-methylvinyl)benzene (0.073mL, 0.50mmol), palladium acetate (0.0056g, 0.025mmol ), tris(4-trifluoromethylphenyl)phosphine (0.0233g, 0.05mmol), silver carbonate (0.1379g, 0.5mmol), p-toluenesulfonic acid monohydrate (0.0048g, 0.025mmol), 1,1,1 , 3,3,3-hexafluoro-2-propanol (0.5mL), o-xylene (0.5mL), stirred evenly in a clean and dry airtight reaction tube, heated to 130°C, and reacted for 24 hours.

[0049] (2) After the reaction is completed, cool the reaction tube to room temperature, add 30mL ethyl acetate to dilute the reaction system and transfer it to a 100mL separatory funnel, add 20mL saturated aqueous ammonium chloride solution, shake, let it stand, and remove the lower aqueous phase Afterwards, add 20mL of saturated saline again, shake, let stand, remove the lower aqueous phase, dry the organic phase with anhydrous sodium sulfate, r...

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Abstract

The invention provides a method for preparing a compound containing isochroman-1-one skeleton, specifically methyl o-iodobenzoate substituted with substituents and 1, The 1-disubstituted olefin is used as a raw material, and a compound containing an isochroman-1-one skeleton is prepared through a cross-coupling reaction. The method does not use any directing group, and no additional steps are required to introduce or remove the directing group; the method has a wide range of functional groups and the tolerance of the functional group; the method has the advantages of cheap and easy-to-obtain raw materials, simple steps, and high overall yield of synthesis , The advantages of low total cost of synthesis. The prepared isochroman-1-one skeleton-containing compound has broad application prospects in the synthesis of pesticides, pharmaceutical intermediates, complex natural products, and the like.

Description

technical field [0001] The invention relates to a preparation method of a compound containing an isochromanone skeleton, in particular to a preparation method of a compound containing an isochromanone skeleton. [0002] technical background [0003] The isochroman-1-one skeleton structure has become the basic skeleton composition of many drug intermediates because of its antifungal, anticytotoxic, antimalarial, antiallergic and other activities, [see: (a) Chem.Pharm. Bull.1996,44,1440–1447; (b) J.Nat.Prod.2006,69,612–615.] Most of the compounds containing isochroman-1-one skeleton structure are derived from various It is isolated from natural products (such as plants, insects and microorganisms). In addition, there are also some reports on the preparation of compounds containing isochroman-1-one skeleton structures, which are currently commonly used to prepare The synthesis method of pyran-1-one skeleton structure compound includes: intermolecular ring closure reaction [see:...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/76
CPCC07D311/76
Inventor 文振康葛晓敏刘宇芳钞建宾
Owner SHANXI UNIV
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