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Preparation and application of 1,7-disubstituted aminomethyl-2,8-dyhydroxy-Troger's Base catalyst

A -base, aminomethyl technology, applied in the field of organic synthesis, can solve problems such as no literature reports

Active Publication Date: 2019-02-05
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Catalyzed synthesis of pyran ring derivatives using TB catalysts has not been reported in the literature

Method used

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  • Preparation and application of 1,7-disubstituted aminomethyl-2,8-dyhydroxy-Troger's Base catalyst
  • Preparation and application of 1,7-disubstituted aminomethyl-2,8-dyhydroxy-Troger's Base catalyst
  • Preparation and application of 1,7-disubstituted aminomethyl-2,8-dyhydroxy-Troger's Base catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1: preparation compound 3a

[0043] Add formaldehyde (1.2mmol), cyclohexylamine (1.2mmol), glacial acetic acid (1mol%) and ethanol (3mL) successively into a 50mL dry round-bottomed flask. mmol), followed by TLC until the reaction was complete, the excess solvent was evaporated under reduced pressure, and recrystallized (EtOH) to obtain compound 3a with a yield of 83%.

[0044] The structural formula of compound 3a is:

[0045] The molecular formula is: C 29 h 40 N 4 o 2

[0046]The Chinese name is: 1,7-bis((cyclohexylamino)methyl)-6H, 12H--5,11-methanodibenzo[b,f] [1,5] diazocine-2,8- diol

[0047] The English name is:

[0048] 1,7-Bis((cyclohexylamino)methyl)-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine-2,8-diol

[0049] Appearance: white solid

[0050] Melting point: 153.5-154.2°C

[0051] Proton NMR spectrum: 1 H NMR (400MHz, CDCl 3 )δ6.95(d, J=8.8Hz, 2H), 6.66(d, J=8.8Hz, 2H), 4.89(d, J=9.4Hz, 1H), 4.81(d, J=10.0Hz, 1H) ,4.44(d,J=16.6Hz,2...

Embodiment 2

[0054] Embodiment 2: preparation compound 3b

[0055] Add formaldehyde (1.2mmol), methylamine (1.2mmol), glacial acetic acid (1mol%) and ethanol (3mL) successively into a 50mL dry round bottom flask, and after reflux reaction at 80°C for 2h, add intermediate 2 (1.0mmol ), followed by TLC until the reaction was complete, the excess solvent was evaporated under reduced pressure, and recrystallized (EtOH) to obtain compound 3b with a yield of 87%.

[0056] The structural formula of compound 3b is:

[0057] The molecular formula is: C 19 h 24 N 4 o 2

[0058] The Chinese name is: 1,7-bis((methylamino)methyl)-6H, 12H--5,11-methanodibenzo [1,5] diazocine-2,8- diol

[0059] The English name is:

[0060] 1,7-Bis((methylamino)methyl)-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine-2,8-diol

[0061] Appearance: white solid

[0062] Melting point: 244.3-247.1°C

[0063] Proton NMR spectrum: 1 H NMR (400MHz, CDCl3) δ6.97(d, J=8.8Hz, 2H), 6.71(d, J=8.8Hz, 2H), 4.67(s, 4H), 4.42...

Embodiment 3

[0066] Embodiment 3: preparation compound 3c

[0067] Formaldehyde (1.2mmol), n-butylamine (1.2mmol), glacial acetic acid (1mol%) and ethanol (3mL) were added successively to a 50mL dry round bottom flask, and intermediate 2 (1.0 mmol), followed by TLC until the reaction was complete, the excess solvent was evaporated under reduced pressure, and recrystallized (EtOH) to obtain compound 3c with a yield of 85%.

[0068] The structural formula of compound 3c is:

[0069] The molecular formula is: C 25 h 36 N 4 o 2

[0070] Chinese name: 1,7-bis((butylamino)methyl)-6H, 12H--5,11-methanodibenzo [b, f] [1,5] diazocine-2,8- diol

[0071] The English name is:

[0072] 1,7-Bis((butylamino)methyl)-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine-2,8-diol

[0073] Appearance: white solid

[0074] Melting point: 159.3-161.9°C

[0075] Proton NMR spectrum: 1 H NMR (400MHz, CDCl 3 )δ6.95(d, J=8.8Hz, 2H), 6.68(d, J=8.8Hz, 2H), 4.74(d, J=2.4Hz, 4H), 4.42(d, J=16.8Hz, 2H) ,4.22(s,...

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Abstract

The invention discloses preparation and application of 1,7-disubstituted aminomethyl-2,8-dyhydroxy-Troger's Base catalyst. P-methoxyaniline and paraformaldehyde are taken as raw materials and are subjected to reaction including hydrolysis, Mannich and the like to synthesize the 1,7-disubstituted aminomethyl-2,8-dyhydroxy-Troger's Base catalyst base derivative; the compound is taken as catalyst tocatalyze addition reaction taking 4-hydroxycoumarin and benzyl cyanide as raw materials, and one series of pyranoid ring derivative is synthesized. According to the invention, the substrate range of the pyranoid ring derivative is widened, and the application range of TB on the aspect of catalysis is widened.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and relates to a Base catalyst, especially a kind of 1,7-disubstituted aminomethyl-2,8-dihydroxy- Base catalyst preparation and application. Background technique [0002] The pyran ring is an important part of many natural compounds with biological activity, such as alkaloids, vitamin E, flavonoids and anthocyanins, etc. Although pyran ring derivatives are very useful in medicine, their synthetic methods are still difficult to carry out. [0003] Coumarin is a class of compounds containing a pyrone skeleton, which is the basic skeleton of important plant secondary metabolites flavonoids, and has a wide range of pharmacological activities, such as anti-inflammatory, anti-tuberculosis, antioxidant, antiviral, antibacterial, Anti-cancer, anti-depression, anti-hyperlipidemia, etc. Therefore, the synthesis of pyran ring derivatives from coumarin compounds has certain medical value. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/08B01J31/02C07D491/153C07D491/22A61P31/04
CPCA61P31/04B01J31/0271C07D487/08C07D491/153C07D491/22
Inventor 陈雯苑睿崔浩任璇璇周生亮宛瑜吴翚
Owner XUZHOU NORMAL UNIVERSITY
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