CN107586285A - A kind of preparation method of the ketone derivatives of 2,3 dihydrobenzopyrans 4 - Google Patents
A kind of preparation method of the ketone derivatives of 2,3 dihydrobenzopyrans 4 Download PDFInfo
- Publication number
- CN107586285A CN107586285A CN201610541013.9A CN201610541013A CN107586285A CN 107586285 A CN107586285 A CN 107586285A CN 201610541013 A CN201610541013 A CN 201610541013A CN 107586285 A CN107586285 A CN 107586285A
- Authority
- CN
- China
- Prior art keywords
- dihydrobenzopyrans
- preparation
- ketone derivatives
- solvent
- reaction
- 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.)
- Granted
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention provides the preparation method that one kind prepares the ketone derivatives of 2,3 dihydrobenzopyrans 4, comprise the following steps：In nitrogen atmosphere, at room temperature by the adjacent acrylic epoxide benzaldehyde derivative shown in formula (I) and the dissolving of the Benzoin derivative shown in formula (II) in organic solvent, after addition sensitising agent is well mixed, it is placed under uviol lamp after illumination reaction, through silica gel column chromatography separating purification after revolving removal solvent, products therefrom is the ketone derivatives of 2,3 dihydrobenzopyrans 4.Preparation method of the present invention solves the problems, such as existing synthetic method complex steps, low yield, method feature of environmental protection difference, it can react at normal temperatures and pressures, reaction condition is gentle, without transition metal-catalyzed, with simple to operate, pollution-free, safety and environmental protection, low cost and other advantages.Wherein, R1、R2For hydrogen, halogen or alkyl.
Description
Technical field
The invention belongs to organic synthesis field, and in particular to the preparation of one kind 2,3- dihydrobenzopyrans -4- ketone derivatives
Method.
Background technology
Dihydrobenzopyrans -4- ketone carbon skeletons widely exist in the natural products with bioactivity and some are non-
In native compound.Such as following formula, compound 1-4 is that typically have biology living containing dihydrobenzopyrans -4- ketone carbon skeletons
The natural products of property.According to the literature, a series of 2,3- dihydrobenzopyrans -4- ketone derivatives have multiple biological activities,
Such as following formula: compound 5-6, they are a kind of SIRT2 selective depressants, therefore 2,3- dihydrobenzopyrans -4- ketone derivatives
Synthesis, obtains the extensive concern of chemists.
At present, it is more to synthesize 2,3- dihydrobenzopyrans -4- ketone derivatives report, but existing synthetic method uses mostly
Lewis acid or transition metal-catalyzed system, this just inevitably produces greatly pollution and destroyed to environment, and step
It is cumbersome.Therefore, seek to a kind of 2,3- dihydrobenzopyrans -4- ketone green, that method is simple, step is few and yield is high to spread out
The synthetic method of biology is current urgent problem to be solved.
The content of the invention
The invention provides the method that one kind prepares 2,3- dihydrobenzopyrans -4- ketone derivatives, comprise the following steps：
In a nitrogen atmosphere, at room temperature by shown in the adjacent acrylic epoxide benzaldehyde derivative shown in formula (I) and formula (II)
Benzoin derivative dissolving in organic solvent, add sensitising agent it is well mixed after, be placed under uviol lamp after illumination reaction,
Through silica gel column chromatography separating purification after revolving removal solvent, products therefrom is 2,3- dihydrobenzopyrans -4- ketone derivatives
(shown in formula (III)), reaction equation is as follows：
Wherein, R1、R2For hydrogen, halogen or alkyl.
Preferably, the sensitising agent is benzophenone or cumyl peroxide.
Preferably, the organic solvent is in acetonitrile, benzene, toluene, dimethyl sulfoxide (DMSO) and DMF
One kind.
It is further preferred that the organic solvent is benzene, and when selection benzene makees solvent, product yield highest.
Preferably, the time of the ultraviolet light reaction is 24-48h, the ultraviolet light time is too short, then reacts not
Completely；Irradiation time is long, and product is degraded, and product purity and yield reduce.
Preferably, the silica gel column chromatography separating purification solvent for use is the mixed solvent of petroleum ether and ethyl acetate,
The volume ratio of the petroleum ether and ethyl acetate is 10-50:1.
