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Method of synthesizing E-beta-bromo-gamma-hydroxymethylenesulphone

A technology of hydroxymethyl sulfone and allenyl sulfone, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., to achieve high regio and stereoselectivity and short reaction time

Inactive Publication Date: 2009-06-10
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] E-β-bromo-γ-hydroxymethyl sulfone is one of the most important intermediates in organic synthesis (H.Hiof, K.Natsuas LiebigsAnn.Chem.1988, 705.), and is also the most common structure in natural products One of the units (1.Krause, N.; Hashmi, A.S.K.Modern Allene Chemistry, Wiley-VCH, Weinheim, 2004.2S.Ma Chem.Rev.2005, 105, 2829.), has a variety of important physiological activities, in biological In the field of technology, medicine and pesticides have huge development and utilization value, and no literature has reported its synthesis method

Method used

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  • Method of synthesizing E-beta-bromo-gamma-hydroxymethylenesulphone
  • Method of synthesizing E-beta-bromo-gamma-hydroxymethylenesulphone

Examples

Experimental program
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Effect test

Embodiment 1

[0020] At room temperature, add 1-benzenesulfonyl-1,2-butadiene (58.5mg, 0.3mmol) into a 25mL single-necked bottle, add 3.3mL acetonitrile, stir to dissolve, slowly add 0.72mL (0.5 M acetonitrile solution, 0.36mmol) bromine in acetonitrile solution, stirred at 0°C for 30 minutes, added 6 mL of water, stirred at 0°C for another 30 minutes, extracted three times with ether, washed with saturated NaCl, dried over anhydrous sodium sulfate, concentrated the solution, Flash column chromatography gave 473.9 mg of the product E-3-bromo-4-benzenesulfonyl-3-buten-2-ol with a yield of 85%. The product is a white solid, melting point: 78-79°C (recrystallized from n-hexane and ether)

[0021] 1 H NMR (400 MHz, CDCl 3 )δ 7.91(d, J=8.4Hz, 2H), 7.67(t, J=8.0Hz, 1H), 7.58(t, J=8.0Hz, 2H), 6.78(s, 1H), 5.51(t, J =6.6Hz, 1H), 2.78(d, J=6.8Hz, 1H), 1.37(d, J=6.0Hz, 3H);

[0022] 13 C NMR (100 MHz, CDCl 3 )δ 150.6, 140.1, 134.1, 131.3, 129.6, 127.4, 65.4, 22.2;

[0023] MS (70cV, EI) m / z (%...

Embodiment 2

[0027] According to the method described in Example 1, the difference is that the substrates and reagents used are: 1-benzenesulfonyl-1,2-pentadiene (62.4mg, 0.3mol), bromine (0.5M acetonitrile solution, 0.72mL) , 6 mL of water was reacted at room temperature to obtain 62.0 mg of product E-2-bromo-1-benzenesulfonyl-1-penten-3-ol with a yield of 68%. The product is a colorless liquid.

[0028] 1 H NMR δ 7.91(d, J=6.8Hz, 2H), 7.66(t, J=8.0Hz, 1H), 7.57(t, J=6.8Hz, 2H), 6.83(s, 1H), 5.33(t, J=6.8Hz, 1H), 2.74(s, 1H), 1.71-1.78(m, 1H), 1.57-1.66(m, 1H), 0.93(t, J=7.4Hz, 3H);

[0029] 13 C NMR (100 MHz, CDCl 3 )δ 149.5, 140.3, 134.1, 132.5, 129.6, 127.5, 70.2, 29.1, 9.4;

[0030] MS (70 eV, EI) m / z (%): 307 (M + ( 81 Br), 0.04), 305 (M + ( 79 Br), 0.11), 125(100),

[0031] IR(neat)v(cm -1 )3487, 3043, 1601, 1447, 1310, 1115;

[0032] HRMS Calcd for C 11 h 12 BrO 3 S(M + -H): 304.9670( 81 Br), 302.9682 ( 79 Br), Found: 304.9677 ( 81 Br), 302.9682 ( 79 Br).

Embodiment 3

[0034] According to the method described in Example 1, the difference is that the substrates and reagents used are: 1-benzenesulfonyl-1,2-hexadiene (66.3mg, 0.30mmol), bromine (0.5M acetonitrile solution, 0.9mL) , 6 mL of water was reacted at room temperature to obtain 57.2 mg of product E-2-bromo-1-benzenesulfonyl-1-hexen-3-ol with a yield of 60%. The product is a colorless liquid.

[0035] 1 H NMR (400 MHz, CDCl 3 )δ 7.91(d, J=8.4Hz, 2H), 7.66(t, J=7.2Hz, 1H), 7.57(t, J=7.2Hz, 2H), 6.80(s, 1H), 5.40(t, J =6.2Hz, 1H), 2.74(s, 1H), 1.66-1.74(m, 1H), 1.41-1.59(m, 2H), 1.24-1.34(m, 1H), 0.93(t, J=7.2Hz, 3H);

[0036] 13 C NMR (100 MHz, CDCl 3 )δ 149.9, 140.2, 134.0, 131.9, 129.5, 127.4, 68.7, 37.9, 18.2, 13.7;

[0037] MS (70eV, EI) m / z (%): 303 (M + ( 81 Br)-17, 0.73), 301 (M + ( 79 Br)-17, 0.83), 77(100);

[0038] IR(KBr)v(cm -1 )3492, 3044, 1604, 1309, 1152;

[0039] HRMS Calcd for C 12 h 15 79BrO 3 S(M + ): 317.9925, Found: 317.9938.

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Abstract

The invention discloses a synthesizing method of E-beta-bromine-gamma-hydroxy methylene sulfone with high area and cubic selectivity, which is characterized by the following: reacting olefin sulfone and electrophilic reaction high-area cubically and selectively; obtaining the product with simple operation and easy raw material and agent; separating and purifying easily; fitting for synthesizing each kind of substituted E-beta-bromine-gamma-hydroxy methylene sulfone.

Description

technical field [0001] The present invention relates to a method for synthesizing E-β-bromo-γ-hydroxymethylene sulfone with high regio- and stereoselectivity, that is, through the electrophilic reaction of allenyl sulfone with bromine with high regio- and stereoselectivity Method for synthesizing E-β-bromo-γ-hydroxymethylsulfone. Background technique [0002] E-β-bromo-γ-hydroxymethyl sulfone is one of the most important intermediates in organic synthesis (H.Hiof, K.Natsuas LiebigsAnn.Chem.1988, 705.), and is also the most common structure in natural products One of the units (1.Krause, N.; Hashmi, A.S.K.Modern Allene Chemistry, Wiley-VCH, Weinheim, 2004.2S.Ma Chem.Rev.2005, 105, 2829.), has a variety of important physiological activities, in biological In the field of technology, it has huge development and utilization value in medicine and pesticides, and there is no literature report on its synthesis method. Contents of the invention [0003] The object of the present...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C317/22C07C315/04
Inventor 麻生明周超傅春玲
Owner ZHEJIANG UNIV
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