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A method and product for preparing chiral α-aryl carbonyl compound

A technology of aryl carbonyl and compound, applied in the field of organic chemical synthesis, can solve the problems of cumbersome steps and difficult to obtain raw materials, and achieve the effect of cheap and easy-to-obtain raw materials

Active Publication Date: 2022-04-19
ZHEJIANG NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this type of method uses a strong base, the steps are cumbersome, and the raw materials are not easy to obtain

Method used

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  • A method and product for preparing chiral α-aryl carbonyl compound
  • A method and product for preparing chiral α-aryl carbonyl compound
  • A method and product for preparing chiral α-aryl carbonyl compound

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preparation example Construction

[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 α-aryl carbonyl compound, comprising: R 2 The substituted iodobenzene diacetate compound was activated with Lewis acid and then reacted with R 3 Stereo-substituted oxazoline compounds react in the presence of a base to obtain the chiral α-aryl carbonyl compound; the R 1 R 2 selected from H, alkyl, substituted alkyl, wherein the substituent is selected from cycloalkyl, halogen, alkoxy, heterocycloalkyl, substituted heterocycloalkyl, aryl, cyano, aryloxy, carbonyl; R 3 Selected from alkyl, substituted alkyl, aryl. The method has mild reaction conditions, good stereoselectivity, easy separation of products 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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Patent Type & Authority Patents(China)
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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