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Method for synthesizing 2, 3-disubstituted indanone derivative in water phase at one time

A one-time, two-substitution technology, applied in the direction of condensation to prepare carbonyl compounds, organic chemistry, etc., can solve the problem of limited application of disubstituted olefin substrates, and achieve the effects of wide expansion range, low toxicity and high yield

Active Publication Date: 2022-05-31
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004]However, the hydroacylation reaction requires complicated steps to prepare precursors for further cyclization, and the scope of substrates for disubstituted alkenes is very limited

Method used

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  • Method for synthesizing 2, 3-disubstituted indanone derivative in water phase at one time
  • Method for synthesizing 2, 3-disubstituted indanone derivative in water phase at one time
  • Method for synthesizing 2, 3-disubstituted indanone derivative in water phase at one time

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] [RhCl(cod)] 2 Catalyze the reaction of diphenylacetylene and 2-formylphenylboronic acid, the process is as follows:

[0030] Under nitrogen protection, [RhCl(cod)] was added sequentially in the reaction flask 2 5mol%, 0.15mmol of diphenylacetylene, 0.225mmol of 2-formylphenylboronic acid, 45μl of triethylamine, 0.5ml of water, and stirred at 50°C for 16h to obtain 42.1mg of the product with an isolated yield of 98%.

[0031] Characterize the product, the result is: 1 H NMR (400MHz, Chloroform-d) δ7.91(d, J=7.7Hz, 1H), 7.65(t, J=7.5Hz, 1H), 7.50(t, J=7.5Hz, 1H), 7.31(m ,J=12.1,7.0Hz,7H),7.12(t,J=7.0Hz,4H),4.60(d,J=4.8Hz,1H),3.83(d,J=4.8Hz,1H). 13 CNMR (151MHz, Chloroform-d) δ205.3, 156.2, 142.5, 138.5, 136.2, 135.5, 129.0, 128.9, 128.4, 128.3, 127.9, 127.2 (d, J=2.0Hz), 126.7, 124.1, 64.7, 54.9.

[0032] The product structure is:

[0033]

Embodiment 2

[0035] [RhCl(cod)] 2Catalyze the reaction of 1,2-bis(4-methylphenyl)acetylene with 2-formylphenylboronic acid, the process is as follows:

[0036] Under nitrogen protection, [RhCl(cod)] was added sequentially in the reaction flask 2 5mol%, 1,2-bis(4-methylphenyl)acetylene 0.15mmol, 2-formylphenylboronic acid 0.225mmol, triethylamine 45μl, water 0.5ml, stirred at 50°C for 16h to obtain 35.1mg of the product, separated Yield 75%.

[0037] Characterize the product, the result is: 1 H NMR (400MHz, Chloroform-d) δ7.89(d, J=7.7Hz, 1H), 7.63(t, J=7.5Hz, 1H), 7.48(t, J=7.4Hz, 1H), 7.31(d ,J=7.7Hz,1H),7.13(dd,J=8.1,2.3Hz,4H),7.00(dd,J=7.8,5.6Hz,4H),4.53(d,J=4.8Hz,1H),3.77 (d,J=4.8Hz,1H),2.34(d,J=4.4Hz,6H). 13 C NMR (151MHz, Chloroform-d) δ205.6, 156.4, 139.6, 136.8, 136.2, 135.6, 135.3, 129.6 (d, J=4.7Hz), 128.3, 128.2, 127.8, 126.7, 124.0, 64.4, 54.6, 21.1 (d ,J=5.6Hz).

[0038] The product structure is:

[0039]

Embodiment 3

[0041] [RhCl(cod)] 2 Catalyze the reaction of 1,2-bis(4-fluorophenyl)acetylene with 2-formylphenylboronic acid, the process is as follows:

[0042] Under nitrogen protection, [RhCl(cod)] was added sequentially in the reaction flask 2 5mol%, 1,2-bis(4-fluorophenyl)acetylene 0.15mmol, 2-formylphenylboronic acid 0.225mmol, triethylamine 45μl, water 0.5ml, stirred at 50°C for 16h to obtain 46.3mg of the product, isolated The rate is 96%.

[0043] Characterize the product, the result is: 1 H NMR (400MHz, Chloroform-d) δ7.89(d, J=7.7Hz, 1H), 7.66(t, J=7.5Hz, 1H), 7.51(t, J=7.5Hz, 1H), 7.29(d ,J=7.7Hz,1H),7.19-6.91(m,8H),4.50(d,J=5.2Hz,1H),3.73(d,J=5.2Hz,1H). 13 C NMR (101MHz, Chloroform-d) δ204.9, 162.2(d, J=247.4Hz), 162.1(d, J=247.1Hz), 155.6, 137.9(d, J=3.5Hz), 136.0, 135.8, 133.9(d ,J=3.5Hz),130.1(d,J=8.2Hz),129.5(d,J=8.3Hz),128.7,126.6,124.2,115.99(d,J=21.7Hz),115.98(d,J=21.6 Hz), 64.2, 54.4.

[0044] The product structure is:

[0045]

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Abstract

The invention discloses a method for one-time synthesis of a 2, 3-disubstituted indanone derivative in a water phase, and the method comprises the following steps: stirring a rhodium catalyst, triethylamine, internal alkyne and a 2-formyl phenylboronic acid mixture in water under an oxygen-free condition, and reacting to prepare the 2, 3-disubstituted indanone derivative. According to the method for synthesizing the 2, 3-disubstituted indanone derivative in the water phase at one time, exogenous ligands are not needed, the method is simple and easy to operate, only water is used as a solvent, and in the method, needed objects are small in toxicity, safe, environmentally friendly, high in product conversion rate and capable of being stored at the room temperature.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, and in particular relates to a method for one-time synthesis of 2,3-disubstituted indanone derivatives in an aqueous phase. Background technique [0002] Indanone derivatives widely exist in many natural products and biopharmaceuticals, and are often used as transformation intermediates in organic synthesis. Especially 2,3-disubstituted indanones show unique biological activity [P.-C.Huo, X.-Q.Guan, P.Liu, Y.-Q.Song, M.-R. Sun, R.-J.He, L.-W.Zou, L.-J.Xue, J.-H.Shi, N.Zhang, Z.-G.Liu and G.-B.Ge, Eur. J. Med. Chem., 2021, 209, 112856; S. Mozaffarnia, R. Teimuri-Mofrad and M.-R. Rashidi, Eur. J. Med. Chem., 2020, 191, 112140; Y. Yang, R .Zhang, Z.Li, L.Mei, S.Wan, H.Ding, Z.Chen, J.Xing, H.Feng, J.Han, H.Jiang, M.Zheng, C.Luo and B.Zhou, J. Med. Chem., 2020, 63, 1337]. For example, Pauciflorol F has potent anticancer properties and Pterosin B has anti-inflammatory activity. [0003] ...

Claims

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Application Information

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IPC IPC(8): C07C45/45C07C49/633C07C49/693C07C49/755
CPCC07C45/45C07C2602/08C07C49/633C07C49/693C07C49/755Y02P20/584
Inventor 薛飞赖静如吕平朱安侨
Owner NANJING FORESTRY UNIV
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