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Preparation method of allyl alcohol compound

A compound and allyl alcohol technology, applied in the field of preparing allyl alcohol compounds, can solve problems such as insufficient research, and achieve the effects of easy availability of raw materials, simple method operation and little impact

Pending Publication Date: 2022-06-07
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the photopromoted Cr / Ni-catalyzed NHK alkenylation of aldehydes to allyl alcohol is still understudied

Method used

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  • Preparation method of allyl alcohol compound
  • Preparation method of allyl alcohol compound
  • Preparation method of allyl alcohol compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]

[0032] Under nitrogen protection, to NiBr 2 (0.01mmol, 0.02eq), L 3 (0.011mmol, 0.022eq) and anhydrous CH 3 CrCl was added to CN(0.1M) solution 2 (0.1 mmol, 0.2 eq), HE (1.5 mmol, 3 eq), 1a (0.5 mmol, 1 eq) and 2a (1 mmol, 2 eq). The reaction mixture was stirred under 10W 400 nm LED irradiation for 48 hours at room temperature. After the reaction was completed, the solvent was evaporated in vacuo, and the crude product was purified by flash column chromatography (petroleum ether / ethyl acetate=5:1) to obtain compound 3a: a colorless oil in 76% yield (83 mg).

[0033] 1 H NMR (400MHz, CDCl 3 )δ7.29-7.25(m,2H),7.20-7.16(m,3H),5.67(dd,J=2.8,1.5Hz,1H),4.15(d,J=2.8Hz,2H),4.03(t , J=6.6Hz, 1H), 3.91-3.65(m, 2H), 2.81-2.51(m, 2H), 2.21-2.13(m, 1H), 2.11-2.02(m, 1H), 1.93-1.80(m , 3H). 13 C NMR (101MHz, CDCl 3 )δ141.75,137.80,128.37,128.35,125.82,121.43,74.48,65.15,64.17,36.18,31.81,24.02.HRMS:Calc’d for C 14 H 17 O,[M-OH] + 201.1274; found 201.1271.

Embodiment 2

[0035] With reference to the reaction conditions in Example 1, by changing different reaction substrates, the results are as follows:

[0036] Colorless oil in 61% yield (55 mg). 1 H NMR (400MHz, CDCl 3 )δ5.63(t,J=2.3Hz,1H),4.14(q,J=2.7Hz,2H),3.84(dt,J=10.6,5.1Hz,1H),3.76-3.71(m,2H), 2.25-2.17(m,1H),2.15-1.94(m,2H),1.81(dtd,J=12.2,7.4,4.6Hz,1H),1.72-1.46(m,6H),1.40(dq,J=13.0 ,8.1,7.6Hz,1H),1.32-1.08(m,1H). 13 C NMR (101MHz, CDCl 3 )δ137.75,122.22,80.31,65.14,64.31,43.11,29.24,29.17,25.65,25.54,23.87.HRMS:Calc’d for C 11 H 17 O,[M-OH] + 165.1274; found165.1272.

[0037] Colorless oil in 63% yield (62 mg). 1 H NMR (400MHz, CDCl 3)δ5.61(t,J=2.3Hz,1H),4.15(q,J=2.7Hz,2H),3.95-3.53(m,3H),2.18(dtt,J=16.7,4.4,2.2Hz,1H ),2.08-1.85(m,2H),1.84-1.58(m,4H),1.58-1.36(m,2H),1.34-1.05(m,3H),1.01-0.88(m,2H). 13 CNMR (101MHz, CDCl 3 )δ136.97,122.48,80.35,76.68,65.20,64.28,40.47,29.58,28.57,26.40,26.13,25.93,23.99.HRMS:Calc’d for C 12 H 19 O,[M-OH] + 179.1430; found179.1427. ...

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PUM

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Abstract

The invention discloses a preparation method of an allyl alcohol compound, and belongs to the field of organic chemistry. Aldehyde 1 and trifluoromethanesulfonic acid alkenyl ester 2 are used as raw materials, in the presence of a nickel / chromium catalyst, a phenanthroline or bipyridine ligand and a proton sacrificial agent, irradiation reaction is performed in an organic solvent, and an allyl alcohol compound 3 is obtained. According to the method, raw materials are easy to obtain, operation is easy, extra photocatalysts, metal reducing agents and additives are not needed, and it is proved that the method has very practical application value in complex molecule synthesis through drug molecule post-modification.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for preparing allyl alcohol compounds. Background technique [0002] Nozaki-Hiyama-Kishi (NHK) coupling, for the addition of vinyl-organochromium reagents to carbonyl compounds, has proven to be an efficient method for the construction of valuable allyl alcohols. Due to its excellent chemoselectivity and broad compatibility with functional groups, NHK reactions have been widely used in medicinal chemistry and total synthesis of natural products. [0003] However, light-promoted Cr / Ni-catalyzed NHK alkenylation of aldehydes to produce allyl alcohols remains understudied. SUMMARY OF THE INVENTION [0004] In order to overcome the above-mentioned technical defects, the object of the present invention is to provide a preparation method of allyl alcohol compounds. In the presence of nickel and chromium catalysts, aldehyde reacts with alkenyl trifluoromethanesu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/22C07F7/18C07D405/06C07D407/06C07D335/02C07D317/72C07D413/12C07D405/12C07C29/38C07C33/34C07C33/30
CPCC07D309/22C07F7/1804C07F7/1892C07D405/06C07D407/06C07D335/02C07D317/72C07D413/12C07D405/12C07C29/38C07C33/34C07C33/30C07C2601/10C07C2601/16Y02P20/55
Inventor 郝二军卢丙辉赵琰宋禹漫贾茹萍李桐崔杨波石磊
Owner HENAN NORMAL UNIV
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