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Polysubstituted beta-phenylallyl alcohol compound as well as synthesis method and application thereof

A phenylpropenyl alcohol, multi-substitution technology, which is applied to the effective components of hydroxyl compounds, carbon-based compound preparation, chemical instruments and methods, etc., can solve the problems such as the activity of multi-substituted β-phenylpropenyl alcohol compounds that have not been reported in the literature

Active Publication Date: 2020-10-27
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] At present, there is no literature reporting the activity of multi-substituted β-phenylpropenyl alcohols in the treatment of diabetes and cancer

Method used

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  • Polysubstituted beta-phenylallyl alcohol compound as well as synthesis method and application thereof
  • Polysubstituted beta-phenylallyl alcohol compound as well as synthesis method and application thereof
  • Polysubstituted beta-phenylallyl alcohol compound as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083]

[0084] The dry reaction tube was wrapped in aluminum foil to avoid light, and AgBF was added in the glove box 4 (29.8mg, 0.15mmol), after removing from the glove box, add [Cp*RhCl 2 ] 2 (15.5 mg, 0.025 mmol), NaOAc (16.7 mg, 0.20 mmol), 3-methoxyphenylboronic acid (2a, 228.5 mg, 1.5 mmol), 1a (139.7 mg, 1.0 mmol), MeOH (5 mL). The reaction tube is filled with CaCl 2 Open the drying tube to the atmosphere and stir at room temperature for 40 minutes. The reaction solution was filtered through a diatomaceous earth short column (3 cm), washed with MeOH, and the solvent was removed by rotary evaporation. Separation and purification were carried out by silica gel column chromatography (eluent: petroleum ether / ethyl acetate = 10 / 1) to obtain product E-3aa (211.1 mg, 85%): pale yellow liquid; 1 H NMR (400MHz, CDCl 3 )δ=7.22(t, J=8.0Hz, 1H, ArH), 6.89(d, J=8.0Hz, 1H, ArH), 6.86-6.82(m, 1H, ArH), 6.79(dd, J 1 =7.8Hz,J 2 =2.6Hz, 1H, ArH), 5.70(s, 1H, =CH), 3.81(s, 3H, ...

Embodiment 2

[0086]

[0087] The dry reaction tube was wrapped in aluminum foil to avoid light, and AgBF was added in the glove box 4 (29.5mg, 0.15mmol), after removing from the glove box, add [Cp*RhCl 2 ] 2 (15.8 mg, 0.025 mmol), NaOAc (16.5 mg, 0.20 mmol), 4-formylphenylboronic acid (2b, 229.6 mg, 1.5 mmol), 1a (140.6 mg, 1.0 mmol), MeOH (5 mL), at room temperature Stir for 4 hours. The reaction solution was filtered through a diatomaceous earth short column (3 cm), washed with MeOH, and the solvent was removed by rotary evaporation. Separation and purification were carried out by silica gel column chromatography (eluent: separation by column chromatography for the first time: petroleum ether, petroleum ether / ethyl acetate=30 / 1-10 / 1, to obtain 94.6 mg of pure product and 109.4 mg of impure product ; The impure product was separated by column chromatography for the second time: dichloromethane, to obtain 91.7 mg of pure product), to obtain product E-3ab (186.3 mg, 75%): yellow liqui...

Embodiment 3

[0089]