Preferably, the throwing of the adjacent acrylic epoxide benzaldehyde derivative, Benzoin derivative compound and sensitising agent
It is 1 to expect mol ratio：2-4：4-8.
It is further preferred that the adjacent acrylic epoxide benzaldehyde derivative, Benzoin derivative compound and sensitising agent feed intake
Mol ratio is 1：2：4.
Preferably, the volume that feeds intake of the organic solvent is 50-150mL/mol neighbour's acrylic epoxide benzaldehyde-derivative
Thing.
Beneficial effects of the present invention are：
The invention provides a kind of succinct one-step synthesis 2, the method for 3- dihydrobenzopyrans -4- ketone derivatives, the party
Method solve cumbersome existing 2,3- dihydrobenzopyrans -4- ketone derivatives synthesis steps, low yield, the method feature of environmental protection difference ask
Topic, this method can react at normal temperatures and pressures, and reaction condition is gentle, without transition metal-catalyzed, have it is simple to operate, without dirt
Dye, safety and environmental protection, low cost and other advantages.
Embodiment
Below by specific embodiment, technical scheme is described in further detail.
Embodiment 1
Into 50mL light reaction pipes, adjacent acrylic epoxide benzaldehyde (0.1mmol), styrax are sequentially added
After (0.2mmol), cumyl peroxide (DCP) (0.4mmol), dry benzene (15mL), with nitrogen ball bubbling deoxygenation 0.5h,
Then, reaction system is sealed, is put under 350nm ultraviolet lights and irradiates 24h.After reaction terminates, the rotated evaporimeter of reaction dissolvent
After concentration is spin-dried for, then using volume ratio as 50:1 petroleum ether：The mixed solution of ethyl acetate carries out silica gel column layer as eluant, eluent
Purifies and separates are analysed, obtain corresponding 3- phenacyls -2,3- dihydrobenzopyrans -4- ketone, its structural formula is：
Purity 99%, yield 77%, the analysis of its nuclear magnetic data are：1H NMR (400MHz, CDCl3) δ 8.03 (d, J=
7.9Hz, 2H), 7.94 (d, J=7.8Hz, 1H), 7.61 (t, J=7.0Hz, 1H), 7.50 (dd, J=10.4,4.8Hz, 3H),
7.09-6.99 (m, 2H), 4.67 (dd, J=11.1,5.3Hz, 1H), 4.34 (t, J=11.4Hz, 1H), 3.77-3.71 (m,
1H), 3.62 (ddd, J=12.0,8.6,4.6Hz, 1H), 3.05 (dd, J=18.0,8.3Hz, 1H) ppm.
13C NMR(150MHz,CDCl3)δ197.03,193.48,161.86,136.43,136.05,133.51,
128.74,128.18,127.42,121.49,120.66,117.92,70.42,41.86,34.36
Embodiment 2
Into 50mL light reaction pipes, 5- methyl -2- acrylic epoxide benzaldehydes (0.1mmol), styrax are sequentially added
After (0.3mmol), cumyl peroxide (DCP) (0.5mmol), dry acetonitrile (5mL), with nitrogen ball bubbling deoxygenation
0.5h, then, reaction system is sealed, be put under 350nm ultraviolet lights and irradiate 36h.After reaction terminates, the rotated steaming of reaction dissolvent
After hair instrument concentration is spin-dried for, then using volume ratio as 30:1 petroleum ether：The mixed solution of ethyl acetate carries out silica gel as eluant, eluent
Column chromatography purifies and separates, obtain corresponding 3- phenacyls -6- methyl -2,3- dihydrobenzopyrans -4- ketone, its structural formula
For：
Purity 98%, yield 71%.Its nuclear magnetic data is：1H NMR (400MHz, CDCl3) δ 8.00 (d, J=7.3Hz,
2H), 7.70 (s, 1H), 7.59 (t, J=7.4Hz, 1H), 7.48 (t, J=7.6Hz, 2H), 7.30 (dd, J=8.4,1.9Hz,
1H), 6.89 (d, J=8.4Hz, 1H), 4.61 (dd, J=11.1,5.2Hz, 1H), 4.28 (t, J=11.3Hz, 1H), 3.70
(dd, J=18.0,3.7Hz, 1H), 3.61-3.52 (m, 1H), 3.02 (dd, J=18.0,8.4Hz, 1H), 2.31 (s, 3H)
ppm.
