CN116730811A - Preparation method of synthetic chiral camphor type beta-diketone - Google Patents
Preparation method of synthetic chiral camphor type beta-diketone Download PDFInfo
- Publication number
- CN116730811A CN116730811A CN202310556398.6A CN202310556398A CN116730811A CN 116730811 A CN116730811 A CN 116730811A CN 202310556398 A CN202310556398 A CN 202310556398A CN 116730811 A CN116730811 A CN 116730811A
- Authority
- CN
- China
- Prior art keywords
- camphor
- diketone
- type beta
- trifluoroacetyl
- chiral
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229960000846 camphor Drugs 0.000 title claims abstract description 31
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 title claims abstract description 28
- 241000723346 Cinnamomum camphora Species 0.000 title claims abstract description 25
- 229930008380 camphor Natural products 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 54
- 238000003756 stirring Methods 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 239000012043 crude product Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 6
- STSCVKRWJPWALQ-UHFFFAOYSA-N TRIFLUOROACETIC ACID ETHYL ESTER Chemical compound CCOC(=O)C(F)(F)F STSCVKRWJPWALQ-UHFFFAOYSA-N 0.000 claims description 6
- 239000008367 deionised water Substances 0.000 claims description 6
- 229910021641 deionized water Inorganic materials 0.000 claims description 6
- 239000005457 ice water Substances 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000012266 salt solution Substances 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 238000010025 steaming Methods 0.000 claims description 2
- ISLOIHOAZDSEAJ-UHFFFAOYSA-N 4,7,7-trimethyl-2-(2,2,2-trifluoroacetyl)bicyclo[2.2.1]heptan-3-one Chemical compound C1CC2(C)C(=O)C(C(=O)C(F)(F)F)C1C2(C)C ISLOIHOAZDSEAJ-UHFFFAOYSA-N 0.000 abstract description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 12
- 230000002194 synthesizing effect Effects 0.000 abstract description 7
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 238000006482 condensation reaction Methods 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229940025250 camphora Drugs 0.000 description 3
- 239000010238 camphora Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000003512 Claisen condensation reaction Methods 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000005622 photoelectricity Effects 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 230000009295 sperm incapacitation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method for synthesizing chiral camphor type beta-diketone, which comprises the following specific processes: step 1, preparing chiral camphor type beta-diketone-3-trifluoroacetyl camphor; and 2, purifying the product according to the product obtained in the step 1. The invention generates D/L-3-trifluoroacetyl camphor through direct condensation reaction of chiral camphor and ethyl acetate. The method for synthesizing chiral 3-trifluoroacetyl camphor has the advantages of simple process, single solvent type, higher yield and good application prospect in the aspects of chemical synthesis, photoelectric devices and the like.
Description
Technical Field
The invention belongs to the technical field of nanometer high polymer materials, and relates to a preparation method for synthesizing chiral camphor type beta-diketone.
Background
Beta-dicarbonyl compounds have a critical role in synthetic organic chemistry as intermediates in chemical synthesis. Camphortype beta-diketones are produced from camphora and esters having carbonyl groups by aldol condensation, but the camphora type beta-diketones are difficult to synthesize because of the unique spatial structure of camphora, which makes the carbon at the alpha position thereof difficult to activate. At present, most of the research on camphor type beta-diketones has complex reaction process and reduces the synthesis efficiency.
Disclosure of Invention
The invention aims to provide a preparation method for synthesizing chiral camphor type beta-diketone, which enables chiral camphor to be directly condensed with ethyl acetate, simplifies the reaction process and improves the synthesis efficiency.
The technical scheme adopted by the invention is that the preparation method for synthesizing chiral camphor type beta-diketone specifically comprises the following steps:
step 1, preparing chiral camphor type beta-diketone-3-trifluoroacetyl camphor;
and 2, purifying the product obtained in the step 2.
The invention is also characterized in that:
the specific process of the step 1 is as follows:
D/L-camphor and tetrahydrofuran in N 2 Adding the mixture into a double-neck flask under the environment, dropwise adding ethyl trifluoroacetate in the ice bath under stirring, stirring and refluxing, and continuing stirring at room temperature for reaction overnight to obtain a crude product D/L-3-trifluoroacetyl camphor.
In the step 1, the stirring time of the ice bath is 30-60 min, and the reflux time is 3-6 h.
The specific process of the step 2 is as follows:
pouring the product obtained in the step 1 into a beaker filled with ice water, dropwise adding hydrochloric acid to adjust Ph value to be acidic, pouring into a separating funnel, extracting with diethyl ether, and combining diethyl ether layers; then, the diethyl ether layer is sequentially washed in sodium bicarbonate solution and saturated salt solution, then washed in deionized water, finally dried by adding anhydrous magnesium sulfate, the solvent is distilled off in a rotary way, and separation and purification are carried out by using a silica gel chromatographic column to obtain orange liquid, namely D/L-3-trifluoroacetyl camphor D/L-TFC.
