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Synthesis method of cyclobutanol nitro-substituted naphthol compound

A synthesis method and compound technology, applied in the preparation of nitro compounds, organic chemistry, etc., can solve the problems of a large number of by-products, low product yield, expensive reagents, etc., and achieve simple operation, high atom economy, and wide application range. Effect

Inactive Publication Date: 2019-02-22
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although this method is relatively reliable, there are still problems such as expensive reagents and low product yields.
On the other hand, naphthol compounds are mainly realized by methods such as the oxidation of naphthalene, which often require the use of strong oxidizing reagents and severe reaction conditions, and there are still problems such as poor reaction selectivity and a large number of by-products.

Method used

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  • Synthesis method of cyclobutanol nitro-substituted naphthol compound
  • Synthesis method of cyclobutanol nitro-substituted naphthol compound
  • Synthesis method of cyclobutanol nitro-substituted naphthol compound

Examples

Experimental program
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Effect test

Embodiment 1

[0014]

[0015] 1a (0.5mmol, 122mg), 2 (1.5mmol, 178μL) and acetonitrile (3mL) were sequentially added into a reaction tube, and the reaction was stirred at 50°C for 3h under an air atmosphere. Then the solvent was spin-dried and separated by silica gel column (petroleum ether / ethyl acetate=10 / 1) to obtain orange solid product 3a (77 mg, 50%). The characterization data of this compound are as follows: 1 H NMR (400MHz, CDCl 3 )δ:3.03(m,1H),3.80(d,J=14.8Hz,1H),3.86(d,J=14.4Hz,1H),7.28-7.34(m,3H),7.42-7.45(m,2H ),7.54-7.58(m,1H),7.61-7.68(m,2H),8.54(d,J=8.4Hz,1H),12.13(s,1H). 13 C NMR (100MHz, CDCl 3 )δ: 51.5, 81.1, 122.9, 125.2, 125.3, 125.9, 126.4, 126.7, 127.8, 128.6, 132.0, 132.2, 134.0, 136.2, 142.3, 156.9. HRMS calcd for C 18 h 13 NO 4 :306.0772[M-H] - ,found: 306.0775.

Embodiment 2

[0017] 1a (0.5mmol, 122mg), 2 (1.5mmol, 178μL) and toluene (3mL) were sequentially added into the reaction tube, and the reaction was stirred at 50°C for 3h under air atmosphere. Then the solvent was spin-dried and separated by silica gel column (petroleum ether / ethyl acetate=10 / 1) to obtain the orange solid product 3a (49 mg, 32%).

Embodiment 3

[0019] 1a (0.5mmol, 122mg), 2 (1.5mmol, 178μL) and 1,4-dioxane (3mL) were sequentially added into the reaction tube, and the reaction was stirred at 50°C for 3h under air atmosphere. Then the solvent was spin-dried and separated by silica gel column (petroleum ether / ethyl acetate=10 / 1) to obtain the orange solid product 3a (62 mg, 40%).

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Abstract

The invention discloses a synthesis method of a cyclobutanol nitro-substituted naphthol compound and belongs to the technical field of organic synthesis. The synthesis method of the cyclobutanol nitro-substituted naphthol compound is characterized by comprising the following steps of: dissolving orthoalkynyl substituted phenyl allenyl ketone compound and tert-butyl nitrite in a solvent, and heating in an air atmosphere for a temperature rise reaction to form the cyclobutanol nitro-substituted naphthol compound. The method has the advantages of easiness and simplicity in operation, mild conditions, wide substrate application scope and the like and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of cyclobutanol and nitro-substituted naphthol compounds. Background technique [0002] Cyclobutanol is an important class of organic compounds. First, cyclobutanol is an important building block of many bioactive molecules. Secondly, cyclobutanol is an important intermediate in organic synthesis, mainly because its four-membered rigid ring can undergo ring-opening, rearrangement and other reactions under mild reaction conditions to complete the recombination of carbon-carbon bonds, thereby generating different target molecule. On the other hand, naphthol is an important structural unit of many natural products, drugs and functional materials, and has important research value in the fields of natural product chemistry, medicinal chemistry, asymmetric synthesis and chemical biology. Cyclobutanol and nitro-substituted naphthol is a hybrid...

Claims

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Application Information

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IPC IPC(8): C07D333/16C07C201/06C07C205/25C07C205/37C07C205/26
CPCC07D333/16C07C201/06C07C2603/08C07C205/25C07C205/37C07C205/26
Inventor 范学森丰田何艳张新迎
Owner HENAN NORMAL UNIV
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