13C NMR(150MHz,CDCl3)δ197.11,193.72,159.93,137.13,136.46,133.48,
130.93,128.73,128.18,126.95,120.26,117.69,70.42,41.90,34.46,20.45
Embodiment 3
Into 50mL light reaction pipes, 5- chloro-2-propene base epoxide benzaldehydes (0.1mmol), styrax are sequentially added
After (0.4mmol), cumyl peroxide (DCP) (0.6mmol), dry dimethyl sulfoxide (DMSO) (15mL), with nitrogen ball bubbling
Deoxygenation 0.5h, then, reaction system is sealed, be put under 350nm ultraviolet lights and irradiate 30h.After reaction terminates, reaction dissolvent is through rotation
Turn after evaporimeter concentration is spin-dried for, then using volume ratio as 10:1 petroleum ether：The mixed solution of ethyl acetate is carried out as eluant, eluent
Silica gel column chromatography purifies and separates, obtain chloro- 2, the 3- dihydrobenzopyrans -4- ketone of corresponding 3- phenacyls -6-, its structural formula
For：
Purity 99%, yield 84%.Its nuclear magnetic data is：1H NMR (400MHz, CDCl3) δ 8.00 (d, J=7.4Hz,
2H), 7.87 (d, J=2.6Hz, 1H), 7.60 (t, J=7.4Hz, 1H), 7.49 (t, J=7.6Hz, 2H), 7.43 (dd, J=
8.8,2.6Hz, 1H), 6.96 (d, J=8.8Hz, 1H), 4.65 (dd, J=11.1,5.3Hz, 1H), 4.31 (t, J=11.5Hz,
1H), 3.70 (dd, J=18.1,3.6Hz, 1H), 3.63-3.54 (m, 1H), 3.05 (dd, J=18.1,8.2Hz, 1H) ppm.
13C NMR(151MHz,CDCl3)δ196.74,192.41,160.31,136.30,135.86,133.61,
128.77,128.17,127.02,126.71,121.44,119.68,70.53,41.64,34.26ppm.
Embodiment 4
Into 50mL light reaction pipes, the bromo- 2- acrylic epoxide benzaldehydes (0.1mmol) of 5-, styrax are sequentially added
After (0.2mmol), benzophenone (DCP) (0.8mmol), dry DMF (10mL), with nitrogen ball bubbling
Deoxygenation 0.5h, then, reaction system is sealed, be put under 350nm ultraviolet lights and irradiate 24h.After reaction terminates, reaction dissolvent is through rotation
Turn after evaporimeter concentration is spin-dried for, then using volume ratio as 50:1 petroleum ether：The mixed solution of ethyl acetate is carried out as eluant, eluent
Silica gel column chromatography purifies and separates, obtain bromo- 2, the 3- dihydrobenzopyrans -4- ketone of corresponding 3- phenacyls -6-, its structural formula
For：
Purity 99%, yield 50%.Its nuclear magnetic data is：1H NMR (400MHz, CDCl3) δ 8.03 (d, J=8.9Hz,
3H), 7.61 (t, J=17.3,8.8Hz, 2H), 7.51 (t, J=7.6Hz, 2H), 6.93 (d, J=8.9Hz, 1H), 4.68 (dd,
J=11.1,5.2Hz, 1H), 4.34 (t, J=11.4Hz, 1H), 3.77-3.69 (m, 1H), 3.65-3.56 (m, 1H), 3.07
(dd, J=18.2,8.1Hz, 1H) ppm.
13C NMR(150MHz,CDCl3)δ196.72,192.27,160.77,138.64,136.30,133.62,
129.84,128.78,128.17,121.93,120.03,114.16,70.50,41.59,34.26ppm.
