CN108658846A - Quaternary amine of the group containing anacardol and application thereof - Google Patents
Quaternary amine of the group containing anacardol and application thereof Download PDFInfo
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- CN108658846A CN108658846A CN201810600936.6A CN201810600936A CN108658846A CN 108658846 A CN108658846 A CN 108658846A CN 201810600936 A CN201810600936 A CN 201810600936A CN 108658846 A CN108658846 A CN 108658846A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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Abstract
The present invention relates to quaternary amines of a kind of group containing anacardol and application thereof.The quaternary amine is compound shown in Formulas I.Quaternary amine provided by the invention can be used as the application of the cationic surfactant with resisting gram-positive bacteria.In Formulas I, R1Linear or branched alkyl group or halogenated carbon atom for carbon atom more than or equal to four are greater than or equal to four linear or branched alkyl group；R2For C15Chain alkyl；X is halogen.
Description
Technical field
The present invention relates to quaternary amines of a kind of group containing anacardol and application thereof, specifically, being related to a kind of containing anacardol
Asymmetric double stroma quaternary amine of group and application thereof.
Background technology
Anacardol is a kind of plant or paddy purified from cashew nut shell oil (Cashew Nut Shell Liquid, CNSL)
Material resource renewable raw materials.Anacardol includes four kinds of different meta position alkyl phenols.Due to having on four kinds of monomer molecules of anacardol
A variety of functional groups that can be used for chemical derivatization：Carbon-carbon double bond on phenolic hydroxyl group, phenyl ring and carbon long-chain, anacardol are one non-
Often with the molecular structure for having derivative potentiality.
This research group is once C with meta position15Chain alkyl anacardol by the chain alkyl of certain length with containing N's
Aromatic compound is connected, and obtains a kind of Cardanol derivative of structure novel, can be used as cationic surfactant use
(CN 107892671A)。
With going deep into for research, the inventors found that：Through appropriate chemical modification can be obtained it is a kind of based on bipyridyl,
And the asymmetric double stroma quaternary amine of the group containing anacardol.Obtained asymmetric double stroma quaternary amine can be used as cation
Surfactant uses, and with excellent antibacterial (especially gram positive bacterial strain) performance.
Invention content
It is an advantage of the invention to provide a kind of quaternary amines of the group containing anacardol of structure novel.
Quaternary amine of the present invention is compound shown in Formulas I：
In Formulas I, R1It is linear or branched alkyl group or the halogen (F, Cl, Br or/and I, similarly hereinafter) that carbon atom is greater than or equal to four
The carbon atom in generation is greater than or equal to four linear or branched alkyl group；R2For C15Chain alkyl；X be halogen (F, Cl, Br or I, under
Together).
Another object of the present invention is, discloses a kind of purposes of above-mentioned quaternary amine.I.e. compound shown in Formulas I is used as and has
The application of the cationic surfactant of resisting gram-positive bacteria.
In addition, a further object of the invention is, method that compound shown in a kind of formula I is provided.The method
Include the following steps：
(1) by 4,4 '-bipyridylsWith alkyl halide (R1X it) reacts, prepares intermediate AThe step of；
(2) by anacardolWith halogenated hydrocarbonsReaction prepares intermediate B
The step of；With,
(3) the step of being reacted with intermediate B by intermediate A, preparing object (compound shown in Formulas I).
Its synthetic route is as follows：
Wherein, R1,R2With the meaning of X with it is described previously identical.
Specific implementation mode
In an optimal technical scheme of the invention, R1For C4~C14Linear or branched alkyl group or halogenated C4~C14
Linear or branched alkyl group；
Further preferred technical solution is：R1For C4~C14Straight chained alkyl.
In presently preferred technical solution, R2For C15Straight chained alkyl.
Present invention will be further explained below with reference to specific examples.It should be understood that these embodiments are only used for understanding this hair
It is bright, rather than limit the scope of the invention.
