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A kind of 1,3-dihydroisobenzofuran derivative and its synthetic method and application

A technique for the synthesis of dihydroisobenzofuran, which is applied in the fields of organic chemistry, material excitation analysis, fluorescence/phosphorescence, etc., can solve the problems of limited substrates and cumbersome synthesis of raw materials, and achieve environmental friendliness, excellent yield, and Easy post-processing effects

Active Publication Date: 2022-08-02
QUFU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example: Literature [1] Shang, X.S.; Li, N.T.; Guo, Z.Q.; Liu, P.N. Dyes and Pigments 2016, 132, 167. [2] Sekine, K.; Takayanagi, A.; Kikuchi, S.; Yamada, T. Chem.Commun.2013,49,11320.[3]Zhang,W.-Z.; Yang,M.-W.;Yang,X.-T.;Shi,L.-L.;Wang,H.- B.; Lu, X.-B.Org.Chem.Front.2016, 3, 217. [4] Li, D.Y.; Shang, X.S.; Chen, G.R.; ] Li, D.Y.; Shi, K.J.; Mao, X.F.; Chen, G.R.; Liu, P.N.J.Org.Chem.2014, 79, 4602. Limited and other disadvantages

Method used

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  • A kind of 1,3-dihydroisobenzofuran derivative and its synthetic method and application
  • A kind of 1,3-dihydroisobenzofuran derivative and its synthetic method and application
  • A kind of 1,3-dihydroisobenzofuran derivative and its synthetic method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047]trans-2-((cis)-3-(cis)-benzylidene)isobenzofuran-1(trihydro)-methylene)-N-phenethyl-1-imine(IA) synthesis

[0048]

[0049] Under air (without inert gas protection), to a 10 mL vial, add ortho-phenylethynyl-substituted amine ketene (0.4 mmol), tetrahydrofuran (4 mL), tetrabutylammonium fluoride (0.08 mmol, 80 uL, 1 mol) / L in THF) was heated to 35°C and reacted for 2 hours to obtain the target product (IA) as a yellow solid, the isolated yield was 99%, mp: 106-108°C.

[0050] Product NMR data: 1 H NMR (500MHz, DMSO-d 6 ): δ8.80(d,J=9.5Hz,1H),8.09(d,J=7.8Hz,1H),8.00(d,J=7.8Hz,1H),7.85(d,J=7.5Hz,2H) ), 7.68-7.65(m, 1H), 7.61-7.58(m, 1H), 7.46-7.42(m, 4H), 7.30-7.23(m, 4H), 6.71(s, 1H), 6.59(d, J = 9.5Hz, 1H); 13 C NMR (125MHz, DMSO-d 6 ): δ159.74, 154.93, 152.26, 150.31, 134.34, 134.23, 131.65, 131.07, 130.02, 129.32, 128.98, 128.82, 127.19, 125.70, 121.91, 120.11, 120.4.9, 102

[0051] Product high-resolution mass spectrometry data: HRMS (ESI) calcd for C 23 H ...

Embodiment 2

[0053] trans-2-((cis)-3-(cis)-benzylidene)isobenzofuran-1(trihydro)-methylene)-N-p-methoxyphenethyl-1-imine Synthesis of (IB)

[0054]

[0055] Under air (without inert gas protection), to a 10 mL vial, add methoxy-substituted o-phenylethynylaminoketene (0.4 mmol), tetrahydrofuran (4 mL), tetrabutylammonium fluoride (0.04 mmol, 40uL, 1mol / L in THF) was heated to 35°C and reacted for 3 hours to obtain the target product (IB) as a yellow solid, the isolated yield was 99%, mp: 118-120°C.