Embodiment 5
Into 50mL light reaction pipes, sequentially add 3,5- dimethyl -2- acrylic epoxide benzaldehydes (0.1mmol), rest in peace
, then, will be anti-with nitrogen ball bubbling deoxygenation 0.5h after fragrant (0.3mmol), benzophenone (0.8mmol), dry benzene (15mL)
Answer system to seal, be put under 350nm ultraviolet lights and irradiate 48h.After reaction terminates, the rotated evaporimeter concentration of reaction dissolvent is spin-dried for
Afterwards, then using volume ratio as 40:1 petroleum ether：The mixed solution of ethyl acetate carries out silica gel column chromatography purifying point as eluant, eluent
From obtaining corresponding 3- phenacyls -6,8- dimethyl -2,3- dihydrobenzopyrans -4- ketone, its structural formula is：
Purity 97.5%, yield 58%.Its nuclear magnetic data is：1H NMR (400MHz, CDCl3) δ 8.03 (d, J=
7.7Hz, 2H), 7.61 (t, 2H), 7.50 (t, J=7.5Hz, 2H), 7.20 (s, 1H), 4.68 (dd, J=10.9,5.1Hz,
1H), 4.29 (t, J=11.2Hz, 1H), 3.73 (d, J=18.1Hz, 1H), 3.61-3.52 (m, 1H), 3.03 (dd, J=
17.9,8.5Hz,1H),2.30(s,3H),2.24(s,3H)ppm.13C NMR(150MHz,CDCl3)δ197.18,194.08,
158.22,138.10,136.51,133.44,130.17,128.70,128.18,126.92,124.47,119.92,70.28,
41.74,34.49,20.42,15.55ppm.
Embodiment 6
Into 50mL light reaction pipes, 2- acrylic epoxide benzaldehydes (0.1mmol), 4 are sequentially added, the substitution of 4 '-diformazan
After styrax (0.4mmol), cumyl peroxide (DCP) (0.4mmol), dry benzene (15mL), removed with nitrogen ball bubbling
Oxygen 0.5h, then, reaction system is sealed, be put under 350nm ultraviolet lights and irradiate 24h.After reaction terminates, reaction dissolvent is rotated
After evaporimeter concentration is spin-dried for, then with volume ratio
For 40:1 petroleum ether：The mixed solution of ethyl acetate carries out silica gel column chromatography purifies and separates, obtained as eluant, eluent
It is to methylphenacyl group -2,3- dihydrobenzopyrans -4- ketone, its structural formula to corresponding 3-：
Purity 98.2%, yield 64%.Its nuclear magnetic data is：1H NMR (400MHz, CDCl3) δ 7.93 (d, J=
6.3Hz, 3H), 7.51 (t, J=7.6Hz, 1H), 7.30 (d, J=8.8Hz, 2H), 7.09-6.99 (m, 2H), 4.67 (dd, J=
11.1,5.3Hz, 1H), 4.33 (t, J=11.3Hz, 1H), 3.72 (d, J=18.1Hz, 1H), 3.66-3.56 (m, 1H), 3.03
(dd, J=17.8,8.5Hz, 1H), 2.45 (s, 3H) ppm.
13C NMR(150MHz,CDCl3)δ196.64,193.57,161.87,144.37,136.01,133.98,
129.41,128.30,127.42,121.46,120.69,117.91,70.46,41.88,34.24,21.72ppm.
Embodiment 7
Into 50mL light reaction pipes, 2- acrylic epoxide benzaldehydes (0.1mmol), 4 are sequentially added, the substitution of 4 '-dibromo
After styrax (0.2mmol), cumyl peroxide (DCP) (0.4mmol), dry benzene (15mL), removed with nitrogen ball bubbling
Oxygen 0.5h, then, reaction system is sealed, be put under 350nm ultraviolet lights and irradiate 24h.After reaction terminates, reaction dissolvent is rotated
After evaporimeter concentration is spin-dried for, then using volume ratio as 40:1 petroleum ether：The mixed solution of ethyl acetate carries out silicon as eluant, eluent
Gel column chromatography eluting separation, obtain corresponding 3- is to Bromophenac rLl -2,3- dihydrobenzopyrans -4- ketone, its structural formula：
The yield 84% of purity 96.3%.Its nuclear magnetic data is：1H NMR (600MHz, CDCl3) δ 7.91 (dd, J=7.8,
1.2Hz, 1H), 7.87 (d, J=8.5Hz, 2H), 7.63 (d, J=8.5Hz, 2H), 7.52-7.48 (m, 1H), 7.04 (t, J=
7.5Hz, 1H), 7.00 (d, J=8.3Hz, 1H), 4.64 (dd, J=11.1,5.3Hz, 1H), 4.31 (t, J=11.4Hz, 1H),
3.67 (dd, J=17.9,3.9Hz, 1H), 3.63-3.57 (m, 1H), 2.97 (dd, J=17.9,8.0Hz, 1H) ppm.13C
NMR(150MHz,CDCl3)δ196.05,193.31,161.84,136.13,135.16,132.07,129.70,128.74,
127.42,121.55,120.59,117.93,70.36,41.85,34.31ppm.
