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Synthetic method of Betti base derivative

A synthesis method and a technology of derivatives, which are applied in the field of synthesis of Bety base derivatives, can solve problems such as cumbersome post-processing operations, and achieve the effects of avoiding expensive catalysts, high reaction yields, and simple operations

Inactive Publication Date: 2019-04-05
NEW MATERIAL INST OF SHANDONG ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction research of o-methylene quinone has a long history, and the Michael addition reaction based on P, S and N heteroatoms is relatively mature, but most of the reaction methods still require the use of acid-base catalysts
Such a reaction method is not suitable for the preparation of compounds containing acid-base-sensitive functional groups, and the system needs to be neutralized to neutral after the reaction, and the post-treatment operation is cumbersome

Method used

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  • Synthetic method of Betti base derivative
  • Synthetic method of Betti base derivative
  • Synthetic method of Betti base derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035]

[0036] Add 2.00 g (10 mmol) of compound I-1, 2.06 g (20 mmol) of compound II-1, and 0.49 g (1 mmol) of solid Sc(OTf) into a 100 mL round bottom flask 3, and finally 20 mL of dry 1,2-dichloroethane was added, and the resulting mixture was stirred at 80° C. for 10 hours. After the reaction mixture was cooled to room temperature, it was poured into ice water, extracted with 50mL×3 methylene chloride, and the extracted organic phases were combined, washed once with saturated brine, anhydrous Na 2 SO 4 Dry, concentrate and remove the solvent to obtain the crude product, which is separated by column chromatography to obtain the pure product of compound III-1. Oily liquid, 2.62g, yield 92%. 1 H NMR (400 MHz, CDCl 3 ) δ : 11.72 (s, 1H), 7.36 (d, J = 7.1 Hz, 2H), 7.33~7.22 (m, 3H), 7.12~7.08 (m, 1H), 6.86(dd, J = 10.9 Hz, 4.2 Hz, 2H), 6.68 (td, J = 7.5 Hz, 0.9 Hz, 1H), 4.56 (s, 1H), 2.82~2.73 (m, 2H), 2.70~2.64 (m, 6H); 13 C NMR (CDCl 3 , 100MHz) δ : 156.69, 13...

Embodiment 2

[0038]

[0039] Add 2.00g (10mmol) compound I-1, 1.76g (20mmol) compound II-1, 0.98g (2mmol) solid Sc(OTf) into a 100mL round bottom flask 3 , and finally 50 mL of dry DMF was added, and the resulting mixture was stirred at 70° C. for 6 hours until the reaction was complete. The reaction mixture was cooled to room temperature, poured into water, stirred, extracted with 50mL×3 dichloromethane, combined and extracted organic phases, washed once with saturated brine, anhydrous Na 2 SO 4 Dry, concentrate and remove the solvent to obtain the crude product, which is separated by column chromatography to obtain the pure product of compound III-2. Oily liquid, 2.32g, yield 88%. 1 H NMR (400 MHz, CDCl 3 ) δ : 11.71 (s, 1H), 7.41 (d, J = 7.1 Hz, 2H), 7.30~7.21 (m, 3H), 7.13~7.09 (m, 1H), 6.94~6.92 (m, 1H), 6.86 (d, J = 8.1 Hz, 1H), 6.71 (td, J = 7.5 Hz, 0.9 Hz, 1H), 4.39 (s, 1H), 3.77~3.72 (m, 4H), 2.58~2.42 (m, 4H); 13 C NMR (CDCl 3 , 100MHz) δ : 156.15, 139.33, 129.43,...

Embodiment 3

[0041]

[0042] Add 2.00g (10mmol) compound I-1, 1.61g (15mmol) compound II-3, 0.12g (0.5mmol) solid Sc(NO 3 ) 3 , and finally 50 mL of dry DMSO was added, and the resulting mixture was stirred vigorously at 50 °C for 5 h. After the reaction mixture was cooled to room temperature, it was poured into water, stirred, extracted with 50mL×3 dichloromethane, combined and extracted organic phases were washed once with saturated brine, anhydrous Na 2 SO 4 Dry, concentrate and evaporate the solvent to obtain the crude product, and purify by column chromatography to obtain the pure product of compound III-3. Oily liquid, 2.37g, yield 90%. 1 H NMR (400 MHz, DMSO- d 6 )δ: 11.19 (s, 1H), 7.42 (d, J = 7.4 Hz, 2H), 7.35~7.30 (m, 6H), 7.27~7.21 (m, 2H), 7.08~7.04 (m, 2H), 6.73 (dd, J = 13.5Hz, 7.4Hz, 2H), 5.01(s, 1H), 3.66(s, 2H); 13 C NMR (DMSO- d 6 , 100 MHz) δ:156.85, 143.24, 140.07, 128.78, 128.71, 128.69, 128.34, 128.23, 127.97, 127.92, 127.41, 127.34, 119.29, 116.25, 62....

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Abstract

The invention provides a synthetic method of a Betti base derivative. The Betti base derivative is prepared by: subjecting to 2-(hydroxy(phenyl)methyl)phenol compound and an amine compound to Sc(III)catalysis to generate an o-quinone methide, and carrying out nucleophilic addition; the product yield is 78-95%. The synthetic method is simple to perform; the materials and the reagents are simple; the reaction yield is high; the defects are avoided that a catalyst for the prior art is expensive and conditions for the prior art are strict; the product is easy to isolate and purify; the syntheticmethod is important to the synthesis of Betti base derivatives and has important value in the methodological study on o-quinone methides.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for synthesizing Bety base derivatives. Background technique [0002] Betti base was first synthesized by Italian chemist Betti in the early 20th century. Betti bases and their derivatives are the key components of natural products and drug molecules with biological activity, such as antibacterial agents, fungicides, anti-tumor agents, and anti-tuberculosis agents. In addition, Betti base and its derivatives have a very suitable 1,3-aminophenol ligand structure, which can form a stable six-membered ring coordination structure with many metal ions. As a chiral ligand, the only chiral carbon atoms of the Betti base are respectively connected to the naphthalene ring and the benzene ring, so that the substrate has better stereoselectivity when it is close to the ligand center. Therefore, Betti bases and their derivatives show excellent catalytic activity in catal...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/02C07C215/50
CPCC07C213/02C07C215/50
Inventor 张硕彭丹王峰侯梓桐刘一帆宋子贺
Owner NEW MATERIAL INST OF SHANDONG ACADEMY OF SCI
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