Embodiment 1
Formulas IAThe preparation of shown compound：
By 4,4'-Bipyridine (15mmol, 5equiv), bromination of n-butane (3mmol, 1equiv) is dissolved in anhydrous acetonitrile,
It is placed in the reaction through Non-aqueous processing, under argon gas protection, 82 DEG C are reacted 24 hours, and anhydrous acetonitrile is spin-dried for.With methanol/acetic acid second
Ester is that recrystallization solvent is recrystallized, and obtains intermediate A-A；
- two bromo- 2- butylene (30mmol, 3equiv) of trans- Isosorbide-5-Nitrae is dissolved in acetone, addition Anhydrous potassium carbonate (60mmol,
6equiv), it stirs 30 minutes；Separately anacardol (10mmol, 1equiv) is dissolved in acetone, obtains clear solution.It is dripped with constant pressure
Liquid funnel instills at a slow speed anacardol acetone soln in the acetone soln of trans-1,4-dibromo-2-butylene.Stirring 30 minutes.It will be anti-
It answers system to be heated to 56 DEG C, reacts 24 hours, filtering, dry sample processed, pure petroleum ether crosses column, obtains intermediate B-A；
Intermediate A-A (1mmol, 1equiv) and intermediate B-A (1.2mmol, 1.2equiv) are dissolved in anhydrous acetonitrile,
It being placed in the reaction through Non-aqueous processing, under argon gas protection, 82 DEG C are reacted 24 hours, are cooled to room temperature, and suction filtration obtains solid, and
Solid (3 × 15mL) is washed with acetonitrile, obtains beige solid (Formulas IAShown compound).
1H NMR(400MHz,CD3OD):δ 9.29-9.30 (d, J=4.0Hz, 2H), 9.25-9.27 (d, J=8.0Hz,
2H),8.69-8.71(m,4H),7.14-7.18(m,1H),6.73-6.78(m,3H),6.23-6.44(m,2H),5.43-5.45
(d, J=8.0Hz, 2H), 4.74-4.78 (t, J=8.0Hz, 2H), 4.66-4.67 (d, J=4.0Hz, 2H), 2.54-2.58
(t, J=8.0Hz, 2H), 2.04-2.12 (m, 2H), 1.55-1.62 (m, 2H), 1.28-1.31 (m, 24H), 1.02-1.06 (t,
J=8.0Hz, 3H), 0.88-0.91 (t, J=6.0Hz, 3H)；
13C NMR(101MHz,CD3OD):δ159.77,151.69,145.88,137.49,130.35,128.38,
124.44,122.43,121.36,115.98,112.71,67.78,63.96,63.12,36.95,34.50,32.67,30.76,
30.48,30.36,23.75,20.50,14.46,13.79.
HRMS(ESI-TOF)m/z:[M-2Br]2+Theoretical value (Calcd for) C39H58N2O 285.2269；Experiment value
(Found)285.2271.
Embodiment 2
Formulas IBThe preparation of shown compound：
Divided by bromo n-hexane alternative embodiment 1 outside bromination of n-butane, other Step By Conditions are same as Example 1,
Obtain Formulas IBShown compound (beige solid).
1H NMR(400MHz,CD3OD):δ 9.28-9.30 (d, J=8.0Hz, 2H), 9.25-9.27 (d, J=8.0Hz,
2H),8.69-8.70(m,4H),7.14-7.18(m,1H),6.73-6.78(m,3H),6.23-6.44(m,2H),5.43-5.44
(d, J=4.0Hz, 2H), 4.74-4.77 (t, J=6.0Hz, 2H), 4.66-4.67 (d, J=4.0Hz, 2H), 2.54-2.58
(t, J=8.0Hz, 2H), 2.06-2.13 (m, 2H), 1.55-1.62 (m, 2H), 1.28-1.47 (m, 30H), 0.88-0.95 (m,
6H)；
13C NMR(101MHz,CD3OD):δ159.77,151.69,145.88,137.49,130.35,128.37,
124.44,122.43,121.20,115.98,112.70,67.77,63.97,63.34,36.95,33.09,32.66,32.56,
30.76,30.48,30.36,26.93,23.75,23.52,14.45,14.28.
HRMS(ESI-TOF)m/z:[M-2Br]2+Calcd for C41H62N2O 299.2426；Found 299.2419.
Embodiment 3
Formulas ICThe preparation of shown compound：
Divided by n-octane bromide alternative embodiment 1 outside bromination of n-butane, other Step By Conditions are same as Example 1,
Obtain Formulas ICShown compound (beige solid).
