Method for preparing chiral alpha-arylcarbonyl compound and product

An aryl carbonyl and compound technology, which is applied in the field of organic chemical synthesis, can solve the problems of complicated steps and difficult to obtain raw materials, and achieves the effect of cheap and easy-to-obtain raw materials

Active Publication Date: 2021-07-20
ZHEJIANG NORMAL UNIVERSITY
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  • Abstract
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Problems solved by technology

However, this type of method uses a strong base, the steps

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  • Method for preparing chiral alpha-arylcarbonyl compound and product
  • Method for preparing chiral alpha-arylcarbonyl compound and product
  • Method for preparing chiral alpha-arylcarbonyl compound and product

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[0047] The specific implementation examples of the new method for preparing chiral α-arylcarbonyl compounds provided by the present invention are introduced below, and multiple specific implementation examples are provided. It should be noted that the implementation of the present invention is not limited to the following implementation examples.

[0048] In the embodiment, the raw material (II) adopts commercially available products, and the raw material (III) is partially derived from commercially available products, and the preparation method of some compounds is as follows:

[0049] (S)-4-isobutyl-2-pentyl-4,5-dihydrooxazole (6a):

[0050] 0 ℃ to (S)-2-amino-3-methylbutyl-1-yl alcohol (2.48g, 24mmol) and Et 3 To a solution of N (3.3 mL, 24 mmol) in DCM (67 mL), hexanoyl chloride (2.8 mL, 20 mmol) was added dropwise. The mixture was warmed to room temperature, stirred for 3 h, DCM (33 mL) and Et 3 N (13.9 mL, 100 mmol). MsCl (1.9 mL, 24 mmol) was added at 0° C. and stir...

Embodiment 1

[0062] R 1 for H, R 2 is n-butyl, R 3 For isopropyl group, 238.9 mg of yellow liquid compound 1 was obtained by the above method, and the yield was 62% (>20 / 1dr). 1 H NMR (600MHz, CDCl 3 ):δ7.85–7.81(m,1H),7.44–7.40(m,1H),7.33–7.27(m,1H),6.95–6.89(m,1H),4.21–4.16(m,1H),4.02 (t,J=7.6Hz,1H),3.98–3.93(m,1H),3.89(t,J=7.9Hz,1H),2.07–1.96(m,1H),1.85–1.79(m,2H), 1.37–1.30(m,3H),1.24–1.18(m,1H),0.93(d,J=6.8Hz,3H),0.88–0.83(m,6H).

[0063] 13 C NMR (151MHz, CDCl 3 ): δ167.9, 143.5, 139.7, 128.7, 128.6, 128.0, 102.0, 71.9, 69.5, 49.0, 34.2, 32.4, 29.6, 22.7, 19.1, 17.8, 14.1.

[0064] IR(neat):2955,2928,2870,1661,1465,1435,1106,745.

[0065] HRMS (ESI-TOF): calculated for [C 17 h 25 INO(M+H + )]:386.0975,found:386.0976.

Embodiment 2

[0067] R 1 for H, R 2 is isopentyl, R 3 For isopropyl group, 231.6 mg of yellow liquid compound 2 (>20 / 1dr) can be obtained by the same method, and the yield is 58%. 1 H NMR (400MHz, CDCl 3 ):δ7.85–7.80(m,1H),7.44–7.40(m,1H),7.32–7.27(m,1H),6.94–6.88(m,1H),4.21–4.16(m,1H),4.00 (t,J=7.6Hz,1H),3.98–3.93(m,1H),3.90(t,J=7.9Hz,1H),2.04–1.96(m,1H),1.87–1.78(m,2H), 1.60–1.51(m,1H),1.30–1.22(m,1H),1.15–1.05(m,1H),0.93(d,J=6.8Hz,3H),0.88–0.82(m,9H).

[0068] 13 C NMR (101MHz, CDCl 3 ): δ168.0, 143.4, 139.7, 128.7, 128.6, 128.0, 102.0, 71.7, 69.5, 49.2, 36.4, 32.27, 32.25, 28.0, 22.7, 22.6, 19.1, 17.7.

[0069] IR(neat):2953,2899,2869,1662,1465,1384,1365,1170,1010,742.

[0070] HRMS (ESI-TOF): calculated for [C 18 h 27 INO((M+H + )]:400.1132,found:400.1129.

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Abstract

The invention discloses a method for preparing a chiral alpha-aryl carbonyl compound, which comprises the following steps: activating an R2 substituted iodobenzene diacetate compound by Lewis acid, and then reacting with an R3 stereosubstituted oxazoline compound in the presence of alkali to obtain the chiral alpha-aryl carbonyl compound, wherein R1 is selected from H, one or more alkyl groups, one or more halogenated alkyl groups, alkoxycarbonyl, halogen or multi-substitution formed by the combination of the above atoms, R2 is selected from H, alkyl and substituted alkyl, wherein a substituent group is selected from cycloalkyl, halogen, alkoxy, heterocycloalkyl, substituted heterocycloalkyl, aryl, cyano, aryloxy and carbonyl, and R3 is selected from alkyl, substituted alkyl and aryl. The method has the advantages of mild reaction conditions, good stereoselectivity, easy product separation and simple operation.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, in particular to a new method and product for preparing chiral α-aryl carbonyl compounds. Background technique [0002] Due to the importance of α-aryl compounds, they have been extensively studied, and chiral α-arylcarbonyl compounds are one of them. At present, it is an important intermediate in the synthesis of many active pharmaceutical molecules. Chiral α-arylcarbonyl compounds are mainly used in the field of medicine; [0003] Chiral α-arylcarbonyl compounds have important pharmaceutical and physiological activities in the field of medicine. (J. Med. Chem., 1970, 13:203; Curr. Drug Metab. 2001, 2:37.). [0004] So far, some synthetic methods of chiral α-arylcarbonyl compounds have been reported successively. [0005] The transition metal palladium catalytic coupling system under the action of chiral ligands has been reported to be used to prepare chiral α-aryl carbonyl compound...

Claims

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Application Information

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IPC IPC(8): C07D263/10C07D263/14C07D413/06
CPCC07D263/10C07D263/14C07D413/06C07B2200/07
Inventor 李开笑张其峰李东阳罗凡田俊松彭勃
Owner ZHEJIANG NORMAL UNIVERSITY
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