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Method for carrying out trans-Micheal addition reaction by taking compound with aurone skeleton as receptor

An addition reaction and compound technology, applied in the field of trans-Micheal addition reaction, to achieve the effects of high efficiency and convenience, wide substrate applicability and high atom economy.

Active Publication Date: 2020-06-05
QINGDAO AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the α-functionalization of heterodienes via the Michael pathway remains a challenge

Method used

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  • Method for carrying out trans-Micheal addition reaction by taking compound with aurone skeleton as receptor
  • Method for carrying out trans-Micheal addition reaction by taking compound with aurone skeleton as receptor
  • Method for carrying out trans-Micheal addition reaction by taking compound with aurone skeleton as receptor

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041]

[0042] Orange ketone compound 1a (0.1mmol) was subjected to trans-Michael addition in solvent (1.0mL) under the action of catalyst (20mol%, 0.02mmol) to obtain addition product 2a, and the conditions such as its catalyst, solvent and temperature were as follows: Table 1 shows:

[0043] Table 1

[0044] serial number catalyst solvent temperature(℃) time (h) Yield(%) 1 Cu(OTf) 2

DCE 120 1.5 23 2 Zn(OTf) 2

DCE 120 1.5 42 3 Mg(OTf) 2

DCE 120 1.5 n.r. 4 Sc(OTf) 3

DCE 120 1.5 94 5 TsOH·H 2 o

DCE 120 1.5 39 6 (-)-CSA DCE 120 1.5 72 7 TfOH DCE 120 1.5 57 8 Sc(OTf) 3

EtOH 120 1.5 84 9 Sc(OTf) 3

DCM 120 1.5 94 10 Sc(OTf) 3

toluene 120 1.5 75 11 Sc(OTf) 3

THF 120 1.5 43 12 Sc(OTf) 3

CH 3 CN

120 1.5 60 13 Sc(OTf) 3

DCM 80 3.5 89 14 Sc(OTf) 3

DCM 60 5.0 81 ...

Embodiment 2

[0054] Product chemical formula: C 20 h 20 NO 2

[0055] Molecular weight: 306.15

[0056] Structural formula:

[0057]

[0058] Yield: 43%

[0059] 1 H NMR (500MHz, CDCl 3 )δ7.70(dd, J=7.9,1.5Hz,1H),7.61–7.58(m,1H),7.13–7.07(m,2H),6.94(d,J=7.5Hz,1H),6.49(dd ,J=7.5,1.6Hz,1H),6.42(d,J=1.7Hz,1H),3.83(dd,J=10.0,5.6Hz,1H),3.55(td,J=8.7,2.1Hz,1H) ,3.35–3.23(m,2H),2.79(d,J=16.3Hz,1H),2.33(s,3H),2.05–1.97(m,1H),1.97–1.89(m,1H),1.77–1.69 (m,1H),1.42–1.32(m,1H);

[0060] 13 C NMR (126MHz, CDCl 3 )δ202.30, 172.09, 143.16, 138.08, 137.73, 129.04, 124.21, 121.97, 121.30, 116.92, 114.56, 113.65, 111.65, 84.32, 61.49, 47.58, 35.72, 25.54, 21.

Embodiment 3

[0062] Product chemical formula: C 20 h 20 NO 3

[0063] Molecular weight: 322.14

[0064] Structural formula:

[0065]

[0066] Yield: 71%

[0067] 1 H NMR (500MHz, CDCl 3 )δ7.70(d, J=7.8Hz, 1H), 7.59(t, J=7.8Hz, 1H), 7.09(dt, J=7.4, 3.1Hz, 2H), 6.95(d, J=8.2Hz, 1H), 6.24(dd, J=8.2, 2.4Hz, 1H), 6.16(d, J=2.5Hz, 1H), 3.80(s, 4H), 3.52(t, J=8.7Hz, 1H), 3.27( dt,J=16.6,5.1Hz,2H),2.77(d,J=16.2Hz,1H),2.06–1.97(m,1H),1.97–1.87(m,1H),1.76–1.66(m,1H) ,1.42–1.31(m,1H); 13 CNMR (126MHz, CDCl 3 )δ202.16,172.07,159.85,144.25,138.10,129.70,124.22,122.01,121.27,113.64,110.28,100.88,97.34,84.38,61.44,55.20,47.56,35.42,235.5

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Abstract

The invention provides a method for carrying out a trans-Micheal addition reaction by taking a compound with an aurone skeleton as a receptor, and belongs to the technical field of chemical synthesis.According to the method, a reaction can be carried out under the conditions that Sc(OTf) 3 is used as a catalyst, the temperature is 80 DEG C and dichloromethane is used as a solvent. According to the method provided by the invention, the alpha-functionalized trans-Michael addition product of oxadiene is obtained through a negative hydrogen migration / aromatization / dearomatization / cyclization reaction by taking a carbonyl group conjugated with an aurone skeleton compound and a double bond as a receptor for Michael addition under the catalysis of Lewis acid. The method is simple and practical to operate, efficient and convenient in reaction, wide in substrate applicability and extremely high in atom economy.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a compound with an aurone skeleton as an acceptor for trans-Micheal addition reaction. Background technique [0002] The helical loop structure widely exists in biologically active natural products and drugs, and is usually an ideal structure for new drug development due to its inherent three-dimensionality and structural novelty. Among the various spirocyclic structures, the [6,5]-piperidine spirofuran structure shown in the following structure is a very important class, present in nicotinic acetylcholine receptor (nAChR) modulators, CCR1 antagonists, acetyl Coenzyme a carboxylase (ACC) inhibitors. Therefore, the synthesis of related spirocyclic backbones has attracted considerable interest in recent years. [0003] [0004] Orange ketone is a secondary metabolite in plants. It belongs to flavonoids and can be regarded as a substituted benzofuranone d...

Claims

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Application Information

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IPC IPC(8): C07D491/20C07D498/20C07D495/10C07D495/20C07D491/107C07D513/20
CPCC07B2200/07C07D491/107C07D491/20C07D495/10C07D495/20C07D498/20C07D513/20
Inventor 董凤英肖建段康
Owner QINGDAO AGRI UNIV
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