Embodiment described above is a kind of preferable scheme of the present invention, not the present invention is made any formal
Limitation, there are other variants and remodeling on the premise of without departing from the technical scheme described in claim.
Claims (8)
1. one kind 2, the preparation method of 3- dihydrobenzopyrans -4- ketone derivatives, it is characterised in that the preparation method is included such as
Lower step：
In a nitrogen atmosphere, at room temperature by the adjacent acrylic epoxide benzaldehyde derivative shown in formula (I) and the peace shown in formula (II)
Cease fragrant derivative dissolving in organic solvent, after addition sensitising agent is well mixed, be placed under uviol lamp after illumination reaction, rotate
Through silica gel column chromatography separating purification after removal solvent, products therefrom is 2,3- dihydrobenzopyrans -4- ketone derivatives；
Wherein, R1、R2For hydrogen, halogen or alkyl.
2. 2,3- dihydrobenzopyrans -4- ketone derivatives preparation methods as claimed in claim 1, it is characterised in that the light
Quick dose is benzophenone or cumyl peroxide.
3. 2,3- dihydrobenzopyrans -4- ketone derivatives preparation methods as claimed in claim 1, it is characterised in that described to have
The one kind of solvent in acetonitrile, benzene, toluene, dimethyl sulfoxide (DMSO) and N,N-dimethylformamide.
4. the preparation method of 2,3- dihydrobenzopyrans -4- ketone derivatives as claimed in claim 1, it is characterised in that the purple
The time of outer photo-irradiation reaction is 24-48h.
5. the preparation method of 2,3- dihydrobenzopyrans -4- ketone derivatives as claimed in claim 1, it is characterised in that the silicon
Plastic column chromatography isolates and purifies solvent for use as petroleum ether and the mixed solvent of ethyl acetate, the body of the petroleum ether and ethyl acetate
Product ratio is 10-50:1.
6. the preparation method of 2,3- dihydrobenzopyrans -4- ketone derivatives as claimed in claim 1, it is characterised in that the neighbour
The molar ratio of acrylic epoxide benzaldehyde derivative, Benzoin derivative compound and sensitising agent is 1：2-4：4-8.
7. the preparation method of 2,3- dihydrobenzopyrans -4- ketone derivatives as claimed in claim 6, it is characterised in that the neighbour
The molar ratio of acrylic epoxide benzaldehyde derivative, Benzoin derivative compound and sensitising agent is 1：2：4.
