PL154878B1 - Method of obtaining novel phosphorus containing derivatives of 3-hydroxybutanic acid - Google Patents

Info

Publication number

PL154878B1

PL154878B1 PL27259888A PL27259888A PL154878B1 PL 154878 B1 PL154878 B1 PL 154878B1 PL 27259888 A PL27259888 A PL 27259888A PL 27259888 A PL27259888 A PL 27259888A PL 154878 B1 PL154878 B1 PL 154878B1

Authority

PL

Poland

Prior art keywords

group

hydrogen

formula

alkyl

solution

Prior art date

1987-05-22

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims description 17
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims description 5
• 229910052698 phosphorus Inorganic materials 0.000 title claims description 5
• 239000011574 phosphorus Substances 0.000 title claims description 5
• WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical class CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 title 1
• 229910052739 hydrogen Inorganic materials 0.000 claims description 125
• 239000001257 hydrogen Substances 0.000 claims description 124
• 125000000217 alkyl group Chemical group 0.000 claims description 102
• 150000002431 hydrogen Chemical class 0.000 claims description 74
• -1 phenyl- Chemical group 0.000 claims description 66
• 239000002253 acid Substances 0.000 claims description 56
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
• 239000000460 chlorine Substances 0.000 claims description 51
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 45
• 150000003839 salts Chemical class 0.000 claims description 43
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 36
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 31
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 28
• 125000003545 alkoxy group Chemical group 0.000 claims description 28
• 229910052801 chlorine Inorganic materials 0.000 claims description 27
• 229910052736 halogen Inorganic materials 0.000 claims description 26
• 125000001153 fluoro group Chemical group F* 0.000 claims description 25
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 24
• 150000002367 halogens Chemical class 0.000 claims description 23
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
• 229960000583 acetic acid Drugs 0.000 claims description 19
• 230000015572 biosynthetic process Effects 0.000 claims description 19
• 150000002148 esters Chemical class 0.000 claims description 18
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 17
• 229910052731 fluorine Inorganic materials 0.000 claims description 17
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 16
• 239000011737 fluorine Substances 0.000 claims description 16
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
• 229910052794 bromium Inorganic materials 0.000 claims description 13
• 239000012362 glacial acetic acid Substances 0.000 claims description 13
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 10
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
• 239000001273 butane Substances 0.000 claims description 8
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
• 125000004429 atom Chemical group 0.000 claims description 5
• 125000005059 halophenyl group Chemical group 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 239000011593 sulfur Chemical group 0.000 claims description 5
• 150000001447 alkali salts Chemical class 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• 238000002360 preparation method Methods 0.000 claims description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• 230000009471 action Effects 0.000 claims description 3
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
• JUUYGPLMBNHCFZ-UHFFFAOYSA-N acetylene phosphane Chemical compound P.C#C JUUYGPLMBNHCFZ-UHFFFAOYSA-N 0.000 claims description 2
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
• 238000003776 cleavage reaction Methods 0.000 claims description 2
• ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 2
• 239000002515 guano Substances 0.000 claims description 2
• 230000007017 scission Effects 0.000 claims description 2
• KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 2
• KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims 2
• FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical compound O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-UHFFFAOYSA-N 0.000 claims 1
• 101150065749 Churc1 gene Proteins 0.000 claims 1
• 241000353790 Doru Species 0.000 claims 1
• 229930194542 Keto Natural products 0.000 claims 1
• 229910018540 Si C Inorganic materials 0.000 claims 1
• 229910003691 SiBr Inorganic materials 0.000 claims 1
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
• 239000002934 diuretic Substances 0.000 claims 1
• 230000001882 diuretic effect Effects 0.000 claims 1
• 125000001033 ether group Chemical group 0.000 claims 1
• 230000007062 hydrolysis Effects 0.000 claims 1
• 238000006460 hydrolysis reaction Methods 0.000 claims 1
• 150000002500 ions Chemical class 0.000 claims 1
• 125000000468 ketone group Chemical group 0.000 claims 1
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
• 229910010271 silicon carbide Inorganic materials 0.000 claims 1
• 239000000344 soap Substances 0.000 claims 1
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 236
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 235
• 239000000243 solution Substances 0.000 description 206
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 174
• 239000000203 mixture Substances 0.000 description 170
• 150000001875 compounds Chemical class 0.000 description 152
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 131
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 118
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 104
• 239000000741 silica gel Substances 0.000 description 100
• 229910002027 silica gel Inorganic materials 0.000 description 100
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 93
• 238000004809 thin layer chromatography Methods 0.000 description 84
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 75
• 239000011541 reaction mixture Substances 0.000 description 70
• 239000003921 oil Substances 0.000 description 67
• 235000019198 oils Nutrition 0.000 description 67
• 229910052786 argon Inorganic materials 0.000 description 66
• 239000007787 solid Substances 0.000 description 66
• 235000019439 ethyl acetate Nutrition 0.000 description 58
• 239000000284 extract Substances 0.000 description 49
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
• 239000012267 brine Substances 0.000 description 43
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 42
• 239000012043 crude product Substances 0.000 description 42
• 229920006395 saturated elastomer Polymers 0.000 description 42
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 42
• 239000000047 product Substances 0.000 description 41
• 238000007792 addition Methods 0.000 description 36
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 35
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
• 238000006243 chemical reaction Methods 0.000 description 32
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 29
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 27
• 150000004702 methyl esters Chemical class 0.000 description 26
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
• 239000010410 layer Substances 0.000 description 23
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
• 238000005481 NMR spectroscopy Methods 0.000 description 22
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 22
• 239000000499 gel Substances 0.000 description 22
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 21
• 238000004458 analytical method Methods 0.000 description 21
• 235000012000 cholesterol Nutrition 0.000 description 21
• 239000000706 filtrate Substances 0.000 description 21
• 238000001228 spectrum Methods 0.000 description 19
• 238000003756 stirring Methods 0.000 description 18
• 239000000725 suspension Substances 0.000 description 18
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 17
• 239000002904 solvent Substances 0.000 description 17
• 239000002244 precipitate Substances 0.000 description 16
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
• 239000012300 argon atmosphere Substances 0.000 description 15
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 15
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
• 125000001309 chloro group Chemical group Cl* 0.000 description 14
• ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 14
• 238000003818 flash chromatography Methods 0.000 description 14
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 14
• KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 13
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
• 229910052757 nitrogen Inorganic materials 0.000 description 12
• 102000004190 Enzymes Human genes 0.000 description 11
• 108090000790 Enzymes Proteins 0.000 description 11
• 229910052799 carbon Inorganic materials 0.000 description 11
• 239000002609 medium Substances 0.000 description 11
• 239000012074 organic phase Substances 0.000 description 11
• 239000011780 sodium chloride Substances 0.000 description 11
• 230000000694 effects Effects 0.000 description 10
• 238000000746 purification Methods 0.000 description 10
• 125000001424 substituent group Chemical group 0.000 description 10
• 238000003786 synthesis reaction Methods 0.000 description 10
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
• 125000003118 aryl group Chemical group 0.000 description 9
• 239000012298 atmosphere Substances 0.000 description 9
• 125000004432 carbon atom Chemical group C* 0.000 description 9
• 239000003795 chemical substances by application Substances 0.000 description 9
• 229940079593 drug Drugs 0.000 description 9
• 239000003814 drug Substances 0.000 description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
• 125000005843 halogen group Chemical group 0.000 description 9
• 239000012299 nitrogen atmosphere Substances 0.000 description 9
• 239000000523 sample Substances 0.000 description 9
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
• 102000004316 Oxidoreductases Human genes 0.000 description 8
• 108090000854 Oxidoreductases Proteins 0.000 description 8
• 241000700159 Rattus Species 0.000 description 8
• 239000008346 aqueous phase Substances 0.000 description 8
• 125000003710 aryl alkyl group Chemical group 0.000 description 8
• 238000001914 filtration Methods 0.000 description 8
• 239000003112 inhibitor Substances 0.000 description 8
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 7
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
• 150000001299 aldehydes Chemical class 0.000 description 7
• 239000012153 distilled water Substances 0.000 description 7
• 239000011521 glass Substances 0.000 description 7
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 7
• 239000005457 ice water Substances 0.000 description 7
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
• 235000019341 magnesium sulphate Nutrition 0.000 description 7
• 238000001819 mass spectrum Methods 0.000 description 7
• 239000012044 organic layer Substances 0.000 description 7
• 239000000377 silicon dioxide Substances 0.000 description 7
• 238000003307 slaughter Methods 0.000 description 7
• 239000011734 sodium Substances 0.000 description 7
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
• 239000000538 analytical sample Substances 0.000 description 6
• 210000004027 cell Anatomy 0.000 description 6
• 239000012259 ether extract Substances 0.000 description 6
• 210000003494 hepatocyte Anatomy 0.000 description 6
• 150000002596 lactones Chemical class 0.000 description 6
• 210000004185 liver Anatomy 0.000 description 6
• 238000002844 melting Methods 0.000 description 6
• 230000008018 melting Effects 0.000 description 6
• OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
• ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical group [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 6
• 235000017557 sodium bicarbonate Nutrition 0.000 description 6
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
• VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 5
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
• 239000000872 buffer Substances 0.000 description 5
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
• 235000011089 carbon dioxide Nutrition 0.000 description 5
• RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 5
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• 229910052744 lithium Inorganic materials 0.000 description 5
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• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
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• 239000011575 calcium Substances 0.000 description 4
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• 229910052804 chromium Inorganic materials 0.000 description 4
• 239000011651 chromium Substances 0.000 description 4
• 150000005690 diesters Chemical class 0.000 description 4
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
• 238000004821 distillation Methods 0.000 description 4
• 238000010828 elution Methods 0.000 description 4
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• 238000004108 freeze drying Methods 0.000 description 4
• 238000011534 incubation Methods 0.000 description 4
• 239000000543 intermediate Substances 0.000 description 4
• 239000011777 magnesium Substances 0.000 description 4
• QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
• 229910052753 mercury Inorganic materials 0.000 description 4
• 125000001624 naphthyl group Chemical group 0.000 description 4
• 239000010502 orange oil Substances 0.000 description 4
• 239000003960 organic solvent Substances 0.000 description 4
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
• 239000010452 phosphate Substances 0.000 description 4
• 102000004169 proteins and genes Human genes 0.000 description 4
• 108090000623 proteins and genes Proteins 0.000 description 4
• 238000012360 testing method Methods 0.000 description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
• QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical group COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 3
• WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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