In the step 2, the rotary steaming temperature is 30-35 ℃.
The invention has the beneficial effects that the D/L-3-trifluoroacetyl camphor is generated through the claisen condensation reaction between the chiral camphor and the ethyl acetate. The method for synthesizing chiral 3-trifluoroacetyl camphor has the advantages of simple process, single solvent type, higher yield and good application prospect in the aspects of chemical synthesis, photoelectric devices and the like.
Drawings
FIG. 1 is a hydrogen spectrum of 3-trifluoroacetyl camphor (D/L-TFC) in deuterated chloroform solvent according to example 1 of the preparation method of the synthetic chiral camphor type beta-diketone of the present invention;
FIG. 2 shows the preparation method of the synthetic chiral camphor type beta-diketone of the present invention in example 1, 3-trifluoroacetyl camphor (D/L-TFC) is dissolved in CCl 3 An ultraviolet absorption spectrum of (a);
FIG. 3 shows the preparation method of the synthetic chiral camphor type beta-diketone of the present invention in example 1 wherein chiral 3-trifluoroacetyl camphor (D/L-TFC) is dissolved in CCl 3 CD profile of (c).
Detailed Description
The invention will be described in detail below with reference to the drawings and the detailed description.
The invention discloses a preparation method for synthesizing chiral camphor type beta-diketone, which specifically comprises the following steps:
step 1, preparing a crude chiral camphor type beta-diketone-D/L-3-trifluoroacetyl camphor:
1.2-2 g D/L-camphor and 8-12 ml tetrahydrofuran are added in N 2 Into a 50ml double-neck flask, the mixture is stirred for 30min to 60min in an ice bath. Slowly dripping 1.2-2 ml of ethyl trifluoroacetate into the mixture under stirring, stirring and refluxing the mixture for 3-6 hours, and continuously stirring the mixture at room temperature for reaction overnight to obtain a crude product D/L-3-trifluoroacetyl camphor.
Step 2, purifying the product obtained in step 1:
the crude product was poured into a beaker containing 20-30 mL of ice water, 10% by mass of hydrochloric acid was added dropwise to adjust Ph to 2-3, the sample color was slowly faded to yellow, poured into a separating funnel, extracted with diethyl ether (3×20 mL), and the diethyl ether layers were combined. Subsequently, the diethyl ether layer is washed with saturated sodium bicarbonate solution with mass fraction of 5% for 1 time by washing with saturated salt and deionized water for 2 times, and finally dried by adding anhydrous magnesium sulfate. The solvent is distilled off by spin (the spin temperature is 30 ℃ to 35 ℃), and the orange liquid is obtained by further separation and purification by a silica gel chromatographic column, namely D/L-3-trifluoroacetyl camphor (D/L-TFC).
Example 1
1.2. 1.2g D/L-camphor and 8ml tetrahydrofuran are taken up in N 2 Into a 50ml two-necked flask, the mixture was added under the condition of ice bath stirring for 45min, 1.2ml of ethyl trifluoroacetate was slowly added dropwise during stirring, the mixture was stirred and refluxed for 4h, and the reaction was continued at room temperature under stirring overnight to obtain a crude product of 3-trifluoroacetyl camphor. The crude product was poured into a beaker containing 20mL of ice water, 10% by mass hydrochloric acid was added dropwise to adjust Ph to 2, the sample was slowly pale to yellow in color, poured into a separatory funnel, extracted with diethyl ether (3×20 mL), and the diethyl ether layers were combined. Subsequently, the diethyl ether layer is washed with saturated sodium bicarbonate solution with mass fraction of 5% for 1 time by washing with saturated salt and deionized water for 2 times, and finally dried by adding anhydrous magnesium sulfate. The solvent was distilled off by spin-evaporation at 32℃and further purified by column chromatography on silica gel to give an orange liquid, D/L-3-trifluoroacetyl camphor (D/L-TFC).
FIG. 1 is a hydrogen spectrum of the product 3-trifluoroacetyl camphor dissolved in deuterated chloroform solvent, 1 H NMR(600MHz，CDCl 3 delta/ppm): 2.86 (m, 1H), 2.06 (m, 1H), 1.73-1.83 (m, 2H), 1.41-1.53 (m, 2H), 1.02 (s, 3H), 0.97 (s, 3H), 0.86 (s, 3H); FIG. 2 shows the dissolution of the product 3-trifluoroacetyl camphor in CCl 3 The ultraviolet absorption spectrum of (2) showing a characteristic peak of beta-diketone, the high energy band in the 220-300nm range being due to pi-pi transition of 3-trifluoroacetyl camphor; FIG. 3 shows the dissolution of chiral 3-trifluoroacetyl camphor (D/L-TFC) in CCl 3 The two enantiomers showed almost identical absorbance spectra and a pair of perfect mirror-symmetrical CD signals, and a pair of sharp absorbance peaks at 333 nm.
