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Penta-substituted 3-alkenylene cyclopentene derivative as well as synthesis method and application thereof

A technology for the synthesis of alkenylene cyclopentene, which is applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, chemical/physical processes, etc., and can solve the problem of directly constructing 3-alkenylene Cyclopentene compounds, raw materials are not easy to obtain, and the environment is not friendly, etc., to achieve the effect of easy synthesis and modification, excellent yield, and environmental friendliness

Inactive Publication Date: 2021-11-02
LINYI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the synthesis method reported above, the main problems are: 1) most of the reaction substrates are allenes / alkynes, the raw materials are not easy to obtain, multi-step synthesis is required and the stability is poor; The processing is relatively complicated and unfriendly to the environment; 3) the reaction time of some reactions is too long and needs to be as long as 36 hours; 4) the yield and universality of the reaction need to be further improved; the above-mentioned synthetic method has advantages in terms of cost and environmental protection certain limitations
In addition, these methods are difficult to directly construct 3-alkenylene cyclopentene compounds, especially it is difficult to introduce a carbamoylmethyl group at the 5-position that can be further derivatized

Method used

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  • Penta-substituted 3-alkenylene cyclopentene derivative as well as synthesis method and application thereof
  • Penta-substituted 3-alkenylene cyclopentene derivative as well as synthesis method and application thereof
  • Penta-substituted 3-alkenylene cyclopentene derivative as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis of 1-phenyl-5-methyl-5-(N-methyl-N-Tscarbamoylmethyl)-3-(2-propenylidene)cyclopentene (IA)

[0030]

[0031] Under nitrogen atmosphere, add 0.3mmol of 3-methyl-3-butene-1-ynamine compound, 0.36mmol of acetylenic alcohol, 3mL of 1,2-dichloroethane, PPh into a 10ml reaction tube 3 AuCl 0.03mmol, AgOTf 0.03mmol. React at 25°C for 6 hours to obtain the target product formula (IA), a light yellow oily liquid, with an isolation yield of 80%.

[0032] Product NMR data: 1H NMR (400MHz, CDCl 3 ):δ7.55(d,J=8.2Hz,2H),7.20-7.27(m,7H),6.39(s,1H),3.21(s,3H),3.07(d,J=17.1Hz,1H) ,2.74(d,J=17.0Hz,1H),2.72(d,J=15.7Hz,1H),2.48(d,J=16.2Hz,1H),2.40(s,3H),1.77(s,3H) ,1.67(s,3H),1.31(s,3H);13C NMR(100MHz,CDCl3):δ171.5,152.6,144.5,137.3,136.5,136.4,129.8,128.6,128.1,127.5,127.1,126.9,122.8,48.4 , 44.9, 44.3, 32.9, 26.9, 21.5, 21.2, 20.6.

[0033] High resolution mass spectrometry data: HRMS(ESI,m / z)calcd.for C 25 h 29 NNaO 3 S[M+Na]+calc.: 446.1766; found: 446.1759.

Embodiment 2

[0035] Synthesis of 1-(4-bromophenyl)-5-methyl-5-(N-methyl-N-Tscarbamoylmethyl)-3-(2-propenylidene)cyclopentene (IB)

[0036]

[0037] Under nitrogen atmosphere, add 0.3mmol of 3-methyl-3-butene-1-yneamine compound, 0.36mmol of acetylenic alcohol, 3mL of 1,2-dichloroethane, PPh into a 10ml reaction tube 3AuCl 0.03mmol, AgOTf 0.03mmol. React at 25°C for 5 hours to obtain the target product formula (IB), a pale yellow oily liquid with an isolated yield of 70%.

[0038] Product NMR data: 1H NMR (400MHz, CDCl 3 ): δ7.48(d, J=8.2Hz, 2H), 7.30(d, J=8.4Hz, 2H), 7.18(d, J=8.2Hz, 2H), 7.05(d, J=8.4Hz, 2H ),3.15(s,3H),2.95(d,J=17.2Hz,1H),2.68(d,J=17.2,2H),2.37-2.41(m,4H),1.71(s,3H),1.60( s,3H),1.22(s,3H);13C NMR(100MHz,CDCl3):δ171.3,151.0,144.7,136.4,136.2,136.2,131.2,129.9,129.2,129.1,127.0,123.7,120.8,48.3,44.8, 44.3, 32.9, 27.2, 21.6, 21.3, 20.7.

[0039] High resolution mass spectrometry data: HRMS(ESI,m / z)calcd.for C 25 h 28 BrNNaO 3 S[M+Na]+calc.: 524.0871; found: 524.0...

Embodiment 3

[0041] Synthesis of 1-(4-nitrophenyl)-5-methyl-5-(N-methyl-N-Tscarbamoylmethyl)-3-(2-propenylidene)cyclopentene (IC)

[0042]

[0043] Under nitrogen atmosphere, add 0.3mmol of 3-methyl-3-butene-1-ynamine compound, 0.36mmol of acetylenic alcohol, 3mL of 1,2-dichloroethane, PPh into a 10ml reaction tube 3 AuCl 0.03mmol, AgOTf 0.03mmol. React at 25°C for 4 hours to obtain the target product formula (IC), a pale yellow oily liquid with an isolated yield of 75%.

[0044] Product NMR data: 1H NMR (400MHz, CDCl 3 ): δ8.00(d, J=8.9Hz, 2H), 7.55(d, J=8.4Hz, 2H), 7.37(d, J=9.0Hz, 2H), 7.21(d, J=8.1Hz, 2H ),6.59(s,1H),3.10-3.14(m,4H),2.78(d,J=17.2Hz,1H),2.72(d,J=16.0Hz,1H),2.36-2.43(m,4H) ,1.77(s,3H),1.64(s,3H),1.32(s,3H); 13C NMR(100MHz,CDCl3):δ170.9,149.5,146.1,144.9,143.9,136.2,136.0,131.7,129.8,127.4, 126.9, 126.5, 123.3, 48.2, 44.6, 44.5, 32.8, 27.5, 21.4, 21.4, 20.7.

[0045] High resolution mass spectrometry data: HRMS(ESI,m / z)calcd.for C 25 h 29 N 2 o 5 S[M+H]+calc.:...

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Abstract

The invention discloses a penta-substituted 3-alkenylene cyclopentene derivative and a synthesis method thereof. The synthesis method comprises the specific steps that 3-methyl-3-butene-1-alkyne amine compounds and alkynol compounds are used as raw materials, an organic solvent and a catalyst are added in the atmosphere of protective gas, and catalytic synthesis is carried out to obtain the penta-substituted 3-alkenylene cyclopentene derivative as shown in the formula (I). The preparation method has the advantages of simple and easily available raw materials, mild reaction conditions, good substrate universality, high atom economy, high reaction yield, simple post-treatment, environmental friendliness and the like. The invention also discloses an application of the penta-substituted 3-alkenylene cyclopentene derivative as shown in the formula (I) in synthesis and modification of related natural products and drug molecules.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, in particular to a pentasubstituted 3-alkenylene cyclopentene derivative and its synthesis method and application Background technique [0002] 3-alkenylidene cyclopentene derivatives are an important class of organic compounds, which are the core skeleton of many natural products and drug molecules, and have a wide range of physiological and pharmacological effects. In addition, 3-alkenylidene cyclopentene derivatives can be used as organic synthesis intermediates because of their conjugated double bonds in their molecules, which is convenient for further derivatization, and is convenient for the synthesis and modification of related drug molecules, natural products and functional materials, etc. has important practical significance. At present, there are few efficient construction methods for this type of structure, which are mainly obtained by intermolecular and intramolecular tandem...

Claims

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Application Information

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IPC IPC(8): C07C303/40C07C311/51B01J31/24B01J31/02
CPCC07C303/40B01J31/2404B01J31/0227C07C2601/02C07C2601/10B01J2531/18C07C311/51
Inventor 王程宇韩玉管鹏程孔令凯
Owner LINYI UNIVERSITY
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