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Chiral aryl allyl amine compound and synthesis method thereof

A technology of aryl allyl amine and amine compounds, which is applied in the field of chiral aryl allyl amine compounds and their synthesis, can solve the problems of complex chiral ligand structures, residual metal products, and expensive catalysts, etc. Achieve the effect of low cost, high optical purity and easy operation

Inactive Publication Date: 2018-11-23
CHANGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] All of the above use the method of transition metal catalysis, the catalyst is relatively expensive, and may cause the problem of metal residue in the product. In addition, the required chiral ligand has a complex structure and requires multi-step synthesis to obtain

Method used

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  • Chiral aryl allyl amine compound and synthesis method thereof
  • Chiral aryl allyl amine compound and synthesis method thereof
  • Chiral aryl allyl amine compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] At room temperature, dissolve 9.3mg of aniline and 14.6mg of MBH adduct with tert-butoxyloxyl group in 0.5mL of p-xylene, add 17.1mg of hydroquinidine (anthraquinone-1,4-diyl) Diether ((DHQD) 2AQN) and 19.5mg of calcium fluoride were stirred at room temperature for 72 hours, the solvent was removed, and the residue was separated by column chromatography to obtain the desired compound, whose molecular structural formula was: It is a colorless oil, 80% yield, 92% ee, [determined by high performance liquid chromatography, chiral OD-H column, n-hexane:isopropanol=95:5, 0.5mL / min, 254nm, t R (major)=8.57min,t R (minor)=10.76min]. Optical rotation value (c=0.7, CHCl 3 ), 1 H NMR (300MHz, CDCl 3 ):δ=7.28-7.40(m,5H),7.14-7.20(m,2H),6.70-6.74(m,1H),6.58(dd,J=8.6Hz,J=0.9Hz,2H),6.40( s,1H),5.97(t,J=1.2Hz,1H),5.41(s,1H),4.16(s,1H),3.70(s,3H); 13 C NMR (100MHz, CDCl 3 ):166.8,146.8,140.7,140.0,129.3,128.9,128.0,127.7,126.3,118.0,113.5,59.0,52.0.HRMS(ESI):C 17 h 18 NO 2 ...

Embodiment 2

[0036] At room temperature, 19.7 mg of 1,8-naphthalimide and 14.6 mg of MBH adducts with tert-butoxyacyloxy were dissolved in 0.5 mL of p-xylene, and 17.1 mg of hydrogenated quinidine (anthracene Quinone-1,4-diyl)diether ((DHQD)2AQN) and 19.5mg of calcium fluoride were stirred at room temperature for 72 hours, the solvent was removed, and the residue was separated by column chromatography to obtain the desired compound, which The molecular structural formula is: It is a colorless oil, 71% yield, 92% ee, [determined by high performance liquid chromatography, chiral AD-H column, n-hexane:isopropanol=90:10, 1mL / min, 254nm, t R(major)=24.84min,t R (minor) = 29.00 min]. Optical rotation value (c=0.3, CH 2 Cl 2 ), 1 H NMR (300MHz, CDCl 3 ): δ=8.56(d, J=7.2Hz, 2H), 8.16(d, J=8.2Hz, 2H), 7.70(t, J=7.8Hz, 2H), 7.57(d, J=7.4Hz, 2H ),7.26-7.36(m,3H),7.20(s,1H),6.47(d,J=1.4Hz,1H),5.60(d,J=1.7Hz,1H),3.67(s,3H); 13 C NMR (100MHz, CDCl 3 ):166.7,164.4,139.2,137.8,134.0,131.6,131....

Embodiment 3

[0038] At room temperature, 12.5 mg of methyl 2-pyrrolecarboxylate and 14.6 mg of MBH adduct with tert-butoxyloxyl group were dissolved in 0.5 mL of p-xylene, and 17.1 mg of hydroquinidine (anthraquinone-1, 4-diyl) diether ((DHQD) 2AQN) and 19.5mg of calcium fluoride were stirred at 50°C for 72 hours, the solvent was removed, and the residue was separated by column chromatography to obtain the desired compound, whose molecular structure was : It is a colorless oil, 50% yield, 84% ee, [determined by high performance liquid chromatography, chiral AD-H column, n-hexane:isopropanol=90:10, 1mL / min, 254nm, t R (major)=7.99min,t R (minor)=9.92min]. Optical rotation value (c=0.44, CH 2 Cl 2 ), 1 H NMR (300MHz, CDCl 3 ):δ=7.49(s,1H),7.31-7.37(m,3H),7.21(d,J=7.4Hz,2H),7.04(t,J=1.9Hz,1H),6.63(s,1H) ,6.44(s,1H),6.11(t,J=3.1Hz,1H),5.01(s,1H),3.78(s,3H),3.70(s,3H); 13 C NMR (100MHz, CDCl 3 ):165.9,161.4,141.4,137.78,128.9,128.6,128.4,127.5,127.3,122.2,119.1,108.3,61.2,52.4,51.3....

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Abstract

The invention discloses a chiral aryl allyl amine compound and a synthesis method thereof, and belongs to the technical field of chemical pharmacy and fine chemical engineering. The compound is a kindof important synthetic intermediate. The compound per se has wide bioactivity. The cheap and easy-to-obtain aryl amine compound takes nucleophilic SN2' substitution reaction with MBH reaction adductswith leaving groups under the effects of chiral tertiary amine catalysts; a serious of high-degree optical pure aryl allyl amine compounds are synthesized at high yield. The invention provides a simple fast and practical technical route for the preparation of the chiral aryl allyl amine compound. Wide application is realized in the technical fields of chemical pharmacy and fine chemical engineering.

Description

technical field [0001] The present invention relates to the synthesis of chiral amine compounds, that is, the efficient synthesis of chiral aryl allyl amine compounds, mainly related to the asymmetric nucleophilicity of nucleophiles to MBH adducts with leaving groups under organic catalysis SN2' substitution reaction, the present invention provides an efficient, concise and practical route for the synthesis of chiral aryl allyl amine compounds, which has broad application prospects in the fields of chemical pharmacy and fine chemical industry, and belongs to chemical pharmacy and fine chemical industry Preparation technology field. Background technique [0002] Chiral aryl allylamine compounds are highly functionalized molecules, which are an important class of intermediates in organic synthesis. Many natural products and bioactive molecules can be synthesized through subsequent transformations. For example, α-methylene β-lactam compounds with anti-tumor activity can be syn...

Claims

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Application Information

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IPC IPC(8): C07C229/34C07D221/14C07D207/34C07C227/32
CPCC07B2200/07C07C227/32C07C229/34C07D207/34C07D221/14
Inventor 赵帅陈新陈至立金雷
Owner CHANGZHOU UNIV
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