8. the preparation method of 2,3- dihydrobenzopyrans -4- ketone derivatives as claimed in claim 1, it is characterised in that described to have
The volume that feeds intake of solvent is 50-150mL/mmol neighbour's acrylic epoxide benzaldehyde derivative.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610541013.9A CN107586285B (en) | 2016-07-06 | 2016-07-06 | Preparation method of 2, 3-dihydrobenzopyran-4-one derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610541013.9A CN107586285B (en) | 2016-07-06 | 2016-07-06 | Preparation method of 2, 3-dihydrobenzopyran-4-one derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107586285A true CN107586285A (en) | 2018-01-16 |
| CN107586285B CN107586285B (en) | 2020-09-01 |
Family
ID=61046471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610541013.9A Active CN107586285B (en) | 2016-07-06 | 2016-07-06 | Preparation method of 2, 3-dihydrobenzopyran-4-one derivative |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107586285B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111484469A (en) * | 2020-05-14 | 2020-08-04 | 遵义医科大学 | Synthesis method and application of pyran subunit malononitrile photosensitizer lead compound |
| CN112759586A (en) * | 2019-11-01 | 2021-05-07 | 河南大学 | Chiral thiochroman-4-ketone compound, and preparation method and application thereof |
| CN112759580A (en) * | 2019-11-01 | 2021-05-07 | 河南大学 | Preparation method of chroman-4-one and derivatives thereof |
| CN114478449A (en) * | 2022-01-19 | 2022-05-13 | 江苏海洋大学 | Polysubstituted selenium-containing dihydroisobenzofuran derivative and preparation method thereof |
| CN114853707A (en) * | 2022-06-13 | 2022-08-05 | 上饶师范学院 | Method for synthesizing difluoro-hydrogen methylated 2, 3-dihydrobenzopyran-4-ketone derivative |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3126014A1 (en) * | 1981-07-02 | 1983-01-20 | Dynamit Nobel Ag, 5210 Troisdorf | Process for the preparation of chromone |
| US5552551A (en) * | 1992-04-27 | 1996-09-03 | Florida State University | Proton-transfer, low self-absorbing chromophores for use in scintillators |
| WO2002060888A1 (en) * | 2001-01-30 | 2002-08-08 | Pfizer Products Inc. | Processes for preparing chromanylbenzoic acids |
| CN101492424A (en) * | 2009-03-06 | 2009-07-29 | 北京工业大学 | Actinochemical synthesis of 1H-imidazole-5-carboxylic acid ester compounds |
| CN103214446A (en) * | 2013-04-27 | 2013-07-24 | 桂林理工大学 | Asymmetric synthesis method of chromanones derivate |
-
2016
- 2016-07-06 CN CN201610541013.9A patent/CN107586285B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3126014A1 (en) * | 1981-07-02 | 1983-01-20 | Dynamit Nobel Ag, 5210 Troisdorf | Process for the preparation of chromone |
| US5552551A (en) * | 1992-04-27 | 1996-09-03 | Florida State University | Proton-transfer, low self-absorbing chromophores for use in scintillators |
| WO2002060888A1 (en) * | 2001-01-30 | 2002-08-08 | Pfizer Products Inc. | Processes for preparing chromanylbenzoic acids |
| CN101492424A (en) * | 2009-03-06 | 2009-07-29 | 北京工业大学 | Actinochemical synthesis of 1H-imidazole-5-carboxylic acid ester compounds |
| CN103214446A (en) * | 2013-04-27 | 2013-07-24 | 桂林理工大学 | Asymmetric synthesis method of chromanones derivate |
Non-Patent Citations (6)
| Title |
|---|
| AKKATTU T. BIJU等: "N-Heterocyclic Carbene-Catalyzed Cascade Reaction Involving the Hydroacylation of Unactivated Alkynes", 《J. AM. CHEM. SOC.》 * |
| ANDREY A. FOKIN等: "Selective Alkane Transformations via Radicals and Radical Cations: Insights into the Activation Step from Experiment and Theory", 《CHEM. REV.》 * |
| JAVIER READ DE ALANIZ等: "Scope of the Asymmetric Intramolecular Stetter Reaction Catalyzed by Chiral Nucleophilic Triazolinylidene Carbenes", 《J. ORG. CHEM.》 * |
| JOHANNES F. FRANZ等: "A versatile combined N-heterocyclic carbene and base-catalyzed multiple cascade approach for the synthesis of functionalized benzofuran-3-(2H)-ones", 《TETRAHEDRON LETTERS》 * |
| KENTARO ASAHI等: "Facile Endoperoxypropellane Synthesis by Manganese(III) Acetate-Mediated Aerobic Oxidation", 《EUR. J. ORG. CHEM.》 * |
