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Homoallylamine compound as well as synthesis method and application thereof

A synthesis method and high allylamine technology are applied in the directions of steroid, cyanide reaction preparation, chemical instruments and methods, etc., can solve the problems of cumbersome methods, uneconomical, waste of resources and the like, and achieve high reaction yield and selectivity. high effect

Inactive Publication Date: 2022-06-24
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation methods relying on preactivated allyl halides and stoichiometric metal reducing agents are tedious and uneconomical, and cause environmental pollution and waste of resources.

Method used

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  • Homoallylamine compound as well as synthesis method and application thereof
  • Homoallylamine compound as well as synthesis method and application thereof
  • Homoallylamine compound as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038]

[0039] 4a, the experimental steps and purification methods were carried out with reference to the exploratory experiment. RF=0.5 (EA:PE=1:5), eluent: petroleum ether / ethyl acetate=10 / 1, the yield is 87%, and the product is a colorless liquid.

[0040] 1 H NMR (400MHz, CDCl 3 ): δ7.18–7.07 (m, 2H), 6.81 (d, J=8.7Hz, 2H), 6.74 (s, 2H), 5.55–5.43 (m, 1H), 5.44–5.26 (m, 1H), 4.10(dd, J=7.7, 5.9Hz, 1H), 3.78(s, 3H), 3.24(s, 1H), 2.72-2.45(m, 2H), 2.27-2.17(m, 7H), 2.12(s, 6H), 1.43(s, 9H). 13 C NMR (101MHz, CDCl 3 ):δ172.43,158.45,142.08,135.80,131.37,130.52, 129.44,129.06,127.84,127.47,113.57,80.07,61.15,55.13,39.95,35.26,28.06,(28.8.03)RMS-ESI. [M+H] + calculated for C 27 H 38 NO 3 ,424.2852, found:424.2841.

Embodiment 2

[0042] use replace The experimental steps and purification methods were carried out with reference to the exploratory experiments. RF=0.5 (EA:PE=1:5), eluent: petroleum ether / ethyl acetate=20:1, the yield is 65%, and the product is a colorless liquid.

[0043] 1 H NMR (400MHz, CDCl 3 ):δ7.24(dd,J=26.8,8.4Hz,2H),7.13(d,J=8.4Hz,2H),6.74(dd,J=128.5,48.0Hz,2H),5.61–5.44(m, 1H), 5.34(d, J=7.1Hz, 1H), 4.14(dt, J=399.6, 7.5, 5.9Hz, 1H), 3.25(s, 1H), 2.57(ddd, J=37.4, 14.0, 7.1Hz , 2H), 2.21(d, J=8.7Hz, 7H), 2.10(s, 6H), 1.43(s, 9H). 13 C NMR (101MHz, CDCl 3 ):δ172.34,142.22,132.48,132.05,130.76,130.40,129.56,128.91,128.33,128.22,126.75,80.13,61.13,40.02,35.17,28.06,27.99,20.45,19 +H] + calculated for C 26 H 35 ClNO 2 ,428.2356,found:428.2344.

Embodiment 3

[0045] use replace The experimental steps and purification methods were carried out with reference to exploratory experiments. RF=0.5 (EA:PE=1:5), eluent: petroleum ether / ethyl acetate=20 / 1, the yield is 78%, and the product is a colorless liquid.

[0046] 1 H NMR (400MHz, CDCl 3 ): δ7.39(d,J=8.4Hz,2H),7.08(dd,J=8.6,2.1Hz,2H),6.74(s,2H),5.58–5.46(m,1H),5.39–5.28( m,1H),4.19–4.09(m,1H),3.25(s,1H),2.55(dq,J=36.8,7.1Hz,2H),2.20(d,J=9.1Hz,7H),2.10(d , J=4.4Hz, 6H), 1.42(s, 9H). 13 CNMR (101MHz, CDCl 3 ): δ172.33, 142.78, 141.89, 132.06, 131.25, 130.67, 129.54, 128.82, 128.55, 126.70, 120.56, 80.12, 61.10, 40.02, 35.14, 28.04, 27.97, 20.43, RMS +H] + calculated for C 26 H 35 BrNO 2 , 474.1831,found:474.1814.

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Abstract

The invention provides a homoallylamine compound as well as a synthesis method and application thereof, and belongs to the field of organic chemistry. In the presence of an organic photosensitizer and an electron donor, imine reacts with a 1, 3-butadiene derivative and halogenated alkane under the irradiation of blue light at room temperature under the protection of inert gas, and the high-allylamine compound is obtained with high selectivity. The method has the advantages of mild reaction conditions, short reaction steps, simple post-treatment and high stereoselectivity and regioselectivity of reaction products. Meanwhile, the method can be used for derivatization of natural products and post-modification of drug molecules.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a high allylamine compound, a synthesis method and applications thereof. Background technique [0002] Homoallylamine compounds are an important part of the synthesis of various drugs and natural substances with biological activity. The addition of allyl metal complexes on the carbon-nitrogen double bonds of imines is one of the most efficient methods to obtain homoallylamines, which has promoted the rapid development of synthetic chemistry and medicinal chemistry in the past few decades. However, the method that relies on the preparation of pre-activated allyl halohydrocarbon and stoichiometric amount of metal reducing agent is cumbersome and uneconomical, and causes environmental pollution and waste of resources. Therefore, the development of simple, economical, and environmentally friendly synthetic methods for homoallylamine compounds, and their application to the synthesis of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/34C07C227/00C07D305/06C07D333/24C07J9/00C07J1/00C07D209/26C07C311/21
CPCC07C229/34C07D305/06C07D333/24C07J1/0014C07D209/26C07J9/005C07C311/21
Inventor 石磊宋冰坤陈昱清林爽杰史彩哲张丹丹
Owner DALIAN UNIV OF TECH
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