[0090] Operation is with embodiment 1. ikB 4 (29.0mg, 0.15mmol), [Cp*RhCl 2 ] 2 (15.8 mg, 0.025 mmol), NaOAc (17.3 mg, 0.20 mmol), 4-fluorophenylboronic acid (2c, 210.3 mg, 1.5 mmol), 1a (139.4 mg, 1.0 mmol), MeOH (5 mL), reacted for 19 hours to obtain E-3ac (130.7 mg, 56%) (crude spectrum shows 15% of raw material remaining) (eluent: toluene): pale yellow liquid; 1 H NMR (400MHz, CDCl 3 )δ=7.31-7.20(m, 2H, ArH), 7.04-6.92(m, 2H, ArH), 5.64(s, 1H, =CH), 2.78(t, J=7.6Hz, 2H, CH 2 ), 1.61(brs, 1H, OH), 1.46(s, 6H, 2x CH 3 ), 1.36-1.18 (m, 4H, 2x CH 2 ), 0.84(t, J=7.0Hz, 3H, CH 3 ); 13 C NMR (100MHz, CDCl 3 ,) δ = 161.9 (d, J = 243.6Hz), 142.1, 139.7 (d, J = 3.0Hz), 135.8, 128.1 (d, J = 7.6Hz), 114.9 (d, J = 20.5Hz), 71.3, 31.6, 31.0, 29.8, 22.9, 13.9; 19 F NMR (376MHz, CDCl 3 )δ=-116.8; IR (neat): v=3357, 2961, 2928, 2861, 1637, 1601, 1506, 1465, 1362, 1220, 1157, 1106, 1014cm -1 ; MS (70eV, EI) m / z (%): 236 (M + , 4.74), 109(100); HRMS calcd for C 15 ...

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Abstract

The invention discloses a synthesis method of a polysubstituted beta-phenylallyl alcohol compound, and the method comprises the following steps: reacting polysubstituted propargyl alcohol with organicboric acid in an organic solvent under the actions of a rhodium catalyst, alkali and silver salt to directly construct the polysubstituted beta-phenylallyl alcohol compound in one step. The method issimple to operate, raw materials and reagents are easy to obtain, reaction conditions are mild, substrate universality is wide, functional group compatibility is good, and the reaction has high regioselectivity and stereoselectivity (single configuration). According to the method disclosed by the invention, the polysubstituted beta-phenylallyl alcohol compound can be directly obtained without using a protecting group. The invention also discloses application of the polysubstituted beta-phenylallyl alcohol compound in preparation of drugs for treating and / or preventing diabetes mellitus and antitumor drugs.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a multi-substituted β-phenylpropenyl alcohol compound, its synthesis method and its medical application. [0002] technical background [0003] Stereoselective olefinic structures widely exist in natural products, drug molecules, and advanced materials, and are an important class of organic building blocks (Ref: (a) Oger, C.; Balas, L.; Durand, T.; Galano, J.-M.Chem.Rev.2013, 113, 1313.(b) Negishi, E.-i.; Huang, Z.; Wang, G.; Mohan, S.; Wang, C.; Hattori, H. Acc.Chem.Res.2008, 41, 1474.(c) Flynn, A.B.; Ogilvie, W.W.Chem.Rev.2007, 107, 4698.(d) Mori, M.Eur.J.Org.Chem. , 4981. (e) Shindo, M.; Matsumoto, K. Top. Curr. Chem. 2012, 327, 1. (f) Paek, S.-M. Molecules 2012, 17, 3348. (g) He, Z .;Kirchberg, S.; hlich, R.; Studer, A.Angew.Chem.Int.Ed.2012, 51, 3699. (h) Barczak, N.T.; Rooke, D.A.; Menard, Z.A.; , 52, 7579.). Some cis-trans isomers of alkenes may...

Claims

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Application Information

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IPC IPC(8): C07C43/23C07C41/30C07C47/56C07C45/68C07C33/48C07C29/32C07C33/28C07C205/19C07C201/12C07C255/37C07C253/30C07C35/21C07C69/92C07C67/343C07D303/14C07C43/215C07C255/53C07C35/17C07C39/21C07D333/16A61K31/085A61K31/11A61K31/045A61K31/277A61K31/235A61K31/336A61K31/05A61K31/381A61P3/10A61P35/00A61P35/02
CPCC07C43/23C07C47/56C07C33/483C07C33/28C07C205/19C07C255/37C07C35/21C07C69/92C07D303/14C07C43/215C07C255/53C07C35/17C07C39/21C07D333/16A61P3/10A61P35/00A61P35/02C07C2601/14Y02P20/55
Inventor 麻生明王维一陈勤钱辉
Owner FUDAN UNIV
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