1H NMR(400MHz,CD3OD):δ 9.29-9.30 (d, J=4.0Hz, 2H), 9.25-9.27 (d, J=8.0Hz,
2H),8.69-8.71(m,4H),7.14-7.18(m,1H),6.73-6.78(m,3H),6.23-6.44(m,2H),5.43-5.45
(d, J=8.0Hz, 2H), 4.74-4.77 (t, J=6.0Hz, 2H), 4.66-4.67 (d, J=4.0Hz, 2H), 2.54-2.57
(t, J=6.0Hz, 2H), 2.06-2.13 (m, 2H), 1.55-1.62 (m, 2H), 1.28-1.44 (m, 34H), 0.88-0.92 (m,
6H)；
13C NMR(101MHz,CD3OD):δ159.77,151.69,145.88,137.49,130.35,128.38,
124.45,122.43,121.63,115.99,112.71,67.78,63.96,63.36,36.95,33.09,32.90,32.66,
32.61,30.76,30.48,30.36,30.14,27.26,23.75,23.68,14.46,14.41.
HRMS(ESI-TOF)m/z:[M-2Br]2+Calcd for C43H66N2O 313.2582；Found 313.2589.
Embodiment 4
Formulas IDThe preparation of shown compound：
Divided by bromo n-decane alternative embodiment 1 outside bromination of n-butane, other Step By Conditions are same as Example 1,
Obtain Formulas ICShown compound (beige solid).
1H NMR(400MHz,CD3OD):δ 9.29-9.30 (d, J=4.0Hz, 2H), 9.25-9.27 (d, J=8.0Hz,
2H),8.69-8.71(m,4H),7.14-7.18(m,1H),6.73-6.77(m,3H),6.23-6.45(m,2H),5.43-5.45
(d, J=8.0Hz, 2H), 4.74-4.77 (t, J=6.0Hz, 2H), 4.66-4.67 (d, J=4.0Hz, 2H), 2.54-2.57
(t, J=6.0Hz, 2H), 2.06-2.13 (m, 2H), 1.53-1.61 (m, 2H), 1.27-1.44 (m, 38H), 0.87-0.91 (t,
J=8.0Hz, 6H)；
13C NMR(101MHz,CD3OD):δ159.77,151.27,145.87,137.49,130.35,128.39,
124.46,122.42,121.42,116.00,112.71,67.79,63.95,63.37,36.96,33.09,33.05,32.67,
32.61,30.77,30.62,30.55,30.42,30.18,27.27,23.71,14.44.
HRMS(ESI-TOF)m/z:[M-2Br]2+Calcd for C45H70N2O 327.2738；Found 327.2732.
Embodiment 5
Formulas IEThe preparation of shown compound：
Divided by bromododecane alternative embodiment 1 outside bromination of n-butane, other Step By Conditions are same as Example 1,
Obtain Formulas IEShown compound (beige solid).
1H NMR(400MHz,CD3OD):δ 9.28-9.30 (d, J=8.0Hz, 2H), 9.25-9.27 (d, J=8.0Hz,
2H),8.68-8.71(m,4H),7.14-7.18(m,1H),6.73-6.78(m,3H),6.24-6.43(m,2H),5.43-5.45
(d, J=8.0Hz, 2H), 4.73-4.77 (t, J=8.0Hz, 2H), 4.66-4.67 (d, J=4.0Hz, 2H), 2.54-2.57
(t, J=6.0Hz, 2H), 2.06-2.13 (m, 2H), 1.55-1.62 (m, 2H), 1.28-1.44 (m, 42H), 0.87-0.91 (t,
J=8.0Hz, 6H)；
13C NMR(101MHz,CD3OD):δ159.77,151.29,145.88,137.49,130.35,129.85,
124.45,122.43,115.96,112.70,67.78,63.96,63.37,36.95,33.08,32.67,32.61,30.76,
30.48,30.36,30.18,27.27,23.75,14.45.
HRMS(ESI-TOF)m/z:[M-2Br]2+Calcd for C47H74N2O 341.2895；Found 341.2908.
Embodiment 6
Formulas IFThe preparation of shown compound：
Divided by bromotetradecane alternative embodiment 1 outside bromination of n-butane, other Step By Conditions are same as Example 1,
Obtain Formulas IFShown compound (beige solid).
1H NMR(400MHz,CD3OD):δ 9.28-9.30 (d, J=8.0Hz, 2H), 9.25-9.27 (d, J=8.0Hz,
2H),8.69-8.71(m,4H),7.14-7.18(m,1H),6.73-6.77(m,3H),6.23-6.44(m,2H),5.43-5.45
(d, J=8.0Hz, 2H), 4.74-4.77 (t, J=6.0Hz, 2H), 4.66-4.67 (d, J=4.0Hz, 2H), 2.53-2.57
(t, J=8.0Hz, 2H), 2.06-2.13 (m, 2H), 1.55-1.62 (m, 2H), 1.28-1.44 (m, 46H), 0.87-0.91 (t,
J=8.0Hz, 6H)；
13C NMR(101MHz,CD3OD):δ159.77,151.27,145.87,137.48,130.35,128.39,
124.46,122.42,121.42,116.00,112.70,67.78,63.95,63.36,36.96,33.09,32.68,32.62,
30.78,30.37,30.19,27.27,23.76,14.46.
HRMS(ESI-TOF)m/z:[M-2Br]2+Calcd for C49H78N2O 355.3052；Found 355.3042.
Embodiment 7
Formulas IGThe preparation of shown compound：
Divided by perfluoro butyl ethyl iodide alternative embodiment 1 outside bromination of n-butane, other Step By Conditions and 1 phase of embodiment
Together, Formulas I is obtainedGShown compound (beige solid).
1H NMR(400MHz,CD3OD):δ 9.42-9.43 (d, J=4.0Hz, 2H), 9.26-9.28 (d, J=8.0Hz,
2H), 8.75-8.77 (d, J=8.0Hz, 2H), 7.14-7.18 (m, 1H), 6.73-6.78 (m, 3H), 6.24-6.45 (m, 2H),
5.43-5.45 (d, J=8.0Hz, 2H), 4.66-4.67 (d, J=4.0Hz, 2H), 3.18-3.27 (m, 2H), 2.54-2.58
(t, J=8.0Hz, 2H), 1.55-1.62 (m, 2H), 1.28-1.31 (m, 24H), 0.88-0.91 (t, J=4.0Hz, 3H)；
13C NMR(101MHz,CD3OD):δ159.76,151.40,145.58,142.64,130.35,128.59,
126.55,124.39,122.43,120.68,118.70,118.63,115.98,112.69,111.53,67.76,64.01,
62.83,36.96,33.09,32.68,30.77,30.49,30.37,24.55,23.76,14.46.
HRMS(ESI-TOF)m/z:[M-I-Br]2+Calcd for C41H53F9N2O 380.2002；Found
380.1995.
Embodiment 8
Compound IA-IGThe test of surface property
Due to compound IA-IGSolubility property have differences, we are classified as two groups.First group of (compound IAWith
IB), second group of (compound IC-IG), its surface property is tested respectively.
First group of (compound IAAnd IB) the specific test method is as follows：
The compound I of a concentration of 0.001mol/L is respectively configuredAAnd IBMother liquor.First, the table of 10mL deionized waters is measured
Face tension.Then untested compound (the compound I of designated volume is instilled successively with pipetteAAnd IB) mother liquor, after stirring evenly
The surface tension of solution is measured, three groups of experimental datas are recorded and is averaged.The surface tension to repeat the above steps to solution becomes
In stabilization.
According to the data that a series of surface tension measured change with concentration, calculating respectively obtains compound IAAnd IBTable
Face performance parameter.Including critical micelle concentration (CMC), the surface tension (γ of aqueous solution when CMCCMC), (π is pressed on surfaceCMC), absorption
Efficiency (C20), interface saturated extent of adsorption (τCMC) and gas-water interface saturation absorption when surfactant molecular area (Amin)。
Specifically it is shown in Table 1. (compound IAAnd IBSurface property parameter).
Second group of (compound IC-IG) the specific test method is as follows：
The compound I of a concentration of 1mmol/L has been respectively configuredC-IGAqueous solution, and determine the surface under the concentration
Power and to characterize its reduce aqueous solution surface tension ability.Specifically it is shown in Table 2. (compound IC-IGSurface property parameter).
Table 1.
Table 2.
CTAB is existing commercial cationic surfactant in table 1.：Cetyl trimethylammonium bromide is (as a contrast
Object).
By table 1 and 2 it is found that compound IA-IGIt can be used as cationic surfactant, and part of compounds (chemical combination
Object IAAnd IB) surface property be far superior to the surface property of CTAB.
Embodiment 9
Compound IA-IGThe test of antibacterial activity
Test strain is gram positive bacterial strain staphylococcus aureus (S.aureusATCC 25923) and glutamic acid rod
Shape bacillus (C.glutamicumATCC 13032).