| 王德中等: "《功能高分子材料》", 31 August 1998, 中国物资出版社 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112759586A (en) * | 2019-11-01 | 2021-05-07 | 河南大学 | Chiral thiochroman-4-ketone compound, and preparation method and application thereof |
| CN112759580A (en) * | 2019-11-01 | 2021-05-07 | 河南大学 | Preparation method of chroman-4-one and derivatives thereof |
| CN111484469A (en) * | 2020-05-14 | 2020-08-04 | 遵义医科大学 | Synthesis method and application of pyran subunit malononitrile photosensitizer lead compound |
| CN111484469B (en) * | 2020-05-14 | 2022-07-05 | 遵义医科大学 | Synthesis method and application of pyran subunit malononitrile photosensitizer lead compound |
| CN114478449A (en) * | 2022-01-19 | 2022-05-13 | 江苏海洋大学 | Polysubstituted selenium-containing dihydroisobenzofuran derivative and preparation method thereof |
| CN114478449B (en) * | 2022-01-19 | 2023-10-27 | 江苏海洋大学 | Polysubstituted selenium-containing dihydroisobenzofuran derivative and preparation method thereof |
| CN114853707A (en) * | 2022-06-13 | 2022-08-05 | 上饶师范学院 | Method for synthesizing difluoro-hydrogen methylated 2, 3-dihydrobenzopyran-4-ketone derivative |
| CN114853707B (en) * | 2022-06-13 | 2024-01-26 | 上饶师范学院 | Method for synthesizing difluoro hydrogen methylation 2, 3-dihydro benzopyran-4-ketone derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107586285B (en) | 2020-09-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107586285A (en) | A kind of preparation method of the ketone derivatives of 2,3 dihydrobenzopyrans 4 | |
| Rueping et al. | Enantioselective Organocatalytic Reactions of 4‐Hydroxycoumarin and 4‐Hydroxypyrone with α, β‐Unsaturated Aldehydes–An Efficient Michael Addition‐Acetalization Cascade to Chromenones, Quinolinones and Pyranones | |
| CN109912503B (en) | Synthetic method of 2, 3-diacyl quinoline compound | |
| CN110386885B (en) | Preparation method of visible light promoted beta-carbonyl sulfone compound | |
| CN110845428B (en) | Photocatalytic preparation method of 3-acyl quinoxalinone compound | |
| CN109180625B (en) | Preparation method of seleno-flavonoid compound | |
| CN107445969B (en) | A kind of tricyclic indole derivatives and its preparation and application | |
| CN106117216A (en) | A kind of method of atmospheric high efficiency synthesis 6H iso-indoles [2,1 a] indole 6 ketone compounds | |
| CN102126942B (en) | Method for synthesizing hypericin | |
| CN108727385B (en) | Preparation method of polysubstituted dihydropyrimido indolone derivative | |
| CN105985290B (en) | Cross coupling method of ether compound and isoquinoline derivative | |
| CN102584760B (en) | Enantiomorphous-kaurene diterpene and derivative and preparation method thereof | |
| CN107312024A (en) | Photoinduction carbon monoxide-releasing molecules and preparation method thereof | |
| CN103739608B (en) | The residue utilizing sweet wormwood to extract Artemisinin prepares the method for Artemisinin | |
| CN106397381A (en) | 2-alkoxy chromone oxime derivative and preparation method and application thereof | |
| CN109535046B (en) | Preparation method of sulfoxide compound | |
| CN108640807A (en) | A kind of preparation method of formylated Hete rocyclic derivatives | |
| CN110078699B (en) | Synthesis method of C-3 thiocyanate substituted 4-amino coumarin derivative promoted by visible light | |
| CN101270119A (en) | Technique for purifying spherosinin from leguminosae pointvetch or milk vetch | |
| CN105884739A (en) | Synthetic method for benzocoumarin polycyclic compounds | |
| CN106336417B (en) | Substituted furans isoflavonoid derivatives and preparation method thereof | |
| CN106243073B (en) | A kind of 2-H 1-benzopyran derivatives and its synthetic method | |
| CN109942570A (en) | A kind of conjugation microporous polymer based on phenthazine, preparation method and efficient catalytic application | |
| JP2016087506A (en) | Organic compound capturing agent | |
| CN116162076B (en) | Spirocyclic gamma-butyrolactone containing carboxylic acid tert-butyl ester and 1, 3-indene diketone structure and preparation method thereof |
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 | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |