Octachlorostyrene hapten, artificial antigen and specific antibody
A technology of octachlorostyrene and artificial antigen, applied in the detection field of octachlorostyrene
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Embodiment 1
[0062] Example 1: Synthesis of hapten intermediate (E)-1,2-dichloro-3-bromo-1-pentachlorophenyl-1-propene
[0063] (1) After dissolving pentachloronitrobenzene (10.3g, 34.88mmol) in ethyl acetate (25mL), add acetic acid-hydrochloric acid mixed acid solution (20mL) and iron powder (9.77g , 174.5mmol), reflux for 2h. Under cooling in an ice-water bath, the pH value of the reaction solution was adjusted to 10 with 2 mol / L NaOH solution, then suction filtered, and the filter cake was washed with ethyl acetate. The organic phase obtained by liquid separation was washed once with saturated NaCl solution, anhydrous NaCl 2 SO 4 dry. After filtration, the solvent was removed under reduced pressure to obtain 8.95 g of compound 2 as a white solid, with a yield of 97%.
[0064] (2) Under cooling in an ice-water bath, NaNO 2 (2.49g, 38.99mmol) was added to concentrated sulfuric acid solution (20mL) in portions. And at 0°C, the prepared NaNO 2 The solution was slowly added dropwise t...
Embodiment 2
[0068] Example 2: Synthesis of OCS Hapten Compound 1a
[0069] Compound 5 (150mg, 0.40mmol), succinic anhydride (44mg, 0.44mmol), and DMAP (49mg, 0.40mmol) were dissolved in dichloromethane (5mL), and reacted overnight at room temperature under nitrogen protection. After distilling off the solvent under reduced pressure, the residue was separated by silica gel column chromatography (dichloromethane first, then ethyl acetate) to obtain 119 mg of compound 1a as a white solid, with a yield of 63%.
[0070] Compound 1a: 1 H NMR (400MHz, actone-d 6 )δ:2.65~2.69(m,2H),2.72~2.72(m,2H),5.18(s,2H); 13 C NMR (100MHz, actone-d 6 )δ:28.99(CH 2 ), 29.27 (CH 2 ), 63.07 (CH 2 ), 125.60(C), 132.71(C), 132.84(C), 133.12(C), 135.80(C), 135.86(C), 172.15(C=O), 173.35(C=O); MS(EI) m / z:474.0(M + +2,2%),476.0(M + +4,2%).
Embodiment 3
[0071] Example 3: Synthesis of OCS Hapten Compound 1b
[0072] Compound 5 (176mg, 0.47mmol), fumaric acid (218mg, 1.88mmol), DMAP (6mg, 47μmol) was dissolved in DMF (1.5mL), and DCC (116mg, 0.56mmol) was added dropwise in dichloromethane solution (0.5 mL), react overnight at room temperature under nitrogen protection. After distilling off the solvent under reduced pressure, the residue was separated by silica gel column chromatography [V (petroleum ether): V (ethyl acetate): V (methanol) = 15:20:1] to obtain 129 mg of white solid compound 1b, the yield 58%.
[0073] Compound 1b: 1 H NMR (400MHz, actone-d 6 )δ:5.34(s,2H),6.89(d,J=0.80Hz,2H); 13 C NMR (100MHz, CDCl 3 )δ:63.82(CH 2 ),126.18(C),132.18(C),132.80(C),132.91(CH),133.22(C),135.69(C),135.86(CH),136.01(C),164.64(C=O),165.62 (C=O); MS(EI)m / z:469.8(M + ,4%),471.8(M + +2,11%),473.8(M + +4,10%),475.8(M + +6,5%).
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