CN108017582A - A kind of synthetic method of brominated 1,3- isoquinolin derovatives - Google Patents
A kind of synthetic method of brominated 1,3- isoquinolin derovatives Download PDFInfo
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- CN108017582A CN108017582A CN201810084382.9A CN201810084382A CN108017582A CN 108017582 A CN108017582 A CN 108017582A CN 201810084382 A CN201810084382 A CN 201810084382A CN 108017582 A CN108017582 A CN 108017582A
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- brominated
- isoquinolin
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
Abstract
The present invention provides a kind of brominated 1, the synthetic method of 3 isoquinolin derovatives, it is in organic solvent, using N alkyl N isopropenyls benzamide and carbon tetrabromide as raw material, trigger in radical initiator and carry out addition reaction, vacuum distillation removes solvent, column chromatography for separation, up to target product after complete reaction.Reagent price needed for present invention reaction is cheap, and environmental pollution is small, and production cost is low, and reactions steps are brief, mild condition, and post processing is simple, industrial production cost can be effectively reduced, suitable for industrialized production.
Description
Technical field
The present invention relates to a kind of synthetic method of brominated 1,3- isoquinolin derovatives, belongs to chemical synthesising technology neck
Domain.
Background technology
1,3- isoquinolin cyclohexadione compounds are widely present in alkaloid, natural products and medicine, are a kind of common doctors
The intermediate of medicinal herb grower's medicine；With analgesia, antitumor and other effects, it may also be used among HIV-1 integrase inhibitors.Bromine is incorporated into
In 1,3- isoquinolin cyclohexadione compounds, it on the one hand may strengthen or new physiological activity is provided for it；On the other hand also it is 1,
The further modification of 3- isoquinolin diketone skeletons provides a variety of possibilities with conversion.Above-mentioned brominated 1,3- isoquinolin diones
The structural formula of compound is as follows：
Wherein, R1For hydrogen, alkyl, halogen, alkoxy, trifluoromethyl, nitro, ester group, cyano group or aromatic radical；R2For alkyl or virtue
Perfume base.
The synthesis 1 of domestic and foreign literature report, the method for 3- isoquinolin derovatives is very much, is mainly the following：（1）
The nonmetallic aryl fluoromethylation of activated olefins.（Wangqing Kong.； Maria Casimiro.；Noelia
Fuentes.；Estibaliz Merino and Cristina Nevado.Angew. Chem. Int. Ed. 2013, 52,
13086 –13090）（2）Metal-free α, beta-unsaturated acyl imines trifluoromethylation.(Lei Li, Min Deng,
Sheng-CaiZheng, Ya-Ping Xiong, Bin Tan and Xin-Yuan Liu.Org.Lett. 2014, 16,
504 507.) α under (3) visible light-inducing, beta-unsaturated acyl imines trifluoromethylation.(LeweiZheng, Chao Yang,
ZhaoZhongXu, FeiGao, and Wujiong XiaJ. Org. Chem.2015, 80, 5730−5736.)（4）It is logical
Cross the Cyclization perfluor isoquinolin of alkene under radiation of visible light.(Shi Tang, You-Lin Deng,JieLi,Wen-
XinWang,Guo-Liang Ding,Ming-Wei Wang, Zhu-Ping Xiao,Ying-Chun Wang and Rui-
Long Sheng.J. Org. Chem.The benzamide of 2015,80,12599 12605.) (5) free radical mediateds is to perfluor
Or the isoquinolin diverging cyclization of cyaniding.(You-Lin Deng,ShiTang,Guo-Liang Ding,Ming-Wei Wang,
JieLi,Zeng-Zeng Li, Li Yuan and Rui-Long Sheng.Org. Biomol. Chem., 2016, 14,
9348-9353.) the free radical cascade fluoroalkyl/cyclisation ethyl bromide difluoride and acrylamide of (6) palladium chtalyst.
(Xiao-Feng Xia, Su-Li Zhu,Yuan Li and Haijun Wang.RSC Adv., 2016, 6, 51703–
51709.) (7) prepare 1,3- isoquinolin diketone derivatives using methacryl yl-benzamide and benzylalcohol and sodium phenylsulfinate
Thing.(Qiujie Tang , Ping Xie , Jin Wang , Jiajun Lin , ChunlaiFeng, Charles U.
Pittman Jr,Aihua Zhou.Tetrahedron 2017,73 ,5436-5443)（8）Substitute the level of n- alkenyl benzamides
Join alkylated reaction.(Ping Qian, Bingnan Du, Wei Jiao, Haibo Mei, Jianlin Han and Yi
Pan.Beilstein J. Org. Chem. 2016,12, 301–308.)（9）Aoxidize decarbonylation coupling fatty aldehyde and metering system
Acid amides prepares 1,3- isoquinolin derovatives.(ChangduoPan,Chaoyue Chen and Jin-Tao Yu.Org.
Biomol. Chem., 2017,15, 1096).The above 1, in the synthetic method of 3- isoquinolin derovatives, there is certain methods
The metallic catalyst and photochemical catalyst of costliness have been used, cost has on the one hand been added, on the other hand also environment is caused very big
Negative effect.These shortcomings cause above synthetic method is applied and popularized in industrial production to receive obstruction.
The content of the invention
In view of the deficiencies of the prior art, it is an object of the present invention to provide a kind of cost it is low, it is environmentally protective, easy to operate and
Suitable for the synthetic method of the brominated 1,3- isoquinolin derovatives of industrialized production.
The method that the present invention synthesizes brominated 1,3- isoquinolin derovatives, is in organic solvent, with N- alkyl-N-
Isopropenyl benzamide and carbon tetrabromide are raw material, trigger in radical initiator and carry out heating reaction to passing through series connection completely
Free radical addition cyclization process after obtain product, after complete reaction vacuum distillation remove solvent, column chromatography for separation, up to mesh
Mark product.
The organic solvent is 1,4- dioxane, methyl phenyl ethers anisole, acetone, tetrahydrofuran or N,N-dimethylformamide.
The molar ratio of substrate N- alkyl-N- isopropenyls benzamide and carbon tetrabromide is 1:1~1:2.
The radical initiator is cumyl hydroperoxide, di-t-butyl peroxide, hydrogen peroxide, m-chloro peroxide benzene first
Acid, Peracetic acid, the hydrogen peroxide tert-butyl alcohol, benzoyl peroxide, carbamide peroxide or peroxidized t-butyl perbenzoate.
The reaction temperature of addition reaction is 30 DEG C ~ 70 DEG C, when the reaction time is 2 ~ 36 small.
The present invention has the following advantages compared with the prior art：
1st, reagent price needed for reaction is cheap, and safe, environmental pollution is small；
2nd, reactions steps are brief, and synthesis condition is gentle, and post processing is simple, and production cost is low；
3rd, reaction rate is very fast, and required time is not grown, and reaction efficiency is high, and reaction yield is high.
Embodiment
It is described further with reference to the synthesis of the instantiation 1,3- isoquinolin derovatives brominated to the present invention.
Embodiment 1：The synthesis of -4 H- isoquinolin -1,3- diketone of 4- bromomethyl -2,4- dimethyl
Magneton is added in 25ml reaction tubes, then sequentially adds raw material N- methyl-N-isopropyl propenylbenzene formamides（0.5mmol）
And carbon tetrabromide（0.75mmol）, 5ml solvents（1,4- dioxane）, the cumyl hydroperoxide of 15%mol, is stirred at 50 DEG C
Mix 2 it is small when；Vacuum distillation carries out column chromatography for separation after removing solvent（Silica gel：200 ~ 300 mesh, eluant, eluent volume ratio are petroleum ether:
Ethyl acetate=15:1）, white powder net product is obtained, is 4- bromomethyl -2,4- dimethyl -4H-isoquinolin -1,3-
Diketone, yield 86%.Its synthesis type is as follows：
Nuclear magnetic data is as follows：1H NMR (600 MHz, CDCl3) δ 8.28 (d, J = 8.6 Hz, 1H), 7.69 (t,J = 8.2 Hz, 1H), 7.50 (t, J = 7.9 Hz, 1H), 7.39 (d, J = 7.9 Hz, 1H), 4.16 (d,J = 9.9 Hz, 1H), 3.67 (d, J = 9.9 Hz, 1H), 3.41 (s, 3H), 1.72 (s, 3H).13C NMR
(151 MHz, CDCl3) δ 174.2, 164.0, 141.1, 134.2, 129.0, 128.1, 125.3, 124.6,
49.1, 40.2, 28.3, 27.3。
Embodiment 2：The synthesis of -2,4,6 trimethyl -4H of 4- bromomethyls-isoquinolin -1,3- diketone
Magneton is added in 25ml reaction tubes, then sequentially adds raw material N- methyl-N-isopropyl acrylic -6- methyl benzamides
（0.5mmol）And carbon tetrabromide（0.75mmol）, 5ml solvents（1,4- dioxane）, the cumyl hydroperoxide of 15%mol,
When stirring 2 is small at 50 DEG C；Vacuum distillation carries out column chromatography for separation after removing solvent（Silica gel：200 ~ 300 mesh, eluant, eluent volume ratio
For petroleum ether:Ethyl acetate=15:1）, white powder net product is obtained, as 4- bromomethyls -2,4,6 trimethyl -4H-different
Quinoline -1,3- diketone, yield 86%, its synthesis type are as follows：
Nuclear magnetic data is as follows：1H NMR (600 MHz, CDCl3) δ 8.16 (d, J = 8.0 Hz, 1H), 7.30(d,
1H), 7.16 (s, 1H), 4.15 (d, J = 9.8 Hz, 1H), 3.66 (d, J = 9.8 Hz, 1H), 3.40
(s, 3H), 2.47 (s, 3H), 1.70 (s, 3H).13C NMR (151 MHz, CDCl3) δ 174.4, 164.0,
145.1, 141.1, 129.18, 129.0, 125.0, 122.9, 49.1, 40.3, 28.3, 27.2, 22.0.
Embodiment 3：The synthesis of -2,4,7 trimethyl -4H of 4- bromomethyls-isoquinolin -1,3- diketone
Magneton is added in 25ml reaction tubes, then sequentially adds raw material N- methyl-N-isopropyl acrylic -7- methyl benzamides
（0.5mmol）And carbon tetrabromide（0.75mmol）, 5ml solvents（1,4- dioxane）, the cumyl hydroperoxide of 15%mol,
When stirring 11 is small at 50 DEG C；Vacuum distillation carries out column chromatography for separation after removing solvent（Silica gel：200 ~ 300 mesh, eluant, eluent volume ratio
For petroleum ether:Ethyl acetate=15:1）, white solid product is obtained, as 4- bromomethyls -2,4,7 trimethyl -4H-isoquinoline
Quinoline -1,3- diketone, yield 94%.Its synthesis type is as follows：
Nuclear magnetic data is as follows：1H NMR (400 MHz, CDCl3) δ 8.08 (s, 1H), 7.49 (d, J = 8.0,
0.5 Hz, 1H), 7.28 (d, J = 8.1 Hz, 1H), 4.14 (d, J = 9.8 Hz, 1H), 3.65 (d, J =
9.8 Hz, 1H), 3.40 (s, 3H), 2.44 (s, 3H), 1.69 (s, 3H).13C NMR (151 MHz, CDCl3)
δ 174.4, 164.1, 138.2, 138.1, 135.2, 129.1, 125.1, 124.5, 48.9, 40.4, 28.2,
27.3, 21.0。
Embodiment 4：The synthesis of -2,4,8 trimethyl -4H of 4- bromomethyls-isoquinolin -1,3- diketone
Magneton is added in 25ml reaction tubes, then sequentially adds raw material N- methyl-N-isopropyl acrylic -8- methyl benzamides
（0.5mmol）And carbon tetrabromide（0.75mmol）, 5ml solvents（1,4- dioxane）, the cumyl hydroperoxide of 15%mol,
When stirring 12 is small at 50 DEG C；Vacuum distillation carries out column chromatography for separation after removing solvent（Silica gel：200 ~ 300 mesh, eluant, eluent volume ratio
For petroleum ether:Ethyl acetate=15:1）, white solid product is obtained, as 4- bromomethyls -2,4,8 trimethyl -4H-isoquinoline
Quinoline -1,3- diketone, yield 85%.Its synthesis type is as follows：
Nuclear magnetic data is as follows：1H NMR (600 MHz, CDCl3) δ 7.52 (t, J = 7.7 Hz, 1H), 7.29 (d,J = 7.4 Hz, 1H), 7.27 (d, J = 7.9 Hz, 1H), 4.17 (d, J = 9.9 Hz, 1H), 3.66 (d,J = 9.9 Hz, 1H), 3.38 (s, 3H), 2.80 (s, 3H), 1.71 (s, 3H).13C NMR (151 MHz,
CDCl3) δ 173.9, 164.4, 142.7, 142.3, 133.0, 132.1, 123.7, 122.9, 49.1, 40.6,
28.7, 27.3, 24.0。
Embodiment 5：The synthesis of bromo- -4 H- isoquinolin -1,3- diketone of -2,4 dimethyl of 4- bromomethyls of 6-
Magneton is added in 25ml reaction tubes, then sequentially adds raw material N- methyl-N-isopropyl acrylic -6- brombenzamides
（0.5mmol）And carbon tetrabromide（0.75mmol）, 5ml solvents（1,4- dioxane）, the cumyl hydroperoxide of 15%mol,
When stirring 11 is small at 50 DEG C；Vacuum distillation carries out column chromatography for separation after removing solvent（Silica gel：200 ~ 300 mesh, eluant, eluent volume ratio
For petroleum ether:Ethyl acetate=15:1）, white solid product is obtained, is bromo- -4 H- of 4- bromomethyls -2,4 dimethyl of 6- different
Quinoline -1,3- diketone, yield 74%.Its synthesis type is as follows：
Nuclear magnetic data is as follows：1H NMR (600 MHz, CDCl3) δ 8.12 (d, J = 8.4 Hz, 1H), 7.62
(dd, J = 8.4, 1.8 Hz, 1H), 7.53 (d, J = 1.8 Hz, 1H), 4.12 (d, J = 10.0 Hz,
1H), 3.60 (d, J = 10.0 Hz, 1H), 3.38 (s, 3H), 1.70 (s, 3H).13C NMR (151 MHz,
CDCl3) δ 173.5, 163.2, 142.8, 131.7, 130.6, 129.4, 128.0, 124.3, 49.1, 39.9,
28.1, 27.4。
Embodiment 6：The synthesis of -2,4 dimethyl -4H of 6- methoxyl group -4- bromomethyls-isoquinolin -1,3- diketone
Magneton is added in 25ml reaction tubes, then sequentially adds raw material N- methyl-N-isopropyl acrylic -6- methoxy benzamides
（0.5mmol）And carbon tetrabromide（0.75mmol）, 5ml solvents（1,4- dioxane）, the cumyl hydroperoxide of 15%mol,
When stirring 4 is small at 50 DEG C；Vacuum distillation carries out column chromatography for separation after removing solvent（Silica gel：200 ~ 300 mesh, eluant, eluent volume ratio
For petroleum ether:Ethyl acetate=15:1）, white solid product is obtained, is 6- methoxyl group -4- bromomethyl -2,4 dimethyl -4H
- isoquinolin -1,3- diketone, yield 92%.Its synthesis type is as follows：
Nuclear magnetic data is as follows：1H NMR (600 MHz, CDCl3) δ 8.22 (d, J = 8.8 Hz, 1H), 7.00 (d,J = 11.2 Hz, 1H), 6.82 (d, J = 2.4 Hz, 1H), 4.14 (d, J = 9.9 Hz, 1H), 3.90
(s, 3H), 3.62 (d, J = 9.8 Hz, 1H), 3.38 (s, 3H), 1.70 (s, 3H).13C NMR (151
MHz, CDCl3) δ 174.3, 164.3, 163.6, 143.3, 131.4, 118.3, 113.5, 110.2, 55.6,
49.3, 40.2, 28.4, 27.1。
Embodiment 7：The synthesis of 4- bromomethyl -2- ethyl -4- methyl -4H- isoquinolin -1,3- diketone
Magneton is added in 25ml reaction tubes, then sequentially adds raw material N- ethyl-N- isopropenyl benzamides（0.5mmol）
And carbon tetrabromide（0.75mmol）, 5ml solvents（1,4- dioxane）, the cumyl hydroperoxide of 15%mol, is stirred at 50 DEG C
Mix 3 it is small when；Vacuum distillation carries out column chromatography for separation after removing solvent（Silica gel：200 ~ 300 mesh, eluant, eluent volume ratio are petroleum ether:
Ethyl acetate=15:1）, colourless oil liquid product is obtained, is 4- bromomethyl -2- ethyl -4- methyl -4H- isoquinolin -1,3-
Diketone, yield 88%.Its synthesis type is as follows：
Nuclear magnetic data is as follows：1H NMR (600 MHz, CDCl3) δ 8.27 (d, J = 7.9, 1.0 Hz, 1H),
7.68 (t, 1H), 7.49 (t, 1H), 7.38 (d, J = 7.9 Hz, 1H), 4.15 (d, J = 9.9 Hz,
1H), 4.09 (dd, J = 7.1, 2.8 Hz, 1H), 4.06 (q, J = 7.1, 1H), 3.65 (d, J = 9.8
Hz, 1H), 1.70 (s, 3H), 1.23 (t, J = 7.1 Hz, 3H).13C NMR (151 MHz, CDCl3) δ
173.7, 163.4, 141.1, 134.1, 129.0, 128.0, 125.5, 124.6, 48.8, 40.5, 35.9,
28.1, 13.0。
Embodiment 8：The synthesis of 4- bromomethyl -2- normal-butyl -4- methyl -4H- isoquinolin -1,3- diketone
Magneton is added in 25ml reaction tubes, then sequentially adds raw material N- normal-butyl-N- isopropenyl benzamides
（0.5mmol）And carbon tetrabromide（0.75mmol）, 5ml solvents（1,4- dioxane）, the cumyl hydroperoxide of 15%mol,
When stirring 3 is small at 50 DEG C；Vacuum distillation carries out column chromatography for separation after removing solvent（Silica gel：200 ~ 300 mesh, eluant, eluent volume ratio
For petroleum ether:Ethyl acetate=15:1）, colourless oil liquid product is obtained, is 4- bromomethyl -2- normal-butyl -4- methyl -4H-
Isoquinolin -1,3- diketone, yield 85%.Its synthesis type is as follows：
Nuclear magnetic data is as follows：1H NMR (600 MHz, CDCl3) δ 8.27 (d, J = 9.0 Hz, 1H), 7.67 (t,J = 8.3 Hz, 1H), 7.49 (t, J = 8.0 Hz, 1H), 7.38 (d, J = 7.9 Hz, 1H), 4.16 (d,J = 9.9 Hz, 1H), 4.07-3.98 (m, 2H), 3.66 (d, J = 9.9 Hz, 1H), 1.70 (s, 3H),
1.66-1.58 (m, 2H), 1.42-1.34 (m, 2H), 0.94 (t, J = 7.4 Hz, 3H).13C NMR (151
MHz, CDCl3) δ 173.9, 163.6, 141.2, 134.1, 129.0, 128.0, 125.5, 124.6, 48.9,
40.6, 40.34, 29.9, 28.3, 20.3, 13.8。
Embodiment 9：The synthesis of 4- bromomethyl -2- phenyl -4- methyl -4H- isoquinolin -1,3- diketone
Magneton is added in 25ml reaction tubes, then sequentially adds raw material N- phenyl-N- isopropenyl benzamides（0.5mmol）
And carbon tetrabromide（0.75mmol）, 5ml solvents（1,4- dioxane）, the cumyl hydroperoxide of 15%mol, is stirred at 50 DEG C
Mix 3 it is small when；Vacuum distillation carries out column chromatography for separation after removing solvent（Silica gel：200 ~ 300 mesh, eluant, eluent volume ratio are petroleum ether:
Ethyl acetate=15:1）, white powdery solids product is obtained, is 4- bromomethyl -2- phenyl -4- methyl -4H- isoquinolin -1,
3- diketone, yield 76%.Its synthesis type is as follows：
Nuclear magnetic data is as follows：1H NMR (600 MHz, cdcl3) δ 8.31 (d, J = 8.8 Hz, 1H), 7.75 (t,J = 8.3 Hz, 1H), 7.57-7.42 (m, 6H), 7.24 (d, J = 7.5 Hz, 1H), 4.19 (d, J =
9.8 Hz, 1H), 3.72 (d, J = 9.8 Hz, 1H), 1.84 (s, 3H).13C NMR (151 MHz, CDCl3) δ
174.2, 163.9, 141.2, 135.3, 134.6, 129.3, 129.3, 128.7, 128.3, 128.25, 125.6,
124.8, 49.4, 41.2, 27.8。
Embodiment 10：The synthesis of 4- bromomethyl -2- benzyl -4- methyl -4H- isoquinolin -1,3- diketone
Magneton is added in 25ml reaction tubes, then sequentially adds starting N-benzyl-N- isopropenyl benzamides（0.5mmol）
And carbon tetrabromide（0.75mmol）, 5ml solvents（1,4- dioxane）, the cumyl hydroperoxide of 15%mol.Stirred at 50 DEG C
Mix 3 it is small when；Vacuum distillation carries out column chromatography for separation after removing solvent（Silica gel：200 ~ 300 mesh, eluant, eluent volume ratio are petroleum ether:
Ethyl acetate=15:1）, white solid product is obtained, is 4- bromomethyl -2- benzyl -4- methyl -4H- isoquinolin -1,3- bis-
Ketone, yield 83%.Its synthesis type is as follows：
Nuclear magnetic data is as follows：1H NMR (600 MHz, CDCl3) δ 8.28 (d, J = 7.9, 1.0 Hz, 1H),
7.69(t, 1H), 7.50 (t, 1H), 7.43 (d, J = 7.2 Hz, 2H), 7.39 (d, J = 7.9 Hz,
1H), 7.29 (t, J = 7.5 Hz, 2H), 7.23 (t, J = 7.3 Hz, 1H), 5.26 (d, J = 14.0
Hz, 1H), 5.19 (d, J = 14.0 Hz, 1H), 4.19 (d, J = 9.9 Hz, 1H), 3.68 (d, J =
9.9 Hz, 1H), 1.70 (s, 3H).13C NMR (151 MHz, CDCl3) δ 174.1, 163.6, 141.2,
136.8, 134.3, 129.2, 128.5, 128.4, 128.1, 127.4, 125.3, 124.6, 49.3, 43.9,
40.0, 28.5。
Claims (6)
1. a kind of synthetic method of brominated 1,3- isoquinolin derovatives, is in organic solvent, with N- alkyl-N- isopropyls
Alkenyl benzamide and carbon tetrabromide are raw material, trigger in radical initiator and carry out addition reaction, depressurize after complete reaction
Solvent, column chromatography for separation, up to target product is distilled off.
2. the synthetic method of brominated 1,3- isoquinolin derovatives as claimed in claim 1, it is characterised in that：Raw material N- hydrocarbon
The structural formula of base-N- isopropenyl benzamides is：
Wherein, R1For hydrogen, alkyl, halogen, alkoxy, trifluoromethyl, nitro, ester group, cyano group or aromatic radical, R2For alkyl, fragrance
Base.
3. the synthetic method of brominated 1,3- isoquinolin derovatives as claimed in claim 1, it is characterised in that：Substrate N- hydrocarbon
The molar ratio of base-N- isopropenyls benzamide and carbon tetrabromide is 1:1~1:2.
4. the synthetic method of brominated 1,3- isoquinolin derovatives as claimed in claim 1, it is characterised in that：It is described organic
Solvent is 1,4- dioxane, methyl phenyl ethers anisole, acetone, tetrahydrofuran or N,N-dimethylformamide.
5. the synthetic method of brominated 1,3- isoquinolin derovatives as claimed in claim 1, it is characterised in that：The freedom
Base initiator is cumyl hydroperoxide, di-t-butyl peroxide, hydrogen peroxide, metachloroperbenzoic acid, Peracetic acid, peroxide
Change the hydrogen tert-butyl alcohol, benzoyl peroxide, carbamide peroxide or peroxidized t-butyl perbenzoate.
6. the synthetic method of brominated 1,3- isoquinolin derovatives as claimed in claim 1, it is characterised in that：Addition reaction
Reaction temperature be 30 DEG C ~ 70 DEG C, the reaction time for 2 ~ 36 it is small when.
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| CN114832862A (en) * | 2022-05-23 | 2022-08-02 | 中国药科大学 | Catalytic composition for coupling reaction and application thereof in preparation of isoquinoline-1, 3-diketone compounds |
| CN115819308A (en) * | 2022-12-08 | 2023-03-21 | 万华化学集团股份有限公司 | Preparation method of cumene hydroperoxide |
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| CN115819308B (en) * | 2022-12-08 | 2024-03-29 | 万华化学集团股份有限公司 | Preparation method of poly-hydrogen peroxide cumene |
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