CN113636997A - Diphenyl ether new compound containing 4-hydroxy-2H-1-benzopyran-2-one fragment and preparation method thereof - Google Patents
Diphenyl ether new compound containing 4-hydroxy-2H-1-benzopyran-2-one fragment and preparation method thereof Download PDFInfo
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- CN113636997A CN113636997A CN202111041171.5A CN202111041171A CN113636997A CN 113636997 A CN113636997 A CN 113636997A CN 202111041171 A CN202111041171 A CN 202111041171A CN 113636997 A CN113636997 A CN 113636997A
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- Prior art keywords
- hydroxy
- benzopyran
- diphenyl ether
- phenoxy
- compound containing
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- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 150000001875 compounds Chemical class 0.000 title claims abstract description 16
- VXIXUWQIVKSKSA-UHFFFAOYSA-N 4-hydroxycoumarin Chemical group C1=CC=CC2=C1OC(=O)C=C2O VXIXUWQIVKSKSA-UHFFFAOYSA-N 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title abstract description 5
- -1 nitro, methyl Chemical group 0.000 claims abstract description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 239000000460 chlorine Chemical group 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 125000002560 nitrile group Chemical group 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 238000010992 reflux Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical group CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 7
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 239000002798 polar solvent Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 238000000967 suction filtration Methods 0.000 claims description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 239000012279 sodium borohydride Substances 0.000 claims description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 238000007865 diluting Methods 0.000 claims description 3
- 238000010790 dilution Methods 0.000 claims description 3
- 239000012895 dilution Substances 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 238000004321 preservation Methods 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- BDTJIVUVQRVLLJ-UHFFFAOYSA-N 1-[2-chloro-4-(4-chlorophenoxy)phenyl]ethanone Chemical compound C1=C(Cl)C(C(=O)C)=CC=C1OC1=CC=C(Cl)C=C1 BDTJIVUVQRVLLJ-UHFFFAOYSA-N 0.000 description 1
- 239000005966 Bromadiolone Substances 0.000 description 1
- OWNRRUFOJXFKCU-UHFFFAOYSA-N Bromadiolone Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1C(O)CC(C=1C(OC2=CC=CC=C2C=1O)=O)C1=CC=CC=C1 OWNRRUFOJXFKCU-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000003128 rodenticide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
- C07D311/56—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 without hydrogen atoms in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a diphenyl ether new compound containing 4-hydroxy-2H-1-benzopyran-2-ketone segments and a preparation method thereof, wherein the structural formula of the diphenyl ether new compound containing 4-hydroxy-2H-1-benzopyran-2-ketone segments is as follows:
Description
Technical Field
The invention relates to a diphenyl ether new compound containing 4-hydroxy-2H-1-benzopyran-2-ketone segment and a preparation method thereof.
Background
The molecular structures of rodenticide bromadiolone and bromratin both contain 4-hydroxy-2H-1-benzopyran-2-one fragments and have similar structures, so that some compounds of diphenyl ethers with similar structures containing 4-hydroxy-2H-1-benzopyran-2-one fragments are synthesized, and novel compounds possibly having practical values are searched.
Disclosure of Invention
The invention aims to provide a novel diphenyl ether compound containing 4-hydroxy-2H-1-benzopyran-2-one fragments and a preparation method thereof, wherein the reaction steps are few, and the conditions are mild.
The technical solution of the invention is as follows:
a diphenyl ether new compound containing 4-hydroxy-2H-1-benzopyran-2-one fragment is characterized in that:
the structural formula of the diphenyl ether new compound containing 4-hydroxy-2H-1-benzopyran-2-one fragments is as follows:
wherein X, Y is hydrogen, chlorine, bromine, nitro, methyl or nitrile group.
The diphenyl ether new compound containing 4-hydroxy-2H-1-benzopyran-2-ketone segment is 3- [3- (2-chloro-4-p-chlorophenoxy-phenyl) -3-carbonyl-1-phenylpropyl ] -4-hydroxycoumarin.
