Preparation method of 3,4-cyclopentyl-1-tetralone

A technology of tetralinone and cyclopentyl, which is applied in the field of preparation of 3,4-cyclopentyl-1-tetralinone, can solve rare problems and the like, achieves simple operation, excellent yield and good product selectivity Effect

Active Publication Date: 2016-09-14
ZHEJIANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] So far, the simple, efficient and economical synthesis of 3,4-cyclopentyl-1-tetralone is still very rare

Method used

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  • Preparation method of 3,4-cyclopentyl-1-tetralone
  • Preparation method of 3,4-cyclopentyl-1-tetralone
  • Preparation method of 3,4-cyclopentyl-1-tetralone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Take a dry Sri Lankan reaction tube, weigh into CuBr 2 (8.8mg, 0.040mmol), potassium carbonate (33.1mg, 0.24mmol), diethyl azodicarboxylate (13.9mg, 0.080mmol), and the ligand pentamethyldiethylenetriamine (13.8mg, 0.080 mmol), vacuumize and change nitrogen, replace three times, then add the raw material 2-vinylbenzaldehyde 1a (31.7mg, 0.24mmol) and 2-phenylallyl-2 bromopropanediol dissolved in 5mL dimethyl sulfoxide Acid diethyl ester 2a (70.8 mg, 0.20 mmol). After the reaction was stirred at room temperature for 12 h, it was quenched by adding 10 mL of water, extracted three times with ethyl acetate (10 mL), combined, the organic phase was washed with saturated edible water, and dried over anhydrous sodium sulfate. The organic phase was concentrated and separated by silica gel (300-400 mesh) column chromatography (eluent: petroleum ether / ethyl acetate volume ratio: 15 / 1) to obtain 65 mg of white solid product 3aa, yield 80%. The melting point of the product is 111-1...

Embodiment 2

[0032] Except that the alkenylbenzaldehyde shown in the structural formula 1a was used to replace the alkenylbenzaldehyde shown in the structural formula 1a in Example 1, the remaining operating steps were the same as in Example 1. The yield: 79%, a colorless liquid. 1 H NMR (600MHz, CDCl 3 ):δ7.49–7.45(m,1H),7.37–7.33(m,2H),7.30–7.23(m,2H),7.20–7.16(m,2H),7.14–7.10(m,1H),4.24 –4.13(m,4H),3.82(s,3H),3.79(d,J=11.6Hz,1H),3.55–3.48(m,1H),3.12–3.04(m,1H),2.92–2.85(m ,1H),2.60–2.53(m,1H),2.47–2.41(m,1H),2.30–2.24(m,1H),1.25(t,J=7.1Hz,3H),1.20(t,J=7.1 Hz,3H); 13 C NMR (151MHz, CDCl 3 ): δ197.5, 172.3, 172.2, 158.6, 138.2, 135.5, 132.5, 130.3, 129.5, 128.5, 127.0, 122.1, 109.6, 61.7, 59.5, 55.4, 54.7, 45.6, 41.6, 41.0, 38.0, 14.0; ESI) calcd for C 26 h 29 o 6 (M+H) + 437.1964, found 437.1956.

[0033] The reaction formula is as follows:

[0034]

Embodiment 3

[0036] Except that the alkenyl benzaldehyde shown in the structural formula 1c is used to replace the alkenyl benzaldehyde shown in the structural formula 1a in Example 1, the remaining operating steps are the same as in Example 1, the yield: 80%, white solid, melting point: 155-157 ° C ; 1 H NMR (600MHz, CDCl 3 ):δ7.44–7.40(m,1H),7.36–7.27(m,3H),7.19–7.15(m,2H),6.73(s,1H),6.01(s,2H),4.23–4.15(m ,4H),3.73(d,J=11.6Hz,1H),3.50–3.40(m,1H),3.07–2.99(m,1H),2.90–2.85(m,1H),2.58–2.51(m,1H ),2.44–2.38(m,1H),2.30–2.25(m,1H),1.25(t,J=7.0Hz,3H),1.22(t,J=7.1Hz,3H); 13 C NMR (151MHz, CDCl 3): δ195.8, 172.3, 172.1, 152.5, 147.3, 139.7, 138.4, 129.5, 128.5, 127.0, 126.5, 108.0, 106.6, 101.7, 61.7, 61.7, 59.3, 54.3, 45.6, 42.6, 40.9, 38.3 HR ESI) calcd for C 26 h 27 o 7 (M+H) + 451.1757,found 451.1753.

[0037] The reaction formula is as follows:

[0038]

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PUM

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Abstract

The invention discloses a preparation method of 3,4-cyclopentyl-1-tetralone; under a condition of the presence of a copper catalyst, a nitrogen ligand, a reducing agent and an alkali, alkenyl benzaldehyde and an alpha-brominated unsaturated carbonyl compound are stirred in a solvent and subjected to a reaction for 12 hours at room temperature, and the 3,4-cyclopentyl-1-tetralone is obtained after postprocessing. The method is simple to operate, mild in condition, good in functional group compatibility, wide in substrate applicability, high in yield and good in selectivity, and only needs one-step operation.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of 3,4-cyclopentyl-1-tetralone. Background technique [0002] Tetralones are very important pharmaceutical intermediates. 3,4-Cyclopentyl-1-tetralone, as a common class of tetralinone compounds, widely exists in nature, and many natural and non-natural molecules with physiological or pharmacological activities contain this fragment. Hamigeran natural products with various biological activities isolated from the secondary metabolites of marine sponges, such as hamigeran A, debromohamigeran A and hamigeran B, are all 3,4-cyclopentyl-1-tetralone compounds. [0003] [0004] Usually, the construction of the tricyclic compound structure in 3,4-cyclopentyl-1-tetralone requires multi-step synthesis, and the efficiency is not high. Building this structure through a single reaction can greatly reduce reaction steps, improve atom economy, and reduce en...

Claims

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Application Information

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IPC IPC(8): C07C69/757C07C67/313C07D317/70C07D333/24C07B37/10
CPCC07B37/10C07C67/313C07D317/70C07D333/24C07C69/757
Inventor 朱钢国朱慧罗芳黄倩雯
Owner ZHEJIANG NORMAL UNIVERSITY
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