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Synthesis method of 3,4-dihydronaphthalene compound substituted by alkoxy

A synthesis method and compound technology, which can be used in the preparation of carbon-based compounds, the preparation of organic compounds, chemical instruments and methods, etc., can solve the problems of high cost, harsh reaction conditions, and low adaptability of reaction substrates.

Inactive Publication Date: 2019-05-21
HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The former is not very adaptable to the reaction substrate, while the latter needs to be carried out under an expensive catalytic system such as palladium / ligand, and the reaction conditions are relatively harsh. It is necessary to prepare alkenyl sulfonate reaction substrates in advance, and the cost is relatively high

Method used

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  • Synthesis method of 3,4-dihydronaphthalene compound substituted by alkoxy
  • Synthesis method of 3,4-dihydronaphthalene compound substituted by alkoxy
  • Synthesis method of 3,4-dihydronaphthalene compound substituted by alkoxy

Examples

Experimental program
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Effect test

Embodiment 1

[0051] Add methylenyl cyclopropane compound (0.2 mmol) shown in formula II-1 and oxone (chemical formula is KHSO 5 , 0.4 mmol, 2 equiv), followed by the addition of acetone (2 mL). Replace the air in the reactor with argon for 3-5 times, heat and react in an argon atmosphere at 90°C in an oil bath for 24 hours, check that the raw materials have reacted completely by TLC and / or GC-MS, and then filter the reaction solution , the organic phase was evaporated to dryness with a rotary evaporator, and the residue was separated and purified by column chromatography (eluent: petroleum ether / ethyl acetate, volume ratio 10:1) to obtain the target product shown in formula I-1. Yield 61%. yellow oily liquid; 1 H NMR (400 MHz, CDCl 3 ) δ: 7.45-7.37 (m, 4H), 7.35-7.31 (m, 1H), 7.06(t, J = 8.0 Hz, 1H), 6.81 (s, 1H), 6.76 (t, J = 7.6 Hz, 2H), 5.07 (s, 2H), 3.30 (s, 2H), 2.81 (t, J = 8.0 Hz, 2H), 2.24 (t, J = 8.0 Hz, 2H), 2.19 (s,3H); 13 C { 1 H}NMR (100 MHz, CDCl 3 ) δ: 207.0, 15...

Embodiment 2

[0053] Add the methylenecyclopropane compound (0.2 mmol), AgOTf (0.02 mmol, 10 mol %) and oxone (chemical formula KHSO 5 , 0.4 mmol, 2 equiv), followed by the addition of acetone (2 mL). Replace the air in the reactor with argon for 3-5 times, heat and react in an argon atmosphere at 90°C in an oil bath for 24 hours, check that the raw materials have reacted completely by TLC and / or GC-MS, and then filter the reaction solution , the organic phase was evaporated to dryness with a rotary evaporator, and the residue was separated and purified by column chromatography (eluent: petroleum ether / ethyl acetate, volume ratio 10:1) to obtain the target product shown in formula I-1. Yield 68%.

Embodiment 3

[0055] Consistent with Example 2, the only difference is that AgOAc is used instead of AgOTf. Yield 63%.

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Abstract

The invention discloses a synthesis method of a 2-(2-oxopropyl)-3,4-dihydronaphthalene compound and a 1-(3-oxobutyl)-3,4-dihydronaphthalene compound. The method includes the steps of sequentially adding a methenylcyclopropane derivative, a silver catalyst and an oxidizing agent in a formula II into a Schlenk sealed-tube reactor, then adding a ketone compound shown in a formula III, replacing air in the reactor with argon or nitrogen 3-5 times, and then heating the reactor for a reaction for 12-36 hours in an oil bath at 60-120 DEG C under the atmosphere of argon or nitrogen; after the reactionis completed, using a rotary evaporator for evaporating a solvent and separating and purifying residues through a chromatographic column to obtain a target product shown as a formula I.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a 3,4-dihydronaphthalene compound (2-(2-oxopropyl)-3,4-dihydronaphthalene compound and 1 -(3-oxobutyl)-3,4-dihydronaphthalene compound) synthetic method. Background technique [0002] 2-(2-oxopropyl)-3,4-dihydronaphthalene compounds and 1-(3-oxobutyl)-3,4-dihydronaphthalene compounds are very important organic synthesis intermediates For example, it can be used to synthesize antidepressant napamizole and its analogues. In the prior art, for 2-(2-oxopropyl)-3,4-dihydronaphthalene compounds and 1-(3-oxobutyl)-3,4-dihydronaphthalene compound synthesis strategies Less studied, representative schemes include the reaction of β-tetralone with diethyl acetylmethylphosphonate (see prior art (1) J. Med. Chem. 2001, 44, 787-805), and are constructed by the alkenylation of alkenyl sulfonate compounds with ketones (see prior art (2) Chem. Commun., 2017, 53, 952-955). The former...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/68C07C49/84C07C253/30C07C255/56C07C201/12C07C205/45C07C49/813C07C49/792C07D317/52
Inventor 刘宇王巧林陈赞熊碧权唐课文
Owner HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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