CN113666903B - Preparation method of sesamol - Google Patents
Preparation method of sesamol Download PDFInfo
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- CN113666903B CN113666903B CN202111022826.4A CN202111022826A CN113666903B CN 113666903 B CN113666903 B CN 113666903B CN 202111022826 A CN202111022826 A CN 202111022826A CN 113666903 B CN113666903 B CN 113666903B
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- diphenol
- sesamol
- chloro
- triphenol
- sodium hydroxide
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- LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Natural products OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 title claims abstract description 39
- UIOFUWFRIANQPC-JKIFEVAISA-N Floxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl UIOFUWFRIANQPC-JKIFEVAISA-N 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 14
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims abstract description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000007864 aqueous solution Substances 0.000 claims abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 238000001953 recrystallisation Methods 0.000 claims description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- -1 sodium hydroxide-methylene dichloride-toluene Chemical compound 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 239000002024 ethyl acetate extract Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 238000003786 synthesis reaction Methods 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 239000008159 sesame oil Substances 0.000 description 6
- 235000011803 sesame oil Nutrition 0.000 description 6
- 239000013078 crystal Substances 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
- 241000207961 Sesamum Species 0.000 description 2
- 235000003434 Sesamum indicum Nutrition 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 229930013686 lignan Natural products 0.000 description 2
- 235000009408 lignans Nutrition 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241000764238 Isis Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 150000005692 lignans Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000004112 neuroprotection Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000011020 pilot scale process Methods 0.000 description 1
- MXXWOMGUGJBKIW-YPCIICBESA-N piperine Chemical compound C=1C=C2OCOC2=CC=1/C=C/C=C/C(=O)N1CCCCC1 MXXWOMGUGJBKIW-YPCIICBESA-N 0.000 description 1
- 229940075559 piperine Drugs 0.000 description 1
- WVWHRXVVAYXKDE-UHFFFAOYSA-N piperine Natural products O=C(C=CC=Cc1ccc2OCOc2c1)C3CCCCN3 WVWHRXVVAYXKDE-UHFFFAOYSA-N 0.000 description 1
- 235000019100 piperine Nutrition 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/64—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention belongs to the technical field of compound synthesis, and particularly relates to a preparation method of sesamol, which comprises the steps of preparing 2-chloro-1, 4-diphenol from p-diphenol and chlorine gas, then reacting the 2-chloro-1, 4-diphenol with sodium hydroxide aqueous solution to obtain 1,2, 4-triphenol, and finally reacting the 1,2, 4-triphenol with dichloromethane to obtain sesamol. The invention provides a new way for preparing sesamol, and the yield of sesamol is obviously improved.
Description
Technical Field
The invention belongs to the technical field of compound synthesis, and particularly relates to a preparation method of sesamol.
Background
Sesamol has chemical name of 3, 4-methylenedioxyphenol and molecular formula of C 7 H 6 O 3 The structural formula isIs a natural fat-soluble lignan compound in sesame oil (Chen Jinying, luo Zhongming. Research on sesamol stability [ J)]Food research and development 2015, 36 (4): 14-18; ren Xiaona and Zeng Jun the current state of research on lignans in sesame [ J]Food industry technology, 2014, 35 (1): 383-386).
Sesamol is a main component of sesame oil, and also a component that imparts a special flavor to sesame oil. Sesamol can make sesame oil more stable in quality, and also has the effects of resisting bacteria, inflammation, oxidation, melanin, aging, cancer, neuroprotection, losing weight and the like (Ma Congcong, xu Jiqu, zhao Saiqi, yang Bei, yang Chen, huang Qingde. Sesamol biological activity research progress [ J ]. Chinese food and nutrition, 2019, 25 (9): 62-65; ma Congcong, xu Jiqu, zhao Saiqi, yang Bei, huang Qingde. Sesamol anti-inflammatory mechanism research progress [ J ]. Chinese grease, 2019, 44 (9): 109-113).
At present, sesamol is obtained by two ways, one is obtained by extraction and separation from sesame oil, and the other is obtained by synthesis. However, sesamol is extracted from sesame oil, which is costly and costly due to the high solvent consumption.
The manual synthesis method of sesamol mainly comprises two steps: the total synthesis and the semisynthesis (https:// www.yixue.com/%E8A%9D%E9%BA%BB%E9%85%9A, medical encyclopedia, sesamol) are carried out by taking piperine as a raw material. However, the two methods are adopted to synthesize sesamol, and the yield is low, about 60%.
Disclosure of Invention
Accordingly, an object of the present invention is to provide a process for producing sesamol with a high yield.
In order to achieve the above purpose, the technical scheme of the invention is as follows:
the preparation method of sesamol is characterized in that 2-chloro-1, 4-diphenol is prepared by taking p-diphenol and chlorine gas as raw materials.
Further, the preparation of the 2-chloro-1, 4-diphenol specifically comprises: heating p-diphenol and reduced iron powder to boiling in the presence of carbon tetrachloride, and introducing chlorine under the irradiation of an ultraviolet light source; after the chlorine is introduced, continuing to reflux for 1-10h, and introducing nitrogen after the reaction is completed; filtering while hot, cooling, standing, filtering and recrystallizing the obtained filter residue.
Further, the chlorine is used in a molar ratio of 2:1-5:1 with respect to the para-diphenol.
Further, recrystallization during the preparation of 2-chloro-1, 4-biphenol means recrystallization with acetone.
Further, the preparation of the 1,2, 4-trisphenol specifically comprises: heating 2-chloro-1, 4-diphenol and sodium hydroxide water solution to 40-100 ℃ and reacting at the temperature for 1-16h; after the reaction was completed, cooling, extraction with ethyl acetate and distillation of the ethyl acetate extract under reduced pressure was performed, followed by recrystallization.
Further, the molar ratio of the 2-chloro-1, 4-diphenol to the sodium hydroxide is 1:1-1:3.
Further, the recrystallization during the preparation of 1,2, 4-trisphenol means recrystallization from diethyl ether.
Further, the reaction of 1,2, 4-trisphenol and methylene dichloride to prepare sesamol is specifically as follows: heating sodium hydroxide-methylene dichloride-toluene to 80-100 ℃, adding a 1,2, 4-triphenol-toluene mixture, then reacting for 0.5-3h at 100-110 ℃, cooling, filtering and recrystallizing the obtained filter residue.
Further, the molar ratio of the dichlorotoluene to the 1,2, 4-triphenol is 1:1-1:2.
Further, the recrystallization in the process of preparing sesamol by reacting 1,2, 4-triphenol with sodium hydroxide means recrystallization by using petroleum ether with a boiling range of 60-90 ℃.
The invention has the beneficial effects that:
the invention obviously improves the yield of sesamol.
The invention provides a new synthesis path of sesamol.
The invention has low cost of raw materials and simple process, and is beneficial to realizing pilot-scale production or industrial production.
Drawings
FIG. 1 is a diagram showing a process route for preparing sesamol according to the present invention;
FIG. 2 shows sesamol obtained in example 1 1 H nuclear magnetic resonance plot, the abscissa is chemical shift;
FIG. 3 shows sesamol obtained in example 1 13 C nuclear magnetic resonance diagram, the abscissa is chemical shift.
Detailed Description
The examples are presented for better illustration of the present invention, but are not intended to limit the scope of the present invention to the examples. Those skilled in the art will appreciate that various modifications and adaptations of the embodiments described above are possible in light of the above teachings and are intended to be within the scope of the invention.
Example 1
The preparation method of sesamol comprises the following specific steps:
(1) Synthesis of 2-chloro-1, 4-diphenol
11.01g (0.10 mol) of p-diphenol and 2.80g (0.05 mol) of reduced iron powder are weighed into a 500mL round bottom flask, 150mL of carbon tetrachloride is added into the round bottom flask, and the mixture is fully dissolved by magnetic stirring; heating to boiling, and slowly introducing 0.40mL of chlorine at a constant speed under the irradiation of an ultraviolet light source; after the chlorine is introduced, continuing to magnetically stir and reflux the mixture for 5 hours, and introducing nitrogen after the reaction is completed; filtering while the mixture is hot, cooling, standing, precipitating white crystals, filtering (recovering carbon tetrachloride in filtrate), collecting filter residues, and recrystallizing the filter residues with acetone to obtain 13.54g of white crystal 2-chloro-1, 4-diphenol, namely, the yield of 2-chloro-1, 4-diphenol is 93.6%.
(2) Synthesis of 1,2, 4-trisphenol
14.46g (0.10 mol) of 2-chloro-1, 4-diphenol and 6.0g of sodium hydroxide solid (0.15 mol) are weighed into a 500mL round bottom flask and 150mL distilled water is added to the flask and stirred magnetically to make it well miscible; heating to 80 ℃, and magnetically stirring at constant temperature for reaction for 8 hours; after completion of the reaction, cooling, extraction with ethyl acetate, collection of the organic layer, and distillation of the ethyl acetate extract under reduced pressure gave a crude product, which was recrystallized from diethyl ether to give 11.90g of 1,2, 4-trisphenol as a leaf-like crystal, in which step the yield of 1,2, 4-trisphenol was 94.4%.
(3) Synthesis of sesamol
12.61g (0.10 mol) of 1,2, 4-trisphenol was weighed out and dissolved in 30mL of toluene to obtain a 1,2, 4-trisphenol-toluene solution;
8.0g of sodium hydroxide solid (0.2 mol) and 8.09mL (0.12 mol) of methylene chloride are placed in a 500mL round-bottom flask, 100mL of toluene is added into the round-bottom flask, heating and magnetic stirring are carried out, and when the temperature is increased to 90 ℃,1,2, 4-triphenol-toluene solution is slowly added dropwise; controlling the dropping speed and the reaction temperature of the 1,2, 4-triphenol-toluene solution, dropping at the speed of 12 drops/min, and controlling the reaction temperature at 95 ℃; after the dripping is finished, stirring and reacting for 1h at the constant temperature of 105 ℃; after the reaction is completed, cooling, filtering, collecting filter residues and recovering toluene; the residue was recrystallized from 60-90℃petroleum ether to give 12.72g of sesamol as white needle crystals, and the yield of sesamol in this step was 92.1%.
That is, in this example, the total yield of sesamol is 93.6% by 94.4% by 92.1% by 81.38%.
Performance detection
Nuclear magnetic resonance was performed on sesamol obtained in example 1 1 H detection and nuclear magnetic resonance 13 C, detecting, wherein the result is shown in the figures 1-2;
wherein, nuclear magnetic resonance 1 H and nuclear magnetic resonance 13 The detection method is as follows; in D 2 O is solvent, and a polysaccharide solution of 50mg/mL is prepared. 1 H NMR 13 The C NMR spectrum was recorded using Bruker AV III-600NMR spectrum.
As can be seen from FIG. 1, sesame seedsNuclear magnetic resonance hydrogen spectrum data of phenol 1 H NMR(600MHz,DMSO-d 6 )δ:5.90(2H,s,-CH 2 -),6.20(1H,dd,J＝8.4,2.5Hz,Ph-H),6.39(1H,d,J＝2.4Hz,Ph-H),6.70(1H,d,J＝8.3Hz,Ph-H),9.12(1H,s,-OH)。
As can be seen from FIG. 2, the nuclear magnetic resonance carbon spectrum data of sesamol 13 C NMR(100MHz,DMSO-d 6 )δ:98.3,101.0,106.7,108.6,140.1,148.2,153.0。
Furthermore, it should be understood that although the present disclosure describes embodiments, not every embodiment is provided with a separate embodiment, and that this description is provided for clarity only, and that the disclosure is not limited to the embodiments described in detail below, and that the embodiments described in the examples may be combined as appropriate to form other embodiments that will be apparent to those skilled in the art.
Claims (6)
1. A process for producing sesamol, which comprises the steps of,
s1, firstly, preparing 2-chloro-1, 4-diphenol by taking p-diphenol and chlorine gas as raw materials, wherein the preparation of the 2-chloro-1, 4-diphenol specifically comprises the following steps: heating p-diphenol and reduced iron powder to boiling in the presence of carbon tetrachloride, and introducing chlorine under the irradiation of an ultraviolet light source; after the chlorine is introduced, continuing to reflux for 1-10h, and introducing nitrogen after the reaction is completed; filtering while hot, cooling, standing, filtering, and recrystallizing the obtained filter residue;
s2, subsequently reacting 2-chloro-1, 4-diphenol with sodium hydroxide aqueous solution to obtain 1,2, 4-triphenol, wherein the preparation of the 1,2, 4-triphenol comprises the following specific operations: heating 2-chloro-1, 4-diphenol and sodium hydroxide water solution to 40-100 ℃ and reacting at the temperature for 1-16h; after the reaction was completed, cooling, extraction with ethyl acetate, and distillation of the ethyl acetate extract under reduced pressure followed by recrystallization;
s3, finally reacting 1,2, 4-triphenol with dichloromethane to prepare sesamol, wherein the preparation of sesamol specifically comprises the following steps: heating sodium hydroxide-methylene dichloride-toluene to 80-100 ℃, adding a 1,2, 4-triphenol-toluene mixture, then reacting for 0.5-3h at 100-110 ℃, cooling, filtering and recrystallizing the obtained filter residue.
2. The method according to claim 1, wherein in step S1, the recrystallization means recrystallization with acetone.
3. The method of claim 1, wherein in step S1, the molar ratio of chlorine to p-diphenol is from 2:1 to 5:1.
4. The process according to claim 1, wherein in step S2, the molar ratio of 2-chloro-1, 4-diphenol to sodium hydroxide is from 1:1 to 1:3.
5. The process according to claim 1, wherein in step S3, the molar ratio of dichloromethane to 1,2, 4-trisphenol is from 1:1 to 1:2.
6. The method according to claim 1, wherein in step S3, the recrystallization is performed by petroleum ether.
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| US4609669A (en) * | 1984-09-11 | 1986-09-02 | Nihon Tokushu Noyaku Seizo K.K. | Carbamoylimidazole derivatives and fungicidal use thereof |
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| US4609669A (en) * | 1984-09-11 | 1986-09-02 | Nihon Tokushu Noyaku Seizo K.K. | Carbamoylimidazole derivatives and fungicidal use thereof |
| CN1282730A (en) * | 2000-07-19 | 2001-02-07 | 杨振华 | Compounds with particular structure and anticancer activity and its preparing process |
| CN106565421A (en) * | 2016-11-08 | 2017-04-19 | 岳阳中科华昂精细化工科技有限公司 | Preparation method of 2,3,5,6-tetrafluorohydrazine-1,4-benzene dimethanol |
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| Title |
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