The specific test method is as follows：
Absorption freezes 100 μ L of glycerol tube bacterium solution and is seeded in the shaking flask containing 50mL brain heart oxoid meat soups.At 30 DEG C,
Overnight incubation under conditions of 220rpm.By untested compound (compound IA-IG) first use 1mL methanol dissolve, then diffuse to 9mL without
In bacterium water, configuration obtains the untested compound mother liquor of a concentration of 1280 μ g/mL.It prepares without compound and only contains simultaneously
The solvent control group of 1mL methanol and 9mL sterile waters contains only the blank control group of 10mL sterile waters, and with commercial antimicrobial agent：16
Alkyl trimethyl ammonium chloride (BenzalkoniumChloride is abbreviated as " BAC ") is used as positive controls.
1mL untested compound mother liquors are drawn, 0.22 μm of organic phase filter membrane is crossed, is collected in 2mL small test tubes, and are used twice
Diluted method obtain 11 concentration compound test fluid (concentration is followed successively by 1280 μ g/mL, 640 μ g/mL, 320 μ g/mL,
160 μ g/mL, 80 μ g/mL, 40 μ g/mL, 20 μ g/mL, 10 μ g/mL, 5 μ g/mL, 2.5 μ g/mL and 1.25 μ g/mL).Not by 11
Compound test fluid with concentration respectively takes 10 μ L and is added in the designation hole of 96 orifice plates.The bacterium solution being incubated overnight is taken out simultaneously,
And therefrom draw in 2mL to 200mL fluid nutrient mediums, after rocking uniformly, 90 μ L bacterium solutions are drawn in 96 orifice plates.To be measuredization at this time
Close object a concentration of 128 μ g/mL, 64 μ g/mL, 32 μ g/mL, 16 μ g/mL, 8 μ g/mL, 4 μ g/mL, 2 μ g/mL, 1 μ g/mL, 0.5 μ g/
ML, 0.25 μ g/mL and 0.125 μ g/mL.
It is positioned over bacterium solution is added in shaking table with the microwell plate for testing compound solution, with 220rpm under preference temperature
Rotating speed culture 24 hours.Bacterial growth situation is estimated after culture, and (muddiness indicates that bacterial growth is all right, and clarification indicates
Bacterial growth situation is suppressed).Can inhibit the minimum compound concentration of bacterial growth as minimum inhibitory concentration in micropore
(Minimal Inhibitory Concentration, be abbreviated as " MIC ").The experimental results showed that solvent methanol can not inhibit
Bacterial growth, therefore do not generate interference to antibacterial test.
Compound IA-IGMIC value be shown in Table 3..
Table 3.
By table 3. it is found that compound IA-IGMiddle overwhelming majority compound has antibacterial activity, part to gram-positive bacteria
Compound (compound IEAnd IF) anti-microbial property close to commercial antimicrobial agent (BAC) anti-microbial property.
Claims (5)
1. a kind of quaternary amine of group containing anacardol is compound shown in Formulas I：
In Formulas I, R1Linear or branched alkyl group or halogenated carbon atom for carbon atom more than or equal to four are greater than or equal to four
Linear or branched alkyl group；R2For C15Chain alkyl；X is halogen.
2. quaternary amine as described in claim 1, which is characterized in that wherein R1For C4~C14Linear or branched alkyl group or halogenated
C4~C14Linear or branched alkyl group.
3. quaternary amine as claimed in claim 2, which is characterized in that wherein R1For C4~C14Straight chained alkyl.
4. quaternary amine as described in claim 1, which is characterized in that wherein R2For C15Straight chained alkyl.
5. quaternary amine as claimed in claims 3 and 4 is answered as the cationic surfactant with resisting gram-positive bacteria
With.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110105284A (en) * | 2019-05-30 | 2019-08-09 | 上海邦高化学有限公司 | Cashew nut phenol quaternary ammonium salt and application thereof |
| CN111690476A (en) * | 2020-06-22 | 2020-09-22 | 王智勇 | Special cleaning agent for garbage can and preparation method thereof |
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| CN110105284B (en) * | 2019-05-30 | 2022-07-12 | 上海邦高化学有限公司 | Quaternary ammonium salt of cardanol and application thereof |
| CN111690476A (en) * | 2020-06-22 | 2020-09-22 | 王智勇 | Special cleaning agent for garbage can and preparation method thereof |
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