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Stereospecific synthesized tetra-substituted olefin compound and novel method therefor

A tetra-substituted and alkene-based technology, which is applied in the field of stereospecific synthesis of tetra-substituted alkene compounds, can solve the problem of not being able to obtain tetra-substituted alkenes, and achieves the effects of high stereoselectivity, mild conditions and easy availability of reagents

Active Publication Date: 2016-05-04
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most existing methods for synthesizing four-substituted olefins with a single stereostructure have limitations, and generally all obtain a mixture of stereoisomers, but cannot obtain a single four-substituted olefin (Flynn, A.B.; Ogilvie, W.W.Chem.Rev.2007, 107, 4698-4745; Mori, M. Eur. J. Org. Chem. 2007, 4981-4993; Shindo, M.; Matsumoto, K. Top. Curr. Chem. 2012, 327, 1-32.; Paek, S.-M. Molecules 2012, 17, 3348-3358)

Method used

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  • Stereospecific synthesized tetra-substituted olefin compound and novel method therefor
  • Stereospecific synthesized tetra-substituted olefin compound and novel method therefor
  • Stereospecific synthesized tetra-substituted olefin compound and novel method therefor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1 (Z)-2, the synthesis of 3-diethyl-2-tetradecenal (001)

[0025]

[0026] Take a dry Schlenk reaction bottle and pump it under nitrogen three times. Under the protection of nitrogen, add 2-ethyl-2,3-tetradecadienal (0.2358g, 1.0mmol) and toluene (20mL) in turn to the reaction flask, add diethyl Zinc-based solution (1.2mL, 2.0Mintoluene, 2.4mmol), dripped within 4 minutes. The reaction was stirred at -10°C for 1 hour, then acetic acid (2 mL) was added dropwise by injection under stirring at -10°C, and the drop was completed within 2 minutes, and then returned to room temperature. After 20 minutes, add ethyl acetate (20mL), wash with dilute hydrochloric acid (20mL), saturated sodium bicarbonate solution (20mL), and saturated sodium chloride solution (20mL) successively, combine the aqueous phase, and wash the aqueous phase with diethyl ether (20mL× 2) Extract, combine the organic phases, dry over anhydrous sodium sulfate, filter, spin off the solvent and ...

Embodiment 2

[0027] Embodiment 2 (Z)-2, the synthesis of 3-diethyl-2-tridecenal (002)

[0028]

[0029] According to the method described in Example 1, the difference is that the substrates and reagents used are: 2-ethyl-2,3-tridecadienal (0.2221g, 1.0mmol), toluene (20mL), diethyl Zinc solution (1.6mL, 1.5Mintoluene, 2.4mmol) and acetic acid (2mL) gave (Z)-2,3-diethyl-2-tridecenal (0.2273g, 90%) (petroleum ether (30- 60°C) / ethyl acetate=100:1): liquid; 1 HNMR (300MHz, CDCl 3 )δ10.07(s, 1H, CHO), 2.53(t, J=7.8Hz, 2H, CH 2 ), 2.34-2.20 (m, 4H, CH 2 ×2), 1.57-1.42(m, 2H, CH 2 ), 1.41-1.19 (m, 14H, CH 2 ×7), 1.10(t, J=7.5Hz, 3H, CH 3 ), 0.94(t, J=7.7Hz, 3H, CH 3 ), 0.88(t, J=6.8Hz, 3H, CH 3 ); 13 CNMR (75MHz, CDCl 3 )δ191.2, 163.9, 137.7, 31.7, 30.7, 30.0, 29.6, 29.41, 29.39, 29.3, 29.2, 27.3, 22.5, 18.2, 13.9, 12.7; IR (neat) v (cm -1 ) 2961, 2926, 2855, 2752, 1669, 1618, 1464, 1376, 1336, 1287, 1251, 1155, 1060; MS (70ev, EI) m / z (%) 252 (M +, 30.82), 223(100); HRMScalcdforC ...

Embodiment 3

[0030] The synthesis of embodiment 3 (Z)-2-methyl-3-ethyl-2-tridecenal (003)

[0031]

[0032] According to the method described in Example 1, the difference is that the substrates and reagents used are: 2-methyl-2,3-tridecadienal (0.2076g, 1.0mmol), toluene (20mL), diethyl Zinc solution (1.6mL, 1.5Mintoluene, 2.4mmol) and acetic acid (2mL) gave (Z)-2-methyl-3-ethyl-2-tridecenal (0.2181g, 92%) (petroleum ether ( 30-60°C) / ethyl acetate=100:1): liquid; 1 HNMR (300MHz, CDCl 3 )δ10.09(s, 1H, CHO), 2.55(t, J=7.8Hz, 2H, CH 2 ), 2.28(q, J=7.5Hz, 2H, CH 2 ), 1.75 (s, 3H, CH 3 ), 1.58-1.41 (m, 2H, CH 2 ), 1.40-1.17 (m, 14H, CH 2 ×7), 1.08(t, J=7.7Hz, 3H, CH 3 ), 0.88(t, J=6.8Hz, 3H, CH 3 ); 13 CNMR (75MHz, CDCl 3 )δ191.4, 164.5, 131.6, 31.8, 30.5, 30.4, 29.6, 29.5, 29.4, 29.3, 29.2, 28.1, 22.6, 14.0, 11.9, 10.1; IR (neat) v (cm -1 ) 2957, 2925, 2855, 2752, 1671, 1623, 1467, 1396, 1377, 1325, 1282, 1156, 1029; MS (70ev, EI) m / z (%) 238 (M + , 27.08), 43(100); HRMScalcdfor...

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Abstract

The invention discloses a stereospecific synthesized tetra-substituted olefin compound and a novel method therefor. According to the method, the tetra-substituted olefin compound is synthesized in a high-regioselectivity and high-stereoselectivity manner through subjecting 2,3-biolefin aldehyde and an organic zinc reagent to a conjugate addition reaction and then carrying out further acid quenching. The method disclosed by the invention has the advantages that the operation is simple, raw materials and reagents are readily available, the reaction has high regioselectivity, high stereoselectivity and relatively good functional group compatibility, the product is easy to separate and purify, and the stereo-structured simple tetra-substituted olefin compound can be directly obtained.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a stereospecific synthesis of tetrasubstituted olefin compounds and a new method thereof. Background technique [0002] Compounds with a single stereostructure have a wide range of applications in life sciences, medicine, and chemistry. Among them, olefins with a single stereostructure are an indispensable class of compounds. It is well known that isomers with different configurations may have different physiological activities (Harper, M.J.K.; Walpole, A.L. Nature 1966, 212, 87). Most existing methods for synthesizing four-substituted olefins with a single stereostructure have limitations, and generally all obtain a mixture of stereoisomers, but cannot obtain a single four-substituted olefin (Flynn, A.B.; Ogilvie, W.W.Chem.Rev.2007, 107, 4698-4745; Mori, M. Eur. J. Org. Chem. 2007, 4981-4993; Shindo, M.; Matsumoto, K. Top. Curr. Chem. 2012, 327, 1-32.; P...

Claims

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Application Information

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IPC IPC(8): C07C45/69C07C47/21
CPCC07B2200/09C07C45/69C07C47/21
Inventor 麻生明戴健鑫傅春玲
Owner ZHEJIANG UNIV
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