Polysubstituted cyclohexane and process for high selectively synthesizing polysubstituted cyclohexane by catalytic action of glyoxaline

A technology of cyclohexane and compound, applied in the field of synthesis of highly substituted cyclohexane, can solve the problem that the reaction is not reported in literature and the like, and achieve the effects of novel structure, high selectivity and efficient synthesis method

Inactive Publication Date: 2011-06-15
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] But there is no bibliographical report for the reaction that both nitrovinyl compound participates in and phthalonitrile olefin compound participates in

Method used

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  • Polysubstituted cyclohexane and process for high selectively synthesizing polysubstituted cyclohexane by catalytic action of glyoxaline
  • Polysubstituted cyclohexane and process for high selectively synthesizing polysubstituted cyclohexane by catalytic action of glyoxaline
  • Polysubstituted cyclohexane and process for high selectively synthesizing polysubstituted cyclohexane by catalytic action of glyoxaline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] In a reaction test tube equipped with a magnetic stirring bar, compound 1a (0.15 mmol), 2a (0.30 mmol) and imidazole (0.075 mmol) were added, and then 0.3 mL of tetrahydrofuran was added, and stirred at room temperature for 24 hours. After the reaction, the product 3a was obtained by flash column chromatography, and the eluent was (petroleum ether / ethyl acetate: 8:1-4:1).

[0046] Compound 3a.mp.214-215°C; IR(CH 2 Cl 2 )ν3066, 3037, 2982, 2942, 2883, 2244, 1562, 1497, 1458, 1366, 1299, 1004, 737, 701 cm -1 ; 1 H NMR (CDCl 3 , 300 MHz, TMS): δ 1.15 (3H, t, J=7.5 Hz, CH 3 ), 1.94-2.18 (2H, m, CH 2 ), 3.30 (1H, q, J = 4.5 Hz, CH), 3.56 (1H, s, CH), 4.00 (1H, d, J = 12.0 Hz, CH), 5.80 (1H, dd, J 1 = 4.5 Hz, J 2 =12.0 Hz, CH), 7.48-7.63 (8H, m, Ar), 7.82-7.85 (2H, m, Ar). 13 C NMR (CDCl 3 , 75 MHz): δ14.9, 20.4, 42.0, 45.1, 47.6, 48.0, 48.2, 81.4, 109.8, 111.2, 111.6, 112.2, 129.2, 129.3, 129.7, 130.2, 130.3, 130.7, 131.7.MS(EI)m / z 409(M + C 24 h 19 N 5 o 2 (...

Embodiment 2

[0048] In a reaction test tube equipped with a magnetic stirring bar, add compound 1a (0.15 mmol), 2b (0.30 mmol) and imidazole (0.075 mmol), and then add 0.3 mL of tetrahydrofuran, and stir at room temperature for 24 hours. After the reaction, the product 3b was obtained by flash column chromatography, and the eluent was (petroleum ether / ethyl acetate: 8:1-4:1).

[0049] Compound 3b.mp.204-205°C; IR(CH 2 CI 2 )ν 3052, 2978, 2940, 1664, 1567, 1479, 1367, 1265, 1079, 738 cm -1 ; 1 H NMR (CDCl 3 , 300 MHz, TMS): δ 1.14 (3H, t, J=7.2 Hz, CH 3 ), 1.92-2.11 (2H, m, CH 2 ), 3.33 (1H, q, J = 4.2 Hz, CH), 3.51 (1H, s, CH), 3.95 (1H, d, J = 12.0 Hz, CH), 5.73 (1H, dd, J 1 = 4.2 Hz, J 2 =12.0 Hz, CH), 7.37 (1H, t, J=8.1 Hz, Ar), 7.48 (2H, t, J=8.1Hz, Ar), 7.63-7.67 (2H, m, Ar), 7.74-7.78 ( 1H, m, Ar), 7.87-7.92 (2H, m, Ar). 13 C NMR (CDCl 3 , 75 MHz): δ14.8, 20.3, 41.7, 44.5, 46.9, 47.3, 48.0, 81.0, 109.3, 110.9, 111.1, 111.8, 123.7, 124.1, 127.1, 131.1, 131.2, 132.2, 132.3, 1...

Embodiment 3

[0051] In a reaction test tube equipped with a magnetic stirring bar, compound 1a (0.15 mmol), 2c (0.30 mmol) and imidazole (0.075 mmol) were added, and 0.3 mL of tetrahydrofuran was added, and stirred at room temperature for 24 hours. After the reaction, the product 3c was obtained by flash column chromatography, and the eluent was (petroleum ether / ethyl acetate: 8:1-4:1).

[0052] Compound 3c.mp.211-212°C; IR(CH 2 Cl 2 )ν 3067, 2979, 2942, 1660, 1592, 1566, 1493, 1417, 1365, 1079, 1011, 830, 740 cm -1 ; 1 H NMR (CDCl 3 , 300 MHz, TMS): δ 1.15 (3H, t, J=7.2 Hz, CH 3 ), 1.93-2.12 (2H, m, CH 2 ), 3.31 (1H, q, J = 4.5 Hz, CH), 3.51 (1H, s, CH), 3.96 (1H, d, J = 11.7 Hz, CH), 5.72 (1H, dd, J 1 = 3.9 Hz, J 2 =11.7 Hz, CH), 7.39 (2H, d, J=8.7 Hz, Ar), 7.64 (2H, t, J=8.7 Hz, Ar), 7.68-7.75 (4H, m, Ar). 13 C NMR (CDCl 3 , 75 MHz): δ 14.9, 20.3, 41.7, 44.6, 47.1, 47.5, 48.1, 109.5, 111.0, 111.4, 111.9, 125.4, 126.4, 128.0, 129.1, 130.7, 133.1, 133.6. MS(EI) m / z 569 (M + +2,...

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Abstract

The invention relates to high-substituted cyclohexane provided with a nitro-group and a nitrile group and a method for simply and conveniently synthesizing the same. The compound is provided with a structural formula shown as right, wherein, R1 group is phenyl, alkyl of C1-30, and alkyl phenyl of C1-30; R2 group is phenyl, phenyl of a mono or bis-substituted group, and a heterocyclic substituted group; the substituted group is alkyl of C1-4, alkoxyl of C1-4 or halogen; and the heterocyclic substituted group is indyl or pyridyl.

Description

technical field [0001] The present invention relates to a highly substituted cyclohexane compound having both nitro and nitrile groups, a synthesis method of the highly substituted cyclohexane with the above characteristics catalyzed by imidazole; the method is a 2+2+ catalyzed by imidazole 2 cycloaddition reactions, so as to obtain simple and efficient construction of multi-substituted cyclohexane. Background technique [0002] Organic synthesis reactions are the basis of organic synthetic chemistry, and its research has always been one of the most dynamic fields in organic chemistry. The total synthesis of complex natural products represented by the successful synthesis of sea anemone toxin (Kishi, Y. Chemica scripa 1987, 27, 573.) has made great progress and development in the second half of the 20th century, and the realization of these synthetic works Thanks to the establishment of some excellent synthetic methodologies to a large extent. In fact, for decades, organic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/46C07C253/30B01J31/02
Inventor 刘旭光施敏
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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