[0056] Product NMR data: 1 H NMR (500MHz, DMSO-d 6 ): δ8.81(d,J=9.5Hz,1H),8.05(d,J=7.5Hz,1H),7.98(d,J=8.0Hz,1H),7.86(d,J=7.5Hz,2H) ),7.66-7.63(m,1H),7.60-7.55(m,1H),7.46-7.43(m,2H),7.30-7.26(m,3H),7.01-6.99(m,2H),6.68(s ,1H),6.55(d,J=9.5Hz,1H),3.79(s,3H); 13 C NMR (125MHz, DMSO-d 6 ): δ158.92,157.81,152.67,150.39,145.06,134.32,134.22,131.43,131.20,129.99,128.95,128.84,127.11,122.12,121.76,120.48,114.03,131.20,129.99,128.95,128.84,127.11,122.12,121.76,120.48,114.039,101

[0057] Produc...

Embodiment 3

[0059] trans-2-((cis)-3-(cis)-benzylidene)isobenzofuran-1(trihydro)-methylene)-N-p-chlorophenethyl-1-imine (IC )Synthesis

[0060]

[0061] Under air (without inert gas protection), to a 10 mL vial, add chlorine-substituted o-phenylethynylamine enone (0.4 mmol), tetrahydrofuran (4 mL), tetrabutylammonium bromide (abbreviation: TBAB, 0.08 mmol, 25.8 mg) and cesium fluoride (0.8 mmol, 121.5 mg) were heated to 35 °C and reacted for 2 hours to obtain the target product (IC) as a yellow solid, the isolated yield was 72%, mp: 149-451 °C.

[0062] Product NMR data: 1 H NMR (500MHz, DMSO-d 6 ): δ8.79(d,J=9.5Hz,1H),8.09(d,J=7.8Hz,1H),8.01(d,J=7.8Hz,1H),7.86(d,J=7.6Hz,2H) ), 7.69-7.66(m, 1H), 7.61-7.58(m, 1H), 7.48-7.43(m, 4H), 7.30-7.27(m, 3H), 6.72(s, 1H), 6.58(d, J = 9.5Hz, 1H); 13 C NMR (125MHz, DMSO-d 6 ): δ160.18, 155.71, 151.06, 150.27, 134.43, 134.17, 131.79, 131.00, 130.06, 129.88, 129.24, 129.07, 128.87, 127.26, 122.65, 122.37, 120.52, 102

[0063] Product high-resol...

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Abstract

The invention discloses a 1,3-dihydroisobenzofuran derivative of formula (I) and a synthesis method thereof. The amine ketene compound substituted by ortho-position alkynyl is used as a raw material, and under the action of a catalyst, the formula of formula (I) 1,3-dihydroisobenzofuran derivatives. The preparation method of the invention has the advantages of mild reaction conditions, insensitive reaction to air, simple and easy-to-obtain raw materials, good substrate universality, simple post-processing, excellent yield, environmental friendliness and the like. The present invention also provides the application of formula (I) 1,3-dihydroisobenzofuran derivatives in molecular fluorescent probes.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, in particular to a 1,3-dihydroisobenzofuran derivative, a synthesis method and application thereof. Background technique [0002] 1,3-Dihydroisobenzofuran compounds are an important class of organic compounds, which are the main structural units of many natural products and functional molecules, and can be used as intermediates in organic synthesis. Important application value, but there are few efficient construction methods for this type of structure. Therefore, more and more attention has been paid to the synthesis of 1,3-dihydroisobenzofuran compounds. For example, under the action of precious metals, bases and other salts, 1,3-dihydroisobenzofuran derivatives are obtained through multi-step synthesis. For example: Literature [1] Shang, X.S.; Li, N.T.; Guo, Z.Q.; Liu, P.N. Dyes and Pigments 2016, 132, 167. [2] Sekine, K.; Takayanagi, A.; Kikuchi, S.; Yamada, T. Chem. Commun. 2013,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/87G01N21/64
CPCG01N21/64C07D307/87
Inventor 赵育磊张正王宗康司志姚傅德斌刘旭郑丽君李曼李慧婷孟占乾刘璐李瑞吴楠
Owner QUFU NORMAL UNIV