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Synthesis method of alpha-nitrocycloalkanone

The technology of a nitrocycloalkanone and a synthesis method, which is applied in the field of organic intermediate synthesis, can solve the problems of no compound, expensive organotin compound and the like, and achieve the effect of simple reaction process

Active Publication Date: 2017-05-10
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although mercury acetate and lead acetate can be used to synthesize α-(4-tert-butylphenyl)α-nitrocyclohexanone, expensive and toxic organotin compounds are required, and there is only one case report. Compound method (WO2005087752 A2)

Method used

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  • Synthesis method of alpha-nitrocycloalkanone
  • Synthesis method of alpha-nitrocycloalkanone
  • Synthesis method of alpha-nitrocycloalkanone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Using 2-phenylcyclohexanone as raw material

[0020]

[0021] 2-Phenylcyclohexanone (34.8mg, 0.2mmol), cerium ammonium nitrate (330.0mg, 0.6mmol) and Cu(OAc) were sequentially added into a dry sealed 15mL tube 2 (16mg, 0.10mmol), then add 2.0mL DCE under argon atmosphere, seal with a lid, and react in an oil bath at 120°C for 12 hours. When the raw materials were consumed, the system was cooled to room temperature, then diluted with 5.0 mL of petroleum ether, and directly subjected to column chromatography (petroleum ether / ethyl acetate=40:1). A pale yellow solid (25.8 mg, yield 51.0%) was finally obtained.

[0022] The product detection data are as follows:

[0023] 1 H NMR (400MHz, CDCl 3 ):δ7.48-7.44(m,3H),7.36-7.33(m,2H),3.10-3.03(m,1H),2.92-2.86(m,1H),2.70-2.63(m,1H),2.59 -2.53(m,1H),1.97-1.87(m,3H),1.82-1.73(m,1H); 13 C NMR (100MHz, CDCl 3 ): δ200.5, 132.1, 130.2, 129.2, 128.4, 101.0, 40.2, 35.3, 27.3, 22.1.

Embodiment 2

[0025] Using 2-phenylcyclohexanone as raw material

[0026]

[0027] Add 2-phenylcyclohexanone (34.8mg, 0.2mmol), ammonium cerium nitrate (495.0mg, 0.9mmol) and CuSO 4 (6.4mg, 0.04mmol), then added 4.0mL DCE under argon atmosphere, sealed with a lid, and reacted in an oil bath at 120°C for 16 hours. When the raw materials were consumed, the system was cooled to room temperature, then diluted with 6.0 mL of petroleum ether, and directly subjected to column chromatography (petroleum ether / ethyl acetate=40:1). A pale yellow solid (20.1 mg, yield 46.0%) was finally obtained.

[0028] The spectral data of the product are the same as above.

Embodiment 3

[0030] Using 2-phenylcyclohexanone as raw material

[0031]

[0032] 2-Phenylcyclohexanone (34.8mg, 0.2mmol), cerium ammonium nitrate (495.0mg, 0.9mmol) and CuO (9.54mg, 0.06mmol) were successively added to a dry 15mL sealed tube, and then the Add 6.0mL DCE, seal with a lid, and react in an oil bath at 120°C for 10 hours. When the raw materials were consumed, the system was cooled to room temperature, then diluted with 6.0 mL of petroleum ether, and directly subjected to column chromatography (petroleum ether / ethyl acetate=40:1). A pale yellow solid (23.2 mg, yield 52.9%) was finally obtained.

[0033] The spectral data of the product are the same as above.

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Abstract

The invention discloses a synthesis method of alpha-nitrocycloalkanone. The structural formula of the alpha-nitrocycloalkanone is disclosed in the specification, wherein A is a five-ten-element ring, R is alkyl or aryl, and R' is hydrogen, alkyl, aryl or fused aryl. The method comprises the following step: under the catalytic action of a copper-base or iron-base catalyst, carrying out reaction on the compound disclosed in the specification and a nitrating agent to obtain the alpha-nitrocycloalkanone. By using the cheap copper-base or iron-base catalyst, the method can implement the synthesis of the alpha-nitrocycloalkanone economically and efficiently, and the reaction process is simple and safe and is easy to operate.

Description

technical field [0001] The invention belongs to the field of synthesis of organic intermediates, and in particular relates to a synthesis method of α-nitrocycloalkanone. Background technique [0002] α-phenyl-α-nitrocyclohexanone and its derivatives widely exist in active natural products and clinical drug molecules, and are also used as key building blocks in natural products (such as erythrina alkaloids) and drugs The synthesis of molecules. Moreover, α-phenyl-α-nitrocyclohexanone and its derivatives can be used as starting materials to synthesize chain compounds containing multifunctional groups by cutting carbon-carbon bonds. [0003] Although mercury acetate and lead acetate can be used for the synthesis of α-(4-tert-butylphenyl)α-nitrocyclohexanone, expensive and toxic organotin compounds are required, and there is only one case report. Compound method (WO2005087752 A2). Contents of the invention [0004] The technical problem to be solved by the present invention...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/34C07D209/34C07C201/08C07C205/45
CPCC07C201/08C07D209/34C07D311/34C07C205/45
Inventor 张辅民彭蕊张志强
Owner LANZHOU UNIVERSITY
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