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O-hydroxy-nitrogen silane compound and synthesis method thereof

A synthesis method and compound technology, applied in the direction of silicon organic compounds, dyed organosilicon compound treatment, organic chemical methods, etc., can solve the problems of inability to protect hydroxyl groups, restrict the universality of substrates, increase the energy consumption of synthesis processes, etc., and reach the price Inexpensive, simple and efficient synthesis method, and the effect of improving synthesis efficiency

Active Publication Date: 2020-11-27
WUYI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the use of palladium catalysts in the current synthetic methods requires the participation of multiple reactants (Chemistry-A European Journal. 2014, 30, 9250), while the use of other existing catalytic systems requires multiple steps, and cannot protect Hydroxyl (Catalysis Science&Technology.2014, 11, 3964), which restricts the universality of the substrate and increases the energy consumption of the synthesis process

Method used

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  • O-hydroxy-nitrogen silane compound and synthesis method thereof
  • O-hydroxy-nitrogen silane compound and synthesis method thereof
  • O-hydroxy-nitrogen silane compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1: the preparation of 2-((phenyl (triethylsilyl) amino) methyl) phenol

[0041]

[0042] In a 15mL reaction tube, sequentially add salicylidene aniline (98mg, 0.5mmol), triethylsilane (116mg, 1.0mmol), tris(triphenylphosphine)carbonyl ruthenium hydrochloride (23.8mg, 0.025mmol) , under the conditions of toluene (2 mL) and nitrogen, the reaction temperature was 120 ° C under electromagnetic stirring reaction, and the reaction time was 8 hours. After the reaction was completed, the solvent was removed by rotary evaporation, and the mixture was separated by column chromatography. The eluents were ethyl acetate and petroleum ether (ethyl acetate: petroleum ether = 1:10). After separation, a yellow oil body (138 mg, 88%).

[0043] The product detection data are as follows:

[0044] 1 H NMR (300MHz, CDCl 3) δ = 7.36-7.16 (m, 4H), 6.97-6.67 (m, 5H), 4.36 (s, 2H), 1.05 (t, 9H, J = 8.1 Hz), 0.88-0.80 (m, 6H).

[0045] 13 C NMR (75MHz, CDCl 3 ) δ = 153.9, 148...

Embodiment 2

[0046] Example 2: 2-((((4-fluorophenyl)(triethylsilyl)amino)methyl)phenol

[0047]

[0048] In a 15mL reaction tube, sequentially add 4-fluoro-N-o-hydroxybenzylidene aniline (165mg, 0.5mmol), triethylsilane (116mg, 1.0mmol), tris(triphenylphosphine)carbonyl hydrochloride Ruthenium (23.8 mg, 0.025 mmol) was reacted under toluene (2 mL) and nitrogen under electromagnetic stirring at a reaction temperature of 120° C., and the reaction time was 8 hours. After the reaction was completed, the solvent was removed by rotary evaporation, and the mixture was separated by column chromatography. The eluent was ethyl acetate and petroleum ether (ethyl acetate: petroleum ether = 1:10), and a light yellow oil (85mg , 51%).

[0049] The product detection data are as follows:

[0050] 1H NMR (500MHz, CDCl3) δ=7.34-7.32(d, 1H, J=7.5Hz), 7.21-7.17(m, 1H), 7.03-6.99(m, 2H), 6.98-6.94(m, 1H), 6.88-6.76(m,1H),6.74-6.73(m,1H),6.67-6.62(m,1H),4.39(s,2H),1.06-1.03(m,9H),0.85-0.83(m,6H ).

[00...

Embodiment 3

[0052] Example 3: 2-((((4-bromophenyl)(triethylsilyl)amino)methyl)phenol

[0053]

[0054] In a 15mL reaction tube, sequentially add 4-bromo-N-o-hydroxybenzylidene aniline (137mg, 0.5mmol), triethylsilane (116mg, 1.0mmol), tris(triphenylphosphine)carbonyl hydrochloride Ruthenium (23.8 mg, 0.025 mmol) was reacted under toluene (2 mL) and nitrogen under electromagnetic stirring at a reaction temperature of 120° C., and the reaction time was 8 hours. After the reaction was completed, the solvent was removed by rotary evaporation, and the mixture was separated by column chromatography. The eluents were ethyl acetate and petroleum ether (ethyl acetate: petroleum ether = 1:10). After separation, a yellow oil body (170 mg, 87%).

[0055] The product detection data are as follows:

[0056] 1 H NMR (500MHz, CDC1 3 )δ=7.32-7.28(m,3H),7.23-7.21(t,1H,J=7.5Hz),6.98-6.95(t,1H,J=7Hz),6.90-6.89(d,1H,J=8Hz ), 6.56-6.55 (t, 2H, J=4.5Hz), 4.33 (s, 2H), 1.08-1.05 (m, 9H), 0.88-0.83 (m, 6H...

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Abstract

The invention discloses an o-hydroxy-nitrogen silane compound and a synthesis method thereof. The o-hydroxy-nitrogen silane compound has a chemical general formula shown in the specification, and in the formula, Y1-Y9 are independently selected from a hydrogen atom, a halogen atom, C1-22 alkyl, C1-22 haloalkyl, a hydroxyl group, an amino group, a carbonyl group, an amino group, a carboxyl group, an ester group, a cyano group, a phenyl group, a benzyl group or a nitro group, R1 is selected from C1-22 alkyl. The synthesis method comprises the following steps of: carrying out a reaction on a salicylideneaniline compound shown as a formula II and an alkyl silicon compound shown as a formula III as reaction raw materials under the existence of a ruthenium catalyst and a solvent and under a heating condition to obtain the o-hydroxy-nitrogen silane compound shown as a formula I, and the reaction formula is shown in the specification, wherein in the formula, R1 is selected from C1-22 alkyl.

Description

technical field [0001] The invention relates to the technical field of organic chemistry, in particular to an o-hydroxy-nitrosilane compound and a synthesis method thereof. Background technique [0002] Organosilicon compounds are valuable synthetic intermediates in various organic reactions and have diverse potential uses in materials science. In addition, there have been increasing reports in the literature recently about the use of organosilicon compounds as therapeutically relevant molecules, such as amilotide, phthalic acid, silicon-containing analogues of tetrahydroisoquinoline, silapropin, and TMS- Application of alanine in medicinal chemistry (J.Am.Chem.Soc.2009,131,8350-8351; Chem.Soc.Rev.2009,38,1002-1010; J.Med.Chem.2013,56,388- 405). [0003] Due to the potential biological activity of organosilicon compounds, they can be used as potential drug molecules in antihypertensive, antitumor, antidepressant and other fields, so they have attracted widespread attention...

Claims

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Application Information

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IPC IPC(8): C07F7/10C07F7/08C07B47/00C09C1/28C09C1/36C09C3/12G03F7/004
CPCC07F7/10C07F7/0814C07B47/00C09C1/28C09C1/36C09C3/12G03F7/004
Inventor 李滨林子睿黄小敏
Owner WUYI UNIV
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