CN118206589A - Chiral separation porous material and preparation method thereof - Google Patents
Chiral separation porous material and preparation method thereof Download PDFInfo
- Publication number
- CN118206589A CN118206589A CN202410314138.2A CN202410314138A CN118206589A CN 118206589 A CN118206589 A CN 118206589A CN 202410314138 A CN202410314138 A CN 202410314138A CN 118206589 A CN118206589 A CN 118206589A
- Authority
- CN
- China
- Prior art keywords
- chiral
- barbituric acid
- stationary phase
- phenylisonitrile
- chiral separation
- 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
- 238000000926 separation method Methods 0.000 title claims abstract description 48
- 239000011148 porous material Substances 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- 239000000463 material Substances 0.000 claims abstract description 56
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 47
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims abstract description 47
- 230000005526 G1 to G0 transition Effects 0.000 claims abstract description 42
- RCIBIGQXGCBBCT-UHFFFAOYSA-N phenyl isocyanide Chemical compound [C-]#[N+]C1=CC=CC=C1 RCIBIGQXGCBBCT-UHFFFAOYSA-N 0.000 claims abstract description 38
- 229920000642 polymer Polymers 0.000 claims abstract description 38
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 30
- 239000003054 catalyst Substances 0.000 claims abstract description 25
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 25
- 229940126062 Compound A Drugs 0.000 claims abstract description 17
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 239000000178 monomer Substances 0.000 claims abstract description 11
- 150000001345 alkine derivatives Chemical class 0.000 claims abstract description 8
- 238000001338 self-assembly Methods 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 50
- -1 alkynyl barbituric acid derivative Chemical compound 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- 229940125717 barbiturate Drugs 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000000945 filler Substances 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000000377 silicon dioxide Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 3
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 3
- 229960005235 piperonyl butoxide Drugs 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 claims description 3
- 235000012239 silicon dioxide Nutrition 0.000 claims 2
- OBFQBDOLCADBTP-UHFFFAOYSA-N aminosilicon Chemical compound [Si]N OBFQBDOLCADBTP-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- 239000013384 organic framework Substances 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 238000001308 synthesis method Methods 0.000 description 6
- UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 description 4
- 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 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229960003433 thalidomide Drugs 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000002296 dynamic light scattering Methods 0.000 description 3
- 150000002527 isonitriles Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000010183 spectrum analysis Methods 0.000 description 3
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- ZINRVIQBCHAZMM-UHFFFAOYSA-N 1-Amino-2,4-dibromoanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC(Br)=C2N ZINRVIQBCHAZMM-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-Phenylethanol Natural products OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- BIOCOYIPJQMGTN-UHFFFAOYSA-N methyl 2-(3-benzoylphenyl)propanoate Chemical compound COC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 BIOCOYIPJQMGTN-UHFFFAOYSA-N 0.000 description 2
- 229960002009 naproxen Drugs 0.000 description 2
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- SYTBZMRGLBWNTM-SNVBAGLBSA-N (R)-flurbiprofen Chemical compound FC1=CC([C@H](C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-SNVBAGLBSA-N 0.000 description 1
- UFDBSQOPFCFANI-UHFFFAOYSA-N 1-n,3-n-bis[6-(butanoylamino)pyridin-2-yl]benzene-1,3-dicarboxamide Chemical compound CCCC(=O)NC1=CC=CC(NC(=O)C=2C=C(C=CC=2)C(=O)NC=2N=C(NC(=O)CCC)C=CC=2)=N1 UFDBSQOPFCFANI-UHFFFAOYSA-N 0.000 description 1
- WGTASENVNYJZBK-UHFFFAOYSA-N 3,4,5-trimethoxyamphetamine Chemical compound COC1=CC(CC(C)N)=CC(OC)=C1OC WGTASENVNYJZBK-UHFFFAOYSA-N 0.000 description 1
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- ZUKOCGMVJUXIJA-UHFFFAOYSA-N 6-chlorohex-1-yne Chemical compound ClCCCCC#C ZUKOCGMVJUXIJA-UHFFFAOYSA-N 0.000 description 1
- GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 206010010356 Congenital anomaly Diseases 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin Chemical group O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 description 1
- 229960002626 clarithromycin Drugs 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000008358 core component Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical compound [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 210000003754 fetus Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000010550 living polymerization reaction Methods 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229960001699 ofloxacin Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000010587 phase diagram Methods 0.000 description 1
- 229940117803 phenethylamine Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000003390 teratogenic effect Effects 0.000 description 1
- MVDRXYIEGOGRAI-UHFFFAOYSA-N tribromomethylbenzene Chemical compound BrC(Br)(Br)C1=CC=CC=C1 MVDRXYIEGOGRAI-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Catalysts (AREA)
Abstract
The invention discloses a chiral separation porous material and a preparation method thereof, wherein the chiral separation porous stationary phase material has the structural general formula ofThe preparation method of the chiral separation porous stationary phase material comprises the following steps of carrying out active polymerization on a phenylisonitrile monomer by using a barbituric acid alkyne palladium catalyst to obtain a phenylisonitrile polymer with barbituric acid at two ends, and adding a compound A, and carrying out self-assembly driven by intermolecular hydrogen bonds of a barbituric acid unit and the compound A to obtain the chiral porous stationary phase material. The preparation method of the chiral porous stationary phase material is simple to operate and easy to synthesize, and has great potential application value in the fields of biomedicine, nanotechnology, intelligent materials, photoelectric materials and the like.
Description
Technical Field
The invention relates to the field of functional polymers and polymer reactions, in particular to a chiral separation porous material and a preparation method thereof.
Background
Chiral drugs refer to a pair of enantiomers of a drug which cannot be overlapped by a guard mirror image of a molecular structure, and are also called drugs containing chiral factors. When chiral drugs are taken into an organism, their pharmacological and physiological effects and their molecular recognition capacity and chiral match with the receptor are related. Chiral drug enantiomers have different stereo configurations, and different enantiomers have stereo selectivity differences in pharmacological activity, metabolism and pharmacokinetics, so that one isomer is often an active ingredient of a drug, and the other isomer is possibly inefficient, ineffective and even harmful to human bodies. The most typical example is clarithromycin, a broad-spectrum antibiotic for malaria treatment. Of the enantiomers, only the D-isomer has insecticidal effect, while the L-isomer is completely ineffective. For example, the drug thalidomide (Thalidomide, also known as reaction arrest), R-form thalidomide is a remarkably effective sedative and analgesic agent, which slows the pregnancy reaction of pregnant women, while S-form thalidomide has a strong teratogenic effect, which can cause severe congenital anomalies and disabilities in the fetus. The S-configuration of ofloxacin as antibacterial agent has high efficacy and basically no toxicity, while the R-configuration enantiomer thereof can damage liver and kidney functions. Among the existing total synthetic drugs on the market, chiral drugs account for about 40%, only a small part of them are sold in the form of single enantiomer, and most of the rest are marketed in the form of racemate, which brings potential threat to patients to some extent and may even cause injury. Therefore, the development of novel chiral separation materials is of great significance.
The chiral supermolecular materials reported at present have few types and relatively single functions, and the development and preparation of novel chiral supermolecular materials are necessary. The core component of the chiral supermolecular material is a chiral helical polymer in the supermolecular material, and proper chiral helical polymer is selected to perform functional design, so that the chiral supermolecular material has important significance in improving the performance and chiral separation capability of the chiral supermolecular material. Among the many helical polymers, polyisonitriles (Poly (isocyanides), PI) were the chiral helical polymers that were originally found to have a stable helical conformation, with a PI conjugated c=n bond on the backbone carbon, which distorts the polymer backbone, thus forming a stable helical structure. Meanwhile, the main chain of the polyisonitrile presents a rigid structure, is introduced into a supermolecular organic framework structure, realizes a novel chiral porous material, gives the novel chiral porous material new properties and functions, and further regulates and controls the chiral separation and other properties of the chiral supermolecular material.
The accurate construction of chiral substances with high optical purity is always the core research content of synthetic chemistry, pharmaceutical chemistry and analytical chemistry. Although asymmetric synthesis has achieved accurate synthesis of a variety of chiral species, chiral separation remains one of the important routes to chiral species. The chiral column separation technology widely used at present has the problems of low separation efficiency, long period, limited applicable chiral molecules and the like.
Disclosure of Invention
The invention aims to provide a chiral separation porous material and a preparation method thereof, wherein the chiral separation porous stationary phase material combines a polyisonitrile with a supermolecule organic framework, has simple operation and easy synthesis, and has great potential value in the fields of fluorescent probes, biomedicine, nanotechnology, intelligent materials, photoelectric materials and the like.
In one aspect of the invention, the invention provides a palladium barbiturate catalyst. According to an embodiment of the invention, the chemical structural formula of the palladium barbiturate catalyst is as follows:
In another aspect of the invention, the invention provides a method for preparing a palladium barbiturate catalyst. According to the embodiment of the invention, the preparation method comprises the following steps of reacting an alkynyl barbituric acid derivative with bis (triethylphosphine) palladium dichloride to obtain the barbituric acid alkyne palladium catalyst, wherein the structural general formula of the alkynyl barbituric acid derivative is as follows:
In another aspect of the invention, the invention provides a preparation method of a phenylisonitrile polymer with barbituric acid at two ends, and according to the embodiment of the invention, the phenylisonitrile polymer with barbituric acid at two ends is obtained by performing active polymerization on a phenylisonitrile monomer by using the palladium barbiturate catalyst.
In addition, the preparation method of the phenylisonitrile polymer with barbituric acid at two ends according to the embodiment of the invention can also have the following additional technical characteristics:
In some embodiments of the invention, the living polymerization is carried out in an anhydrous oxygen-free, nitrogen atmosphere at a reaction temperature of 50-90 ℃ for a reaction time of 6-24 hours; the solvent A is added during the active polymerization reaction, and the solvent A is one or more of tetrahydrofuran, chloroform and toluene; the molar ratio of the palladium catalyst with the palladium alkyne barbiturate and the benzoisonitrile monomer at the two ends is 1: (5-100); when the input amount of the phenylisonitrile monomer is 30-100 mg, the addition amount of the solvent A is 1-3 mL; the phenyl isonitrile monomer Wherein the R substituent is an alkyl chain or an oxygen chain, the number of carbon in the alkyl chain is any number of 2-10, and the number of carbon and oxygen in the oxygen chain is any number of 2-10.
In another aspect of the invention, the invention provides a phenylisonitrile polymer with barbituric acid at both ends. According to the embodiment of the invention, the polymer is prepared by a preparation method of a phenylisonitrile polymer with barbituric acid at two ends, and the phenylisonitrile polymer with barbituric acid at two ends has the following chemical structural general formula:
wherein R is alkyl chain or oxygen chain, the number of carbon in the alkyl chain is any number in 2-10, the number of carbon and oxygen in the oxygen chain is any number in 2-10, and the polymerization degree m=any number in 5-100.
In another aspect of the present invention, a method for preparing a chiral separation porous stationary phase material is provided. According to the embodiment of the invention, the phenylisonitrile polymer with barbituric acid at two ends and the compound A are added into the reagent A for reaction, and the chiral porous stationary phase material is obtained by self-assembly driven by intermolecular hydrogen bonds between barbituric acid units and the compound A, wherein the reagent A is one or more of tetrahydrofuran, chloroform and toluene. The chemical structure of compound a (5, 5' - (benzene-1, 3, 5-triyltri (methylene)) tris (oxy) tris (N 1,N3 -bis (6-butyramidopyridin-2-yl) isophthalamide)) is as follows:
In addition, the preparation method of the chiral separation porous stationary phase material according to the above embodiment of the present invention may further have the following additional technical features:
In some embodiments of the invention, the reaction is carried out in an anhydrous oxygen-free, nitrogen atmosphere at room temperature for a period of time ranging from 6 to 24 hours; the molar ratio of the phenylisonitrile polymer with barbituric acid at two ends to the compound A is 3:1.
The synthetic route of the chiral separation porous stationary phase material is as follows:
In another aspect of the present invention, a chiral separation porous stationary phase material is provided. According to the embodiment of the invention, the chiral separation porous stationary phase material is prepared according to the preparation method of the chiral separation porous stationary phase material, and the chiral separation porous stationary phase material has the following structural general formula:
Wherein R substituent is alkyl chain or oxygen chain, the number of carbon in the alkyl chain is any number in 2-10, the number of carbon and oxygen in the oxygen chain is any number in 2-10, and the polymerization degree m is any number in 5-100.
In another aspect of the invention, the invention provides a method for preparing a chiral column of a chiral separation porous material. According to the embodiment of the invention, the filler and the chiral separation porous stationary phase material are uniformly stirred and pressurized to 40MPa, so that all the gas is discharged out of the chiral column, and the chiral separation porous material chiral column is obtained.
In addition, the preparation method of the chiral separation porous material chiral column according to the embodiment of the invention can also have the following additional technical characteristics:
in some embodiments of the invention, the filler is one or both of silica, amino silica; the mass ratio of the filler to the chiral separation porous stationary phase material is 10:1.
Compared with the prior art, the invention has the beneficial effects that:
(1) According to the invention, a series of well-defined polyphenyl isonitriles with predictable Mn and very low Mw/Mn are prepared by using a novel palladium barbiturate alkyne catalyst to carry out active polymerization on phenyl isonitrile monomers, and the whole preparation method is simple, has no strict requirements on experimental conditions and is easy to carry out.
(2) The synthetic compound A in the invention is simple in synthesis, and can simply and rapidly obtain chiral porous stationary phase materials.
(3) The phenylisonitrile polymer has wide raw material sources; the catalyst used for catalyzing the reaction of the phenylisonitrile monomer has a plurality of types.
(4) According to the invention, the pore diameter of the chiral porous stationary phase material is controlled according to the difference of polymerization degrees, so that the uniform and adjustable pore diameter is obtained, and the chiral molecules which are difficult to separate are separated by matching the pore diameter with the chiral molecules.
(5) The chiral separation porous stationary phase material combines the isonitrile with the supermolecular organic framework, and has great application value in the fields of fluorescent probes, biomedicine, nanotechnology, intelligent materials, photoelectric materials and the like.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of palladium acetylenic barbiturate catalyst in example 1 of the present invention;
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of phenylisonitrile in example 2 of the present invention;
FIG. 3 is a gel permeation chromatogram of the present invention of example 2 with barbituric acid isonitrile polymer P1 at both ends;
FIG. 4 is a nuclear magnetic resonance hydrogen spectrum of the compound A in example 4 of the present invention;
FIG. 5 is a graph of dynamic light scattering analysis of the organic framework SOFs of the supramolecules of example 5 of the present invention;
FIG. 6 is a nuclear magnetic resonance spectrum of the supermolecular organic framework SOFs before and after assembly in example 5 of the present invention;
FIG. 7 shows a liquid phase diagram of resolution of racemate in example 7 of the present invention, wherein the left diagram shows naproxen methyl ester, ketoprofen methyl ester and phenethyl alcohol ethyl ester from top to bottom, and the right diagram shows phenethylamine, benzoin and naproxen from top to bottom.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and fully with reference to the accompanying drawings, in which it is evident that the embodiments described are only some, but not all embodiments of the invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
The synthesis method of the palladium acetylide barbiturate catalyst comprises the following steps:
(1) Sodium hydride (0.41 g, 60%) was washed with cyclohexane and suspended in DMF, the nitrogen atmosphere was replaced, compound 9 (1.8 g,9.6 mmol) was added dropwise at 0deg.C, after stirring for 20min, the system was free from gas evolution and the solution was gradually clear, 6-chlorohexyne (1.0 g,8.6 mmol) was added dropwise, the reaction system turned yellow, after stirring for 1h at room temperature, the system was transferred to 60deg.C and stirred, after 24h of reaction, TLC followed the progress of the reaction, and the reaction was completed to give compound 10.
(2) Sodium hydride (1.5 g, 60%) was washed with cyclohexane and suspended in DMSO, the nitrogen atmosphere was replaced, urea (1.52 g,18.6 mmol) dissolved in DMSO was added dropwise at 0deg.C, compound 10 was added dropwise, the gas was released, the reaction was transferred to room temperature, and after stirring for 20 hours, TLC followed the progress of the reaction and the reaction was completed to give compound 11.
(3) Synthesis of novel palladium barbiturate alkynes catalyst: compound 11 (60 mg,0.25 mmol), bis (triethylphosphine) palladium dichloride (105.0 mg,0.25 mmol) and CuCl (1.23 mg,0.0125 mmol) were weighed into a double-necked flask, the nitrogen atmosphere was replaced, dichloromethane and triethylamine were added, after 1h, TLC followed the progress of the reaction, and the reaction was completed. Obtaining a novel palladium alkyne barbiturate catalyst, wherein the palladium alkyne barbiturate catalyst has the structural formula of
The route for the synthesis of product 1 of this example is as follows:
Nuclear magnetic hydrogen spectrum analysis was performed on the palladium butoxide catalyst in this example, and a triethyl signal in the palladium butoxide catalyst was observed, and the nuclear magnetic hydrogen spectrum is shown in fig. 1.
Example 2
The synthesis method of the phenylisonitrile polymer P1 with barbituric acid at two ends comprises the following steps:
Phenylisonitrile (100 mg) and the palladium barbiturate catalyst (21.8 mg) prepared in example 1 were put in a polymerization flask, and under anhydrous and anaerobic conditions, vacuum was applied to the flask, nitrogen was introduced, dried chloroform was added, the reaction was refluxed at 55℃for 24 hours, methanol was added to terminate the reaction, and the obtained product was washed with methanol and then dried in vacuo until the quality became unchanged, to obtain a phenylisonitrile polymer P1 having barbituric acid at both ends.
Wherein, the structural general formula of the phenylisonitrile is as follows:
the structural general formula of the polymer P1 with barbituric acid isonitrile at two ends is as follows:
In the/> Wherein m=5 to 100.
The synthetic route for the barbituric acid isonitrile polymer P1 with two ends in this example is as follows:
wherein, the structural general formula of the barbituric acid alkyne palladium catalyst is as follows:
The phenylisonitrile in the embodiment is subjected to nuclear magnetic hydrogen spectrum analysis and gel permeation chromatography analysis of a polymer P1 with barbituric acid isonitrile at two ends, a benzene ring signal in the phenylisonitrile can be observed, and the nuclear magnetic hydrogen spectrum is shown in figure 2; as shown in FIG. 3, the gel permeation chromatograph of the polymer P1 with barbituric acid isonitrile at both ends increases with increasing polymerization degree, and the molecular weight distribution is low.
Example 3
The synthesis method of the phenylisonitrile polymer P2 with barbituric acid at two ends comprises the following steps:
Phenylisonitrile (100 mg) and the palladium barbiturate catalyst (9.9 mg) prepared in example 1 were put in a polymerization flask, the mixture was evacuated and filled with nitrogen under anhydrous and anaerobic conditions, dried chloroform was added, the reaction was refluxed at 55℃for 24 hours, methanol was added to terminate the reaction, and the obtained product was washed with methanol and then dried in vacuo until the quality became unchanged, to obtain a phenylisonitrile polymer P2 having barbituric acid at both ends.
Wherein, the structural general formula of the phenylisonitrile is as follows:
The structural general formula of the polymer P2 with barbituric acid isonitrile at two ends is as follows:
In the/> Wherein m=5 to 100.
The synthetic route for the barbituric acid isonitrile polymer P2 with two ends in this example is as follows:
wherein, the structural general formula of the barbituric acid alkyne palladium catalyst is as follows:
Example 4
The synthesis method of the compound A comprises the following steps:
(1) Synthesis of Compound 2: compound 1 (5 g,0.023 mol), K 2CO3 (3.94 g,0.029 mol) were weighed, nitrogen atmosphere was replaced, CH 3CN/CH3COCH3 (V/V) =1:1 was added into a double-mouth bottle, a reflux device was set up, after refluxing for 0.5h, a pale yellow suspension was obtained, then C 6H5CH2 Cl was added dropwise into the reflux device, after 12h of reaction, TLC followed the progress of reaction, and the reaction was completed, to obtain compound 2.
(2) Synthesis of Compound 3: compound 2 (2 g,6.66 mmol), KOH (14.9 g,0.27 mol) was weighed out, the nitrogen atmosphere was replaced, meOH was added to a double-necked flask and refluxed for 4h, and cooled to room temperature. Adding 2N HCl into the reaction system for acidification to obtain white precipitate, filtering and collecting a precipitate product, and drying to obtain a compound 3.
(3) Synthesis of Compound 4: compound 3 (2 g,0.0073 mol) was weighed into a double-necked flask, purged with nitrogen, and refluxed at 65℃with the addition of SOCl 2. As the reaction proceeded, the reaction system was gradually clarified, after 4 hours of reaction, TLC followed the progress of the reaction, and the reaction was completed to give compound 4.
(4) Synthesis of Compound 5: the compound aminopyridine (2 g,0.018 mol) was weighed into a double-necked flask and dissolved by adding THF to the reaction system, and triethylamine was added to provide a basic environment. The ice bath was cooled to 0 ℃, butyryl chloride (2 g,0.019 mol) was added dropwise over 1h, after 3h reaction at 0 ℃, the system was transferred to room temperature for 24h reaction, and TLC followed the reaction progress and the reaction was completed to give compound 5.
(5) Synthesis of Compound 6: compound 4 (1 g,0.0032 mol), compound 5 (1.37 g,0.0077 mol) and triethylamine were weighed, anhydrous THF and triethylamine were added to the reaction system under nitrogen atmosphere, and after 18h of reaction, TLC followed the progress of the reaction and the reaction was completed to obtain compound 6.
(6) Synthesis of Compound 7: compound 6 (1.5 g) was weighed, pd/C and methanol were added, after 24h of reaction, TLC followed the reaction progress, after the reaction was completed, palladium carbon was removed by suction filtration through celite pad, to obtain compound 7.
(7) Synthesis of Compound 8: compound 7 (360 mg,0.00071 mol), tribromomethylbenzene (84 mg,0.00023 mol), K 2CO3 (98 mg,0.00071 mmol), naI (20 mg,0.00015 mol) were weighed out, an atmosphere of nitrogen was replaced, anhydrous DMF was added, after 18 hours of reaction, TLC followed the progress of the reaction, and the reaction was completed to obtain compound 8, i.e., compound a.
The synthetic route of the compound A is as follows:
the compound a in this example was subjected to nuclear magnetic hydrogen spectrum analysis, and an amino signal in hamilton was observed, and the nuclear magnetic hydrogen spectrum is shown in fig. 4.
Example 5
A chiral separation porous material and a synthesis method thereof comprise the following steps:
The compound A (20 mg) prepared in example 4 and the barbituric acid isonitrile polymer P1 (80 mg) prepared in example 2 with two ends are added into a polymerization bottle, under the anhydrous and anaerobic condition, vacuum pumping and nitrogen charging are carried out, dry chloroform is added, reaction is carried out for 24 hours at room temperature, and self-assembly driven by intermolecular hydrogen bond between barbituric acid units and the compound A is utilized, thus obtaining the chiral porous stationary phase material.
Wherein, the structural general formula of the chiral porous stationary phase material is:
Wherein/> The polymerization degree m=5 to 100. The novel barbituric acid polyisonitrile with the polymerization degree can effectively control the pore diameter change of the supermolecule organic framework through the polymerization degree, and the pore diameter of the novel barbituric acid polyisonitrile is increased along with the increase of the polymerization degree.
Dynamic light scattering analysis and front and back nuclear magnetic hydrogen spectra were performed on the chiral separation porous stationary phase material in this example. The change of the particle size of the chiral porous stationary phase materials with different polymerization degrees further proves the influence of the different polymerization degrees on the chiral porous stationary phase materials, the particle size of the supermolecular organic framework is increased along with the increase of the polymerization degree, and the dynamic light scattering spectrum is shown in figure 5; the nuclear magnetic hydrogen spectrogram of the chiral porous stationary phase material assembled before and after is shown in figure 6.
Example 6
A chiral separation porous material and a synthesis method thereof comprise the following steps:
The compound A (20 mg) prepared in example 4 and the barbituric acid isonitrile polymer P2 (80 mg) prepared in example 3 with two ends are added into a polymerization bottle, under the anhydrous and anaerobic condition, vacuum pumping and nitrogen charging are carried out, dry chloroform is added, reaction is carried out for 24 hours at room temperature, and self-assembly driven by intermolecular hydrogen bond between barbituric acid units and the compound A is utilized, thus obtaining the chiral porous stationary phase material.
Wherein, the structural general formula of the chiral porous stationary phase material is:
Wherein/> The polymerization degree m=5 to 100. The novel barbituric acid polyisonitrile with the polymerization degree can effectively control the pore diameter change of the supermolecule organic framework through the polymerization degree, and the pore diameter of the novel barbituric acid polyisonitrile is increased along with the increase of the polymerization degree.
Example 7
A preparation method of a chiral column of a chiral separation porous material comprises the following steps:
The chiral separation porous stationary phase material chiral column was prepared by uniformly stirring amino silica (800 mg) and the chiral stationary phase material (200 mg) having a polymerization degree of 10 described in example 5 in a homogenization tank, pressurizing to 40MPa, and discharging all the gas out of the chiral column.
The racemate is split by using the prepared chiral separation porous stationary phase material chiral column in the embodiment, and the racemate is tested by liquid chromatography respectively, as shown in fig. 7, left diagram: naproxen methyl ester; ketoprofen methyl ester; phenethyl alcohol ethyl ester, right panel: phenethylamine; benzoin; naproxen. The resolution of the racemate by chiral separation of the porous stationary phase material chiral column shows that the liquid spectrum is two peaks, namely the racemate is successfully split.
Example 8
A preparation method of a chiral column of a chiral separation porous material comprises the following steps:
The chiral separation porous stationary phase material chiral column was prepared by uniformly stirring amino silica (800 mg) and the chiral stationary phase material (200 mg) having a polymerization degree of 10 described in example 6 in a homogenization tank, pressurizing to 40MPa, and discharging all the gas out of the chiral column.
The foregoing is merely illustrative and explanatory of the invention, as various modifications and additions may be made to the particular embodiments described, or in a similar manner, by those skilled in the art, without departing from the structure of the invention or beyond the scope of the invention as defined in the appended claims.
Claims (10)
1. The palladium-alkyne barbiturate catalyst is characterized by comprising the following chemical structural formula:
2. A process for preparing a palladium barbiturate catalyst according to claim 1, wherein: the alkynyl barbituric acid derivative reacts with bis (triethylphosphine) palladium dichloride to obtain the barbituric acid palladium alkyne catalyst, wherein the structural general formula of the alkynyl barbituric acid derivative is as follows:
3. a preparation method of a phenylisonitrile polymer with barbituric acid at two ends is characterized by comprising the following steps: the palladium butoxide catalyst in claim 1 is used for carrying out active polymerization on a phenylisonitrile monomer, so as to obtain the phenylisonitrile polymer with barbituric acid at two ends.
4. A process for the preparation of a phenylisonitrile polymer having barbituric acid at both ends as defined in claim 3, wherein:
the active polymerization reaction is carried out in the anhydrous and anaerobic atmosphere with nitrogen, the reaction temperature is 50-90 ℃, and the reaction time is 6-24 h;
The solvent A is added during the active polymerization reaction, and the solvent A is one or more of tetrahydrofuran, chloroform and toluene;
The molar ratio of the palladium catalyst with the palladium alkyne barbiturate and the benzoisonitrile monomer at the two ends is 1: (5-100);
when the input amount of the phenylisonitrile monomer is 30-100 mg, the addition amount of the solvent A is 1-3 mL;
the phenyl isonitrile monomer Wherein the R substituent is an alkyl chain or an oxygen chain, the number of carbon in the alkyl chain is any number of 2-10, and the number of carbon and oxygen in the oxygen chain is any number of 2-10.
5. A phenylisonitrile polymer with barbituric acid at both ends prepared by the preparation method of a phenylisonitrile polymer with barbituric acid at both ends according to claim 3, wherein the phenylisonitrile polymer with barbituric acid at both ends has the chemical structural formula:
wherein R is alkyl chain or oxygen chain, the number of carbon in the alkyl chain is any number in 2-10, the number of carbon and oxygen in the oxygen chain is any number in 2-10, and the polymerization degree m=any number in 5-100.
6. A preparation method of a chiral separation porous stationary phase material is characterized by comprising the following steps: the method comprises the steps of adding a phenylisonitrile polymer with barbituric acid at two ends and a compound A into a reagent A for reaction, and obtaining the chiral porous stationary phase material by self-assembly driven by intermolecular hydrogen bonds between barbituric acid units and the compound A, wherein the reagent A is one or more of tetrahydrofuran, chloroform and toluene, and the structural formula of the compound A is as follows:
7. The method for preparing the chiral separation porous stationary phase material according to claim 6, wherein the method comprises the following steps:
the reaction is carried out in the atmosphere of anhydrous oxygen-free and nitrogen, the reaction temperature is room temperature, and the reaction time is 6-24 hours;
The molar ratio of the phenylisonitrile polymer with barbituric acid at two ends to the compound A is 3:1.
8. A chiral separation porous stationary phase material, characterized in that: the chiral separation porous stationary phase material is prepared by the preparation method of the chiral separation porous stationary phase material according to claim 6, and the chiral separation porous stationary phase material has the following structural general formula:
Wherein R substituent is alkyl chain or oxygen chain, the number of carbon in the alkyl chain is any number in 2-10, the number of carbon and oxygen in the oxygen chain is any number in 2-10, and the polymerization degree m is any number in 5-100.
9. A preparation method of a chiral column of a chiral separation porous material is characterized by comprising the following steps: uniformly stirring the filler and the chiral separation porous stationary phase material according to claim 8, and pressurizing to 40MPa to enable the filler and the chiral separation porous stationary phase material to discharge all gas out of the chiral column, thereby obtaining the chiral separation porous material chiral column.
10. The method for preparing the chiral column of the chiral separation porous material according to claim 9, which is characterized in that:
The filler is one or two of silicon dioxide and amino silicon dioxide;
The mass ratio of the filler to the chiral separation porous stationary phase material is 10:1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202410314138.2A CN118206589A (en) | 2024-03-19 | 2024-03-19 | Chiral separation porous material and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202410314138.2A CN118206589A (en) | 2024-03-19 | 2024-03-19 | Chiral separation porous material and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN118206589A true CN118206589A (en) | 2024-06-18 |
Family
ID=91445646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202410314138.2A Pending CN118206589A (en) | 2024-03-19 | 2024-03-19 | Chiral separation porous material and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN118206589A (en) |
-
2024
- 2024-03-19 CN CN202410314138.2A patent/CN118206589A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Murer et al. | Synthesis and properties of first and second generation chiral dendrimers with triply branched units: A spectacular case of diastereoselectivity | |
| CN118206589A (en) | Chiral separation porous material and preparation method thereof | |
| JP2000515910A (en) | Multi-arm star polymers with well-defined cores and methods for their synthesis | |
| CN104311582A (en) | Schiff base zinc compound, preparation method of schiff base zinc compound, and preparation method of polylactic acid | |
| EP1288201B1 (en) | Optically active maleimide derivatives, optically active polymaleimide derivatives, production method thereof, separating agent using the same derivative, and method for separating optically active compounds using the same agent | |
| CN108948349A (en) | A kind of spiro polymer material and preparation method thereof | |
| US7645889B2 (en) | Optically active polymaleimide derivatives and process for their production | |
| CN109251227B (en) | Chiral compound containing ferrocene skeleton and rigid spiro structure, synthesis and application | |
| CN114195787A (en) | 2-nitro-2-azaadamantane-4, 6, 8-triol trinitrate and preparation method thereof | |
| JP4534329B2 (en) | Separation agent comprising optically active polymaleimide derivative and method for separating optically active compound using the same | |
| CN111362962A (en) | Tetrafluorobenzyl norcantharidin carboxylate and synthesis method thereof | |
| CN108250241B (en) | N, N, N coordination trivalent dicyclic phosphide, synthesis method and catalytic application thereof | |
| CN113387886A (en) | 2-aminodibenzo [ c, e ] azepine compound and synthetic method thereof | |
| CN111253415A (en) | Norcantharidin carboxylic acid trifluorobenzyl ester and synthetic method and application thereof | |
| CN111978448B (en) | Ureido-modified (S) -2-ethynylpyrrolidine and preparation method and application thereof | |
| CN114213440B (en) | 2-boron alkenyl oxygen ether compound and preparation method thereof | |
| JP4380367B2 (en) | Optically active maleimide derivative, optically active polymaleimide derivative, production method thereof, separating agent comprising optically active polymaleimide derivative, and separation method of optically active compound using the same | |
| CN102260224A (en) | Method for synthesizing 2-morpholone derivatives | |
| JP2001106729A (en) | Optically active polymaleimide derivative, method for producing the same, optical resolution agent consisting of the same and method for resolution of optically active compound using the same | |
| CN117089048A (en) | Ordered supermolecule organic framework with uniform and adjustable aperture and preparation method thereof | |
| Chen et al. | Synthesis of Trimethylamine‐[14C] carboxyborane and Trimethylamine‐[14C] carboxymethoxyborane and L1210 Leukemia Cell Uptake | |
| CN115054599A (en) | Application of 2-aminoindole compounds in antitumor drugs | |
| CN111253414A (en) | Synthesis of perfluorobenzyl norcantharidinate carboxylate and anti-tumor application thereof | |
| CN118240194A (en) | Application of (thio) urea/phosphazene alkali mixture, polyester and preparation method thereof | |
| CN115819267A (en) | Etomidate intermediate product and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination |