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A kind of preparation of high allyl alcohol compound and its synthesis method and application

A technology of high allyl alcohol and synthesis method, applied in the directions of steroids, organic chemical methods, chemical instruments and methods, etc., can solve problems such as uneconomical, cumbersome methods, etc., and achieve high selectivity, high reaction yield, and short step effect

Active Publication Date: 2021-07-13
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the tedious and uneconomical preparation method, which relies on preactivated allyl halides and stoichiometric metal reducing agents, limits its application.

Method used

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  • A kind of preparation of high allyl alcohol compound and its synthesis method and application
  • A kind of preparation of high allyl alcohol compound and its synthesis method and application
  • A kind of preparation of high allyl alcohol compound and its synthesis method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]

[0033] The experimental steps and purification methods were carried out according to the exploratory experiments. RF=0.4 (EA:PE=1:3), eluent: petroleum ether / ethyl acetate=20 / 1, the yield was 92%, and the product was a colorless liquid. 1 H NMR (400MHz, CDCl3) δ7.35–7.27(m,2H),7.24–7.17(m,3H),5.71(dt,J=17.2,9.8Hz,1H),5.23–5.08(m,2H), 4.28(q, J=7.1Hz, 2H), 3.62(dt, J=8.3, 4.2Hz, 1H), 2.88–2.58(m, 2H), 2.51–2.41(m, 1H), 2.40–2.24(m, 2H), 2.01(s, 1H), 1.84–1.65(m, 2H), 1.34(t, J=7.2Hz, 3H). 13 C NMR (101MHz, CDCl3) δ164.08(t, J=33.0Hz), 141.62, 135.77, 128.35, 128.29, 125.84, 118.55, 116.57(dd, J=249.2, 248.7Hz), 72.91, 62.67, 43.59(dd , J=4.3, 2.3Hz), 36.24, 35.89 (t, J=22.7Hz), 32.05, 13.73. 19 F NMR (377MHz, CDCl3) δ-101.44 (dt, J = 261.5, 15.0Hz, 1F), -105.06 (dt, J = 260.7, 17.9Hz, 1F). HRMS-ESI (m / z) [M+Na ] + calculated for C 17 h 22 f 2 NaO 3 ,335.1435,found 335.1431.

Embodiment 2

[0035] use replace The experimental steps and purification methods were carried out according to the exploratory experiments. RF=0.4 (EA:PE=1:3), eluent: petroleum ether / ethyl acetate=20 / 1, the yield was 71%, and the product was a colorless liquid. 1 H NMR (400MHz, CDCl3) δ5.75 (dt, J = 18.3, 9.3Hz, 1H), 5.24–4.97 (m, 2H), 4.26 (q, J = 7.1Hz, 2H), 2.76 (dd, J = 9.0,4.2Hz,1H),2.53(dq,J=9.1,4.6Hz,1H),2.47–2.16(m,2H),1.87(s,1H),1.32(t,J=7.1Hz,3H), 1.01–0.83(m,1H),0.68–0.40(m,2H),0.37–0.10(m,2H). 13 C NMR (101MHz, CDCl3) δ164.13(t, J=32.7Hz), 136.55, 118.19, 116.15(dd, J=251.7, 248.9Hz), 78.85, 62.64, 44.22(dd, J=4.9, 2.5Hz) ,35.87(t,J=22.8Hz),15.17,13.81,3.12,2.73. 19 F NMR (377MHz, CDCl3) δ-101.43 (dt, J = 261.5, 15.0Hz, 1F), -105.04 (dt, J = 260.7, 17.9Hz, 1F). HRMS-ESI (m / z) [M+Na ] + calculated for C 12 h 18 f 2 NaO 3 ,271.1122,found 271.1137.

Embodiment 3

[0037] use replace The experimental steps and purification methods were carried out according to the exploratory experiments. RF=0.4 (EA:PE=1:3), eluent: petroleum ether / ethyl acetate=20 / 1, the yield was 74%, and the product was a colorless liquid. 1H NMR (400MHz, CDCl3) δ5.77–5.51(m,1H),5.22–5.12(m,3H),4.27(q,J=7.1Hz,2H),4.21(dd,J=9.0,6.5Hz, 1H), 2.38(ddt, J=12.9, 6.2, 2.9Hz, 1H), 2.34–2.22(m, 1H), 2.21–2.07(m, 1H), 1.76(d, J=1.4Hz, 3H), 1.73 (dd,J=3.3,1.4Hz,1H),1.69(d,J=1.4Hz,3H),1.34(t,J=7.2Hz,3H). 13 C NMR (101MHz, CDCl3) δ164.10 (t, J = 32.8Hz), 137.74, 136.95, 124.51, 119.11, 116.06 (dd, J = 252.0, 249.0Hz), 69.95, 62.70, 44.94 (dd, J = 4.7 ,2.7Hz), 35.33(t, J=22.9Hz), 25.93, 18.48, 13.89. 19 F NMR (377MHz, CDCl3) δ-100.34(t, J=14.8Hz), -101.04(t, J=14.6Hz), -104.02(t, J=18.0Hz), -104.71(t, J=17.8Hz ).HRMS-ESI(m / z)[M+Na] + calculated for C 13 h 20 f 2 NaO 3 ,285.1278,found285.1268.

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Abstract

The invention provides a method for preparing homoallyl alcohol compounds, a synthesis method and application thereof, and belongs to the field of organic chemistry. At room temperature and inert gas protection, in the presence of organic photosensitizers, titanium catalysts and electron donors, aldehydes or ketones react with 1,3-butadiene derivatives and halogenated alkanes under blue light irradiation to obtain homoallylic alcohols with high selectivity class of compounds. The method has the advantages of mild reaction conditions, short reaction steps, simple post-treatment, and high stereoselectivity and regioselectivity of reaction products. At the same time, this method can be used for the derivatization of natural products.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a method for preparing homoallyl alcohol compounds, a synthesis method and an application thereof. Background technique [0002] Homoallylic alcohols are important building blocks for the synthesis of various pharmaceuticals and biologically active natural substances. The incorporation of allyl metal complexes on the carbonyl group is one of the most efficient methods to obtain homoallylic alcohols, which has promoted the rapid development of synthetic chemistry and medicinal chemistry in the past few decades. However, the tedious and uneconomical preparation methods relying on preactivated allyl halides and stoichiometric metal reducing agents limit their applications. Therefore, the development of a simple, economical and environmentally friendly synthetic method for homoallylic alcohol compounds, and its application to the synthesis of biologically active natural substances, wi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/732C07C67/343C07D307/54C07D309/10C07D333/60C07C43/178C07C41/30C07C33/48C07C29/38C07J9/00C07J17/00
CPCC07B2200/07C07C29/38C07C33/483C07C41/30C07C43/1787C07C67/343C07C69/732C07D307/54C07D309/10C07D333/60C07J9/005C07J17/00C07C2601/02
Inventor 石磊厉熙宇李富盛林爽杰陈昱清史彩哲
Owner DALIAN UNIV OF TECH
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