Example 2
1.6. 1.6g D/L-camphor and 10ml tetrahydrofuran were added under N 2 Into a 50ml two-necked flask, the mixture was stirred in an ice bath for 60 minutes, 1.6ml of ethyl trifluoroacetate was slowly added dropwise thereto under stirring, the mixture was refluxed for 6 hours, and the reaction was continued under stirring at room temperatureThe crude product 3-trifluoroacetyl camphor was obtained overnight. The crude product was poured into a beaker containing 25mL of ice water, 10% by mass hydrochloric acid was added dropwise to adjust Ph to 2, the sample was slowly pale to yellow in color, poured into a separatory funnel, extracted with diethyl ether (3×20 mL), and the diethyl ether layers were combined. Subsequently, the diethyl ether layer is washed with saturated sodium bicarbonate solution with mass fraction of 5% for 1 time by washing with saturated salt and deionized water for 2 times, and finally dried by adding anhydrous magnesium sulfate. The solvent was distilled off by spin-evaporation at 30℃and further purified by silica gel column chromatography to give an orange liquid, namely D/L-3-trifluoroacetyl camphor (D/L-TFC).
Example 3
2g D/L-camphor and 12ml tetrahydrofuran are added under N 2 Into a 50ml two-necked flask, the mixture was stirred in an ice bath for 30min, 2ml of ethyl trifluoroacetate was slowly added dropwise thereto under stirring, the mixture was refluxed for 3h under stirring, and the reaction was continued at room temperature overnight under stirring to obtain a crude product of 3-trifluoroacetyl camphor. The crude product was poured into a beaker containing 30mL of ice water, 10% by mass hydrochloric acid was added dropwise to adjust Ph to 3, the sample was slowly pale to yellow in color, poured into a separatory funnel, extracted with diethyl ether (3×20 mL), and the diethyl ether layers were combined. Subsequently, the diethyl ether layer is washed with saturated sodium bicarbonate solution with mass fraction of 5% for 1 time by washing with saturated salt and deionized water for 2 times, and finally dried by adding anhydrous magnesium sulfate. The solvent was distilled off by spin-evaporation at 30℃and further purified by silica gel column chromatography to give an orange liquid, namely D/L-3-trifluoroacetyl camphor (D/L-TFC).
The invention mainly prepares chiral camphor type beta-diketone by a simple method, and the chiral camphor and ethyl acetate are directly condensed and reacted by a method of ice bath, oil bath and room temperature combination, so that the yield reaches 44 percent. Chiral as a natural product has great prospect in chemistry, materials and biology. The chiral reaction of substances, chiral synthesis and separation of substances and the like have important significance in incapacitation, and chiral complexes of the chiral complex are interesting to many researchers especially in the field of photoelectricity.
Claims (5)
1. The preparation method of the synthetic chiral camphor type beta-diketone is characterized by comprising the following steps: the method specifically comprises the following steps:
step 1, preparing chiral camphor type beta-diketone-3-trifluoroacetyl camphor;
and 2, purifying the product obtained in the step 2.
2. The method for preparing the synthetic chiral camphor type beta-diketone according to claim 1, which is characterized in that: the specific process of the step 1 is as follows:
D/L-camphor and tetrahydrofuran in N 2 Adding the mixture into a double-neck flask under the environment, dropwise adding ethyl trifluoroacetate in the ice bath under stirring, stirring and refluxing, and continuing stirring at room temperature for reaction overnight to obtain a crude product D/L-3-trifluoroacetyl camphor.
3. The method for preparing the synthetic chiral camphor type beta-diketone according to claim 2, which is characterized in that: in the step 1, the stirring time of the ice bath is 30-60 min, and the reflux time is 3-6 h.
4. The method for preparing the synthetic chiral camphor type beta-diketone according to claim 1, which is characterized in that:
the specific process of the step 2 is as follows:
pouring the product obtained in the step 1 into a beaker filled with ice water, dropwise adding hydrochloric acid to adjust Ph value to be acidic, pouring into a separating funnel, extracting with diethyl ether, and combining diethyl ether layers; then, the diethyl ether layer is sequentially washed in sodium bicarbonate solution and saturated salt solution, then washed in deionized water, finally dried by adding anhydrous magnesium sulfate, the solvent is distilled off in a rotary way, and separation and purification are carried out by using a silica gel chromatographic column to obtain orange liquid, namely D/L-3-trifluoroacetyl camphor D/L-TFC.