A synthetic method of the diphenyl ether new compound containing 4-hydroxy-2H-1-benzopyran-2-ketone segment is characterized in that: comprises the following steps:
step (1): adding alkali into water or an alcohol polar solvent, stirring for dissolving, then adding 2-X-4- (4-Y-phenoxy) acetophenone, dropwise adding benzaldehyde at the temperature of-15-45 ℃, stirring for 0.1-10 h after dropwise adding, adding water for diluting, and dewatering to obtain 2-X-4- (4-Y-phenoxy) phenylpropenone;
step (2): adding 2-X-4- (4-Y-phenoxy) phenyl phenylpropenones and 4-hydroxycoumarin into a polar solvent, adding a catalyst organic base, heating to reflux, carrying out reflux and heat preservation for 5-20 hours, distilling out most of the solvent under normal pressure, adding methanol, stirring and cooling to room temperature, and precipitating 3- [3- (2-X-4-p-Y-phenoxy-phenyl) -3-carbonyl-1-phenylpropyl ] -4-hydroxycoumarin;
and (3): adding 3- [3- (2-X-4-p-Y-phenoxy-phenyl) -3-carbonyl-1-phenylpropyl ] -4-hydroxycoumarin into an alcohol solvent, controlling the temperature to be 0-35 ℃, adding potassium borohydride or sodium borohydride in batches, heating, refluxing, preserving heat, cooling, performing suction filtration, distilling most of the solvent out of the filtrate, adding water for dilution, and separating out the 3- [3- (2-X-4-p-Y-phenoxy-phenyl) -3-hydroxy-1-phenylpropyl ] -4-hydroxycoumarin which is a white-like solid.
The catalyst organic base is N-methylmorpholine, hexahydropiperidine, trimethylamine or triethylamine.
The alcohol polar solvent in the step (1) can be methanol, ethanol, propanol, isopropanol, n-butanol, isobutanol or a mixture of the above substances; the dripping temperature is-25 to 55 ℃, and the preferable temperature is-10 to 15 ℃.
The alkali in the step (1) can be sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methoxide, triethylamine and pyridine.
The polar solvent in the step (2) can be acetone, acetonitrile, dioxane and glycol dimethyl ether, and the reflux temperature is changed according to the change of the selected solvent.
The solvent in step (3) may be methanol, ethanol, propanol, isopropanol, n-butanol, isobutanol, or a mixture thereof.
The molar ratio of the reducing agent potassium borohydride or sodium borohydride to the 3- [3- (2-chloro-4-p-chlorophenoxy-phenyl) -3-carbonyl-1-phenylpropyl ] -4-hydroxycoumarin in the step (3) is 0.25: 1-1: 1.
the invention has the following positive effects: the diphenyl ether new compound containing 4-hydroxy-2H-1-benzopyran-2-one segment is synthesized, the reaction steps are few, the condition is mild, and the method has potential special application, so the method has important practical value.
The present invention will be further described with reference to the following examples.
Detailed Description
Example 1:
3- [3- (2-chloro-4-p-chlorophenoxy-phenyl) -3-hydroxy-1-phenylpropyl ] -4-hydroxycoumarin synthesis:
(1) adding 12 g of sodium hydroxide into 45 g of water, stirring for dissolving, adding 100 g of 95% ethanol, then adding 16 g of 2-chloro-4- (4-chlorophenoxy) acetophenone, dripping 10.5 g of benzaldehyde at the temperature of 5-10 ℃, stirring for 4h after dripping, adding 200 ml of water for diluting, standing, and dewatering to obtain 25 g of yellow viscous oily matter which is 2-chloro-4- (4-chlorophenoxy) phenylpropenon (solidified after standing).
(2) Adding 20 g of 2-chloro-4- (4-chlorophenoxy) phenylpropenones and 7 g of 4-hydroxycoumarin into 120 ml of dioxane, adding 1.2 g of N-methylmorpholine, heating to reflux, carrying out reflux and heat preservation for 5 hours, distilling out most of solvent under normal pressure, adding a proper amount of methanol, stirring and cooling to room temperature, separating out solid, and carrying out suction filtration to obtain 24.2 g of white solid which is 3- [3- (2-chloro-4-p-chlorophenoxy-phenyl) -3-carbonyl-1-phenylpropyl ] -4-hydroxycoumarin.
(3) Adding 5 g of 3- [3- (2-chloro-4-p-chlorophenoxyl-phenyl) -3-carbonyl-1-phenylpropyl ] -4-hydroxycoumarin into 120 ml of ethanol, controlling the temperature to be 30-35 ℃, adding 1.6 g of sodium borohydride in batches, heating, refluxing and preserving the temperature for 4 hours after the addition, cooling, performing suction filtration, distilling most of solvent out of filtrate, adding water for dilution, separating out solid, performing suction filtration and drying to obtain 4.3 g of white solid with the content of 96 percent, wherein the content of the white solid is 3- [3- (2-chloro-4-p-chlorophenoxyl-phenyl) -3-hydroxy-1-phenylpropyl ] -4-hydroxycoumarin.
Claims (4)
1. A diphenyl ether new compound containing 4-hydroxy-2H-1-benzopyran-2-one fragment is characterized in that:
the structural formula of the diphenyl ether new compound containing 4-hydroxy-2H-1-benzopyran-2-one fragments is as follows:
wherein X, Y is hydrogen, chlorine, bromine, nitro, methyl or nitrile group.
2. The novel diphenyl ether compounds containing 4-hydroxy-2H-1-benzopyran-2-one segment as claimed in claim 1, wherein: the diphenyl ether new compound containing 4-hydroxy-2H-1-benzopyran-2-ketone segment is 3- [3- (2-chloro-4-p-chlorophenoxy-phenyl) -3-carbonyl-1-phenylpropyl ] -4-hydroxycoumarin.
3. A method for synthesizing the diphenyl ether compounds containing 4-hydroxy-2H-1-benzopyran-2-one fragment according to claim 1, which comprises the following steps: comprises the following steps:
the first step is as follows: adding alkali into water or an alcohol polar solvent, stirring for dissolving, then adding 2-X-4- (4-Y-phenoxy) acetophenone, dropwise adding benzaldehyde at the temperature of-15-45 ℃, stirring for 0.1-10 h after dropwise adding, adding water for diluting, and dewatering to obtain 2-X-4- (4-Y-phenoxy) phenylpropenone;
the second step is that: adding 2-X-4- (4-Y-phenoxy) phenyl phenylpropenones and 4-hydroxycoumarin into a polar solvent, adding a catalyst organic base, heating to reflux, carrying out reflux and heat preservation for 5-20 hours, distilling out most of the solvent under normal pressure, adding methanol, stirring and cooling to room temperature, and precipitating 3- [3- (2-X-4-p-Y-phenoxy-phenyl) -3-carbonyl-1-phenylpropyl ] -4-hydroxycoumarin;
the third step: adding 3- [3- (2-X-4-p-Y-phenoxy-phenyl) -3-carbonyl-1-phenylpropyl ] -4-hydroxycoumarin into an alcohol solvent, controlling the temperature to be 0-35 ℃, adding potassium borohydride or sodium borohydride in batches, heating, refluxing, preserving heat, cooling, performing suction filtration, distilling most of the solvent out of the filtrate, adding water for dilution, and separating out the 3- [3- (2-X-4-p-Y-phenoxy-phenyl) -3-hydroxy-1-phenylpropyl ] -4-hydroxycoumarin which is a white-like solid.
4. The method for synthesizing the diphenyl ether compounds containing 4-hydroxy-2H-1-benzopyran-2-one segment as claimed in claim 3, wherein the method comprises the following steps: the catalyst organic base is N-methylmorpholine, hexahydropiperidine, trimethylamine or triethylamine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111041171.5A CN113636997A (en) | 2021-09-07 | 2021-09-07 | Diphenyl ether new compound containing 4-hydroxy-2H-1-benzopyran-2-one fragment and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111041171.5A CN113636997A (en) | 2021-09-07 | 2021-09-07 | Diphenyl ether new compound containing 4-hydroxy-2H-1-benzopyran-2-one fragment and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN113636997A true CN113636997A (en) | 2021-11-12 |
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| CN202111041171.5A Pending CN113636997A (en) | 2021-09-07 | 2021-09-07 | Diphenyl ether new compound containing 4-hydroxy-2H-1-benzopyran-2-one fragment and preparation method thereof |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110845462A (en) * | 2019-12-09 | 2020-02-28 | 沈阳爱威科技发展股份有限公司 | Industrial production method for controlling isomer ratio of bromadiolone liquid parent drug |
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2021
- 2021-09-07 CN CN202111041171.5A patent/CN113636997A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110845462A (en) * | 2019-12-09 | 2020-02-28 | 沈阳爱威科技发展股份有限公司 | Industrial production method for controlling isomer ratio of bromadiolone liquid parent drug |
Non-Patent Citations (2)
| Title |
|---|
| ILIA MANOLOV ET AL.: "Synthesis and Pharmacological Investigations of Some 4-Hydroxycoumarin Derivatives", ARCH. PHARM. PHARM. MED. CHEM., vol. 2, pages 83 - 94 * |
| MEIJING WANG ET AL.: "Synthesis and Insecticidal Activity of New 4-Hydroxy-2H-1-benzopyran-2-one Derivatives", APPL BIOCHEM BIOTECHNOL, vol. 159, pages 768 - 777 * |
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