5. The preparation of a novel synthetic chiral camphor type beta-diketone according to claim 4, which is characterized in that: in the step 2, the rotary steaming temperature is 30-35 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310556398.6A CN116730811A (en) | 2023-05-17 | 2023-05-17 | Preparation method of synthetic chiral camphor type beta-diketone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310556398.6A CN116730811A (en) | 2023-05-17 | 2023-05-17 | Preparation method of synthetic chiral camphor type beta-diketone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116730811A true CN116730811A (en) | 2023-09-12 |
Family
ID=87917758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310556398.6A Pending CN116730811A (en) | 2023-05-17 | 2023-05-17 | Preparation method of synthetic chiral camphor type beta-diketone |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116730811A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58152831A (en) * | 1982-03-08 | 1983-09-10 | Daikin Ind Ltd | Production of fluorodiketones |
-
2023
- 2023-05-17 CN CN202310556398.6A patent/CN116730811A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58152831A (en) * | 1982-03-08 | 1983-09-10 | Daikin Ind Ltd | Production of fluorodiketones |
Non-Patent Citations (3)
| Title |
|---|
| JEN-HAI LIAO，等: "Oxidation of Alkenes and Sulfides with Transition Metal Catalysts", JOURNAL OF THE CHINESE CHEMICAL SOCIETY, vol. 42, 31 December 1995 (1995-12-31), pages 850 * |
| LUO KAIJUN，等: "Cyclometalated platinum(II) complexes with sterically bulky camphor-derived groups as β-diketonate ancillary ligand: a new route to efficiently reducing π-π interactions and Pt−Pt interactions", SCI CHINA CHEM, vol. 53, no. 1, 31 January 2010 (2010-01-31) * |
| 谢运，等: "系列樟脑型β － 二酮化合物的合成", 四川师范大学学报( 自然科学版), vol. 34, no. 1, 31 January 2011 (2011-01-31) * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Hirsch et al. | Base-catalyzed alkylation of cyclopentadiene rings with alcohols and amines | |
| CN110540549A (en) | Coumarin group bridged silane and preparation method thereof | |
| CN114315776A (en) | Method for preparing 2, 4-disubstituted tetrahydropyrane compound through hydrogenolysis reaction | |
| CN103724151B (en) | Method for synthesizing 9-aryl fluorene compound | |
| CN116730811A (en) | Preparation method of synthetic chiral camphor type beta-diketone | |
| CN106946705B (en) | Method for synthesizing (1R,2S) -methyl dihydrojasmonate | |
| CN111229312B (en) | Solvent-free catalyst and preparation method and application thereof | |
| Hanselmann et al. | Enantioselective Synthesis of a Wieland-Miescher Ketone Bearing an Angular Hydroxymethyl Group | |
| CN110790737B (en) | Preparation method of 2, 3-dihydro-3, 5-dihydroxy-6-ethyl-4H-pyran-4-one | |
| CN111205184A (en) | Method for synthesizing (9Z,12E) -tetradeca-9, 12-diene-1-alcohol acetate | |
| US4594456A (en) | Racemic and optically active 3-hydroxy-alpha-cyclocitral, its acetals and optically active 3-oxo-alpha-cyclocitral acetals, and their preparation | |
| CN107603271B (en) | Preparation method of long-chain alkoxy BODIPY compound | |
| CN110950739A (en) | Method for directly fluorinating ortho-position of phenol compound | |
| CN116041725B (en) | Preparation method and application of half sandwich structure organic metal supermolecular material | |
| CN111057039B (en) | 5-azido-5-fluoro-1, 3-dioxygen cyclic group-2-ketone derivative and preparation method thereof | |
| CN114149311B (en) | Method for preparing 4-hydroxybenzophenone compound by taking p-methylene quinone as substrate | |
| Fronza et al. | Stereochemistry of the baker's yeast mediated reduction of the C [double bond, length half m-dash] C bond of (Z)-and (E)-5-benzoyloxyhex-3-en-2-one | |
| CN109438183B (en) | Synthesis method of bisabolene | |
| CN113929714B (en) | Preparation method of chiral benzyl silane compound | |
| CN114853707B (en) | Method for synthesizing difluoro hydrogen methylation 2, 3-dihydro benzopyran-4-ketone derivative | |
| CN115246806B (en) | New preparation method of vitamin E | |
| CN114380661B (en) | Synthetic method of (+/-) -lavender alcohol | |
| CN114308111B (en) | Preparation method and application of alkaline solid catalyst | |
| CN112441997B (en) | Method for synthesizing alpha- (2-tetrahydrofuryl) -acetophenone compound | |
| KR100878363B1 (en) | Novel synthesizing method for xanthorrihizol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |