JPH11106360A

JPH11106360A - アダマンタン誘導体及びその製造方法

アダマンタン誘導体及びその製造方法

Info

Publication number: JPH11106360A
Authority: JP; Japan
Prior art keywords: group; protected; compound; protecting; adamantanol
Prior art date: 1997-03-11
Legal status : Pending

Application number

JP10053921A

Other languages

English (en)

Japanese (ja)

Other versions

JPH11106360A5 (https=

Inventor

Tatsuya Nakano

達也中野

Yasutaka Ishii

康敬石井

Narihisa Hirai

成尚平井

Current Assignee

Daicel Corp

Original Assignee

Daicel Chemical Industries Ltd

Priority date

1997-03-11

Filing date

1998-03-05

Publication date

1999-04-20

1998-03-05 Application filed by Daicel Chemical Industries Ltd filed Critical Daicel Chemical Industries Ltd

1998-03-05 Priority to JP10053921A priority Critical patent/JPH11106360A/ja

1999-04-20 Publication of JPH11106360A publication Critical patent/JPH11106360A/ja

2008-03-06 Publication of JPH11106360A5 publication Critical patent/JPH11106360A5/ja

Status Pending legal-status Critical Current

Links

ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical class C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 title claims abstract description 171
238000004519 manufacturing process Methods 0.000 title claims description 18
-1 (protected) hydroxyl Chemical group 0.000 claims abstract description 268
150000001875 compounds Chemical class 0.000 claims abstract description 178
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 163
238000000034 method Methods 0.000 claims abstract description 100
229910052760 oxygen Inorganic materials 0.000 claims abstract description 96
239000001301 oxygen Substances 0.000 claims abstract description 94
238000007254 oxidation reaction Methods 0.000 claims abstract description 81
125000000217 alkyl group Chemical group 0.000 claims abstract description 60
239000003054 catalyst Substances 0.000 claims abstract description 58
230000003647 oxidation Effects 0.000 claims abstract description 50
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 49
238000006396 nitration reaction Methods 0.000 claims abstract description 47
238000006473 carboxylation reaction Methods 0.000 claims abstract description 26
150000003949 imides Chemical class 0.000 claims abstract description 13
230000021523 carboxylation Effects 0.000 claims abstract description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
125000006239 protecting group Chemical group 0.000 claims description 154
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 100
MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 93
125000003277 amino group Chemical group 0.000 claims description 76
125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 69
125000002252 acyl group Chemical group 0.000 claims description 56
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 55
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 50
125000001931 aliphatic group Chemical group 0.000 claims description 49
125000001424 substituent group Chemical group 0.000 claims description 35
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 33
239000002253 acid Substances 0.000 claims description 33
229910002091 carbon monoxide Inorganic materials 0.000 claims description 33
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 27
125000003545 alkoxy group Chemical group 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 26
125000003118 aryl group Chemical group 0.000 claims description 25
CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 claims description 24
125000004423 acyloxy group Chemical group 0.000 claims description 24
229910052757 nitrogen Inorganic materials 0.000 claims description 23
GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims description 21
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 15
239000003426 co-catalyst Substances 0.000 claims description 14
125000005843 halogen group Chemical group 0.000 claims description 14
230000000737 periodic effect Effects 0.000 claims description 14
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 11
239000007795 chemical reaction product Substances 0.000 claims description 10
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 7
MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 6
125000006574 non-aromatic ring group Chemical group 0.000 claims description 6
125000004430 oxygen atom Chemical group O* 0.000 claims description 6
125000004442 acylamino group Chemical group 0.000 claims description 5
239000001272 nitrous oxide Substances 0.000 claims description 5
229910052723 transition metal Inorganic materials 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
150000002430 hydrocarbons Chemical group 0.000 claims description 4
125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 3
229910021472 group 8 element Inorganic materials 0.000 claims description 3
230000001681 protective effect Effects 0.000 claims description 3
229910052727 yttrium Inorganic materials 0.000 claims description 3
BUXKULRFRATXSI-UHFFFAOYSA-N 1-hydroxypyrrole-2,5-dione Chemical compound ON1C(=O)C=CC1=O BUXKULRFRATXSI-UHFFFAOYSA-N 0.000 claims description 2
DBWVTDFTWIVIQA-UHFFFAOYSA-N 2-hydroxy-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione Chemical compound C1CCCC2C(=O)N(O)C(=O)C21 DBWVTDFTWIVIQA-UHFFFAOYSA-N 0.000 claims description 2
DPKHPTVBFHJMBL-UHFFFAOYSA-N 4,5,6,7-tetrabromo-2-hydroxyisoindole-1,3-dione Chemical compound BrC1=C(Br)C(Br)=C(Br)C2=C1C(=O)N(O)C2=O DPKHPTVBFHJMBL-UHFFFAOYSA-N 0.000 claims description 2
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 2
UTRBHXSKVVPTLY-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2-hydroxyisoindole-1,3-dione Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C2=C1C(=O)N(O)C2=O UTRBHXSKVVPTLY-UHFFFAOYSA-N 0.000 claims 1
125000000392 cycloalkenyl group Chemical group 0.000 claims 1
230000003287 optical effect Effects 0.000 abstract description 13
239000000463 material Substances 0.000 abstract description 11
QGQQCWHALQYFDK-UHFFFAOYSA-N n-(3-hydroxy-1-adamantyl)acetamide Chemical compound C1C(C2)CC3CC2(O)CC1(NC(=O)C)C3 QGQQCWHALQYFDK-UHFFFAOYSA-N 0.000 abstract description 8
229920000642 polymer Polymers 0.000 abstract description 4
239000011521 glass Substances 0.000 abstract description 3
239000013307 optical fiber Substances 0.000 abstract description 3
239000002994 raw material Substances 0.000 abstract description 3
239000011347 resin Substances 0.000 abstract description 3
229920005989 resin Polymers 0.000 abstract description 3
229910052736 halogen Inorganic materials 0.000 abstract description 2
150000002367 halogens Chemical class 0.000 abstract description 2
238000000576 coating method Methods 0.000 abstract 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 137
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 103
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 90
238000001819 mass spectrum Methods 0.000 description 57
MOLCWHCSXCKHAP-UHFFFAOYSA-N adamantane-1,3-diol Chemical compound C1C(C2)CC3CC1(O)CC2(O)C3 MOLCWHCSXCKHAP-UHFFFAOYSA-N 0.000 description 46
239000007788 liquid Substances 0.000 description 41
VLLNJDMHDJRNFK-UHFFFAOYSA-N adamantan-1-ol Chemical compound C1C(C2)CC3CC2CC1(O)C3 VLLNJDMHDJRNFK-UHFFFAOYSA-N 0.000 description 36
239000000758 substrate Substances 0.000 description 36
229960000583 acetic acid Drugs 0.000 description 35
235000011054 acetic acid Nutrition 0.000 description 34
239000007787 solid Substances 0.000 description 31
125000000524 functional group Chemical group 0.000 description 30
239000000203 mixture Substances 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
CJJMAWPEZKYJAP-UHFFFAOYSA-N 3-hydroxyadamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2(O)CC1(C(=O)O)C3 CJJMAWPEZKYJAP-UHFFFAOYSA-N 0.000 description 22
MCYBYTIPMYLHAK-UHFFFAOYSA-N adamantane-1,3,5-triol Chemical compound C1C(C2)CC3(O)CC1(O)CC2(O)C3 MCYBYTIPMYLHAK-UHFFFAOYSA-N 0.000 description 22
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
239000012634 fragment Substances 0.000 description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 19
239000012298 atmosphere Substances 0.000 description 16
125000004432 carbon atom Chemical group C* 0.000 description 16
239000007789 gas Substances 0.000 description 15
239000011572 manganese Substances 0.000 description 15
239000012299 nitrogen atmosphere Substances 0.000 description 15
238000006722 reduction reaction Methods 0.000 description 14
NOMFDAFFPMKYQB-UHFFFAOYSA-N 3-nitroadamantan-1-ol Chemical compound C1C(C2)CC3CC1(O)CC2([N+]([O-])=O)C3 NOMFDAFFPMKYQB-UHFFFAOYSA-N 0.000 description 13
JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 description 13
238000003756 stirring Methods 0.000 description 12
239000003638 chemical reducing agent Substances 0.000 description 11
MDTVSQIPVYZMKT-UHFFFAOYSA-N 3,5-dihydroxyadamantane-1-carboxylic acid Chemical compound C1C(C2)CC3(O)CC2(O)CC1(C(=O)O)C3 MDTVSQIPVYZMKT-UHFFFAOYSA-N 0.000 description 10
VLLCYTJNICRJJV-UHFFFAOYSA-N 5-nitroadamantane-1,3-diol Chemical compound C1C(C2)CC3(O)CC1(O)CC2([N+]([O-])=O)C3 VLLCYTJNICRJJV-UHFFFAOYSA-N 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000003795 chemical substances by application Substances 0.000 description 10
230000020169 heat generation Effects 0.000 description 10
239000003960 organic solvent Substances 0.000 description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 10
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
150000008065 acid anhydrides Chemical class 0.000 description 9
150000007513 acids Chemical class 0.000 description 9
PAVQGHWQOQZQEH-UHFFFAOYSA-N adamantane-1,3-dicarboxylic acid Chemical compound C1C(C2)CC3CC1(C(=O)O)CC2(C(O)=O)C3 PAVQGHWQOQZQEH-UHFFFAOYSA-N 0.000 description 9
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
239000011651 chromium Substances 0.000 description 9
150000002148 esters Chemical class 0.000 description 9
150000004820 halides Chemical class 0.000 description 9
150000008282 halocarbons Chemical class 0.000 description 9
150000004678 hydrides Chemical class 0.000 description 9
229910052751 metal Inorganic materials 0.000 description 9
PZGMISPWPRXBRZ-UHFFFAOYSA-N 5-hydroxyadamantane-1,3-dicarboxylic acid Chemical compound C1C(C2)CC3(O)CC1(C(=O)O)CC2(C(O)=O)C3 PZGMISPWPRXBRZ-UHFFFAOYSA-N 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 8
239000012346 acetyl chloride Substances 0.000 description 8
150000008064 anhydrides Chemical class 0.000 description 8
239000002585 base Substances 0.000 description 8
239000010949 copper Substances 0.000 description 8
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
239000002184 metal Substances 0.000 description 8
BEBYNYCNFDDIFE-UHFFFAOYSA-N methyl 3-hydroxyadamantane-1-carboxylate Chemical compound C1C(C2)CC3CC2(O)CC1(C(=O)OC)C3 BEBYNYCNFDDIFE-UHFFFAOYSA-N 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
239000010936 titanium Substances 0.000 description 8
HUJWKUYIFQXZEA-UHFFFAOYSA-N (3-hydroxy-1-adamantyl) acetate Chemical compound C1C(C2)CC3CC2(O)CC1(OC(=O)C)C3 HUJWKUYIFQXZEA-UHFFFAOYSA-N 0.000 description 7
BLHYUTKXIHHWLV-UHFFFAOYSA-N (3-nitro-1-adamantyl) acetate Chemical compound C1C(C2)CC3CC1(OC(=O)C)CC2([N+]([O-])=O)C3 BLHYUTKXIHHWLV-UHFFFAOYSA-N 0.000 description 7
HONLSNLUVRQMEK-UHFFFAOYSA-N 1-nitroadamantane Chemical compound C1C(C2)CC3CC2CC1([N+](=O)[O-])C3 HONLSNLUVRQMEK-UHFFFAOYSA-N 0.000 description 7
DWPIPTNBOVJYAD-UHFFFAOYSA-N 3-aminoadamantan-1-ol Chemical compound C1C(C2)CC3CC1(N)CC2(O)C3 DWPIPTNBOVJYAD-UHFFFAOYSA-N 0.000 description 7
IGSDAEDEJRBTEJ-UHFFFAOYSA-N adamantane-1,3,5-tricarboxylic acid Chemical compound C1C(C2)CC3(C(O)=O)CC1(C(=O)O)CC2(C(O)=O)C3 IGSDAEDEJRBTEJ-UHFFFAOYSA-N 0.000 description 7
150000007514 bases Chemical class 0.000 description 7
229940052761 dopaminergic adamantane derivative Drugs 0.000 description 7
229910052739 hydrogen Inorganic materials 0.000 description 7
229910052742 iron Inorganic materials 0.000 description 7
229910052748 manganese Inorganic materials 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
ZMLYIHMPXSWVDO-UHFFFAOYSA-N (3,5-dihydroxy-1-adamantyl) acetate Chemical compound C1C(C2)CC3(O)CC2(O)CC1(OC(=O)C)C3 ZMLYIHMPXSWVDO-UHFFFAOYSA-N 0.000 description 6
PFQLYOIUXIEHQE-UHFFFAOYSA-N (3-acetyloxy-1-adamantyl) acetate Chemical compound C1C(C2)CC3CC1(OC(=O)C)CC2(OC(C)=O)C3 PFQLYOIUXIEHQE-UHFFFAOYSA-N 0.000 description 6
USKZHFZEQOROEM-UHFFFAOYSA-N 1,3-dinitroadamantane Chemical compound C1C(C2)CC3CC1([N+](=O)[O-])CC2([N+]([O-])=O)C3 USKZHFZEQOROEM-UHFFFAOYSA-N 0.000 description 6
ZYLRDAOEBRPIGT-UHFFFAOYSA-N 1-adamantyl acetate Chemical compound C1C(C2)CC3CC2CC1(OC(=O)C)C3 ZYLRDAOEBRPIGT-UHFFFAOYSA-N 0.000 description 6
AKKMKUCYPBSEBN-UHFFFAOYSA-N 3,5-dinitroadamantan-1-ol Chemical compound C1C(C2)CC3([N+]([O-])=O)CC1(O)CC2([N+]([O-])=O)C3 AKKMKUCYPBSEBN-UHFFFAOYSA-N 0.000 description 6
FORAJDRXEYKDFJ-UHFFFAOYSA-N 3-(hydroxymethyl)adamantan-1-ol Chemical compound C1C(C2)CC3CC2(O)CC1(CO)C3 FORAJDRXEYKDFJ-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
IPRVKUPKUIJURA-UHFFFAOYSA-N adamantane-1,2,2-triol Chemical compound C1C(C2)CC3CC1C(O)(O)C2(O)C3 IPRVKUPKUIJURA-UHFFFAOYSA-N 0.000 description 6
125000002723 alicyclic group Chemical group 0.000 description 6
125000005907 alkyl ester group Chemical group 0.000 description 6
DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 6
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 6
238000009903 catalytic hydrogenation reaction Methods 0.000 description 6
238000007796 conventional method Methods 0.000 description 6
238000001816 cooling Methods 0.000 description 6
125000004185 ester group Chemical group 0.000 description 6
229910052750 molybdenum Inorganic materials 0.000 description 6
150000007524 organic acids Chemical class 0.000 description 6
229910052719 titanium Inorganic materials 0.000 description 6
229910052720 vanadium Inorganic materials 0.000 description 6
239000011701 zinc Substances 0.000 description 6
229910052726 zirconium Inorganic materials 0.000 description 6
ZFEOZOCXPIJZOQ-UHFFFAOYSA-N (3-acetyloxy-5-hydroxy-1-adamantyl) acetate Chemical compound C1C(C2)CC3(O)CC1(OC(=O)C)CC2(OC(C)=O)C3 ZFEOZOCXPIJZOQ-UHFFFAOYSA-N 0.000 description 5
YLWAGLKDWCUCKP-UHFFFAOYSA-N 5,7-dihydroxyadamantane-1,3-dicarboxylic acid Chemical compound C1C(C2)(O)CC3(O)CC1(C(=O)O)CC2(C(O)=O)C3 YLWAGLKDWCUCKP-UHFFFAOYSA-N 0.000 description 5
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
235000010338 boric acid Nutrition 0.000 description 5
229960002645 boric acid Drugs 0.000 description 5
150000001735 carboxylic acids Chemical class 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
229910052804 chromium Inorganic materials 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
229940093915 gynecological organic acid Drugs 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 5
229910052759 nickel Inorganic materials 0.000 description 5
229910017604 nitric acid Inorganic materials 0.000 description 5
235000005985 organic acids Nutrition 0.000 description 5
230000001590 oxidative effect Effects 0.000 description 5
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
229920005862 polyol Polymers 0.000 description 5
239000010948 rhodium Substances 0.000 description 5
239000011949 solid catalyst Substances 0.000 description 5
230000003595 spectral effect Effects 0.000 description 5
ZMZDLKCTDQXEDK-UHFFFAOYSA-N (3,5-diacetyloxy-1-adamantyl) acetate Chemical compound C1C(C2)CC3(OC(C)=O)CC1(OC(=O)C)CC2(OC(C)=O)C3 ZMZDLKCTDQXEDK-UHFFFAOYSA-N 0.000 description 4
QSISYLSFUBZMHR-UHFFFAOYSA-N (3-acetyloxy-5,7-dihydroxy-1-adamantyl) acetate Chemical compound C1C(C2)(O)CC3(O)CC1(OC(=O)C)CC2(OC(C)=O)C3 QSISYLSFUBZMHR-UHFFFAOYSA-N 0.000 description 4
CWYSSFRCRALTAK-UHFFFAOYSA-N 3-acetyloxyadamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC1(OC(=O)C)CC2(C(O)=O)C3 CWYSSFRCRALTAK-UHFFFAOYSA-N 0.000 description 4
YYXSKZYNOINBMR-UHFFFAOYSA-N 3-hydroxy-5-nitroadamantane-1-carboxylic acid Chemical compound C1C(C2)CC3(O)CC1(C(=O)O)CC2([N+]([O-])=O)C3 YYXSKZYNOINBMR-UHFFFAOYSA-N 0.000 description 4
AVDCKOPVXJIFKX-UHFFFAOYSA-N 3-hydroxy-n,n-dimethyladamantane-1-carboxamide Chemical compound C1C(C2)CC3CC2(O)CC1(C(=O)N(C)C)C3 AVDCKOPVXJIFKX-UHFFFAOYSA-N 0.000 description 4
OIMIOVIUFNKSAJ-UHFFFAOYSA-N 7-hydroxyadamantane-1,3,5-tricarboxylic acid Chemical compound C1C(C2)(O)CC3(C(O)=O)CC1(C(=O)O)CC2(C(O)=O)C3 OIMIOVIUFNKSAJ-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
229910052796 boron Inorganic materials 0.000 description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
229910052802 copper Inorganic materials 0.000 description 4
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 4
239000003446 ligand Substances 0.000 description 4
239000012280 lithium aluminium hydride Substances 0.000 description 4
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 4
239000010955 niobium Substances 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
229910052698 phosphorus Inorganic materials 0.000 description 4
239000000047 product Substances 0.000 description 4
235000019260 propionic acid Nutrition 0.000 description 4
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 4
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000000243 solution Substances 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
150000003623 transition metal compounds Chemical class 0.000 description 4
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 4
WDRIMDWXOMCUHD-UHFFFAOYSA-N (3,5,7-trihydroxy-1-adamantyl) acetate Chemical compound C1C(C2)(O)CC3(O)CC2(O)CC1(OC(=O)C)C3 WDRIMDWXOMCUHD-UHFFFAOYSA-N 0.000 description 3
YUIRYVZLYFHBCB-UHFFFAOYSA-N (3,5-dihydroxy-1-adamantyl) methyl carbonate Chemical compound C1C(C2)CC3(O)CC2(O)CC1(OC(=O)OC)C3 YUIRYVZLYFHBCB-UHFFFAOYSA-N 0.000 description 3
WXKUILQNQIMTGX-UHFFFAOYSA-N (3,5-dihydroxy-1-adamantyl) n-methylcarbamate Chemical compound C1C(C2)CC3(O)CC2(O)CC1(OC(=O)NC)C3 WXKUILQNQIMTGX-UHFFFAOYSA-N 0.000 description 3
ZZSWEEPJPCTZEI-UHFFFAOYSA-N (3-amino-1-adamantyl) acetate Chemical compound C1C(C2)CC3CC2(N)CC1(OC(=O)C)C3 ZZSWEEPJPCTZEI-UHFFFAOYSA-N 0.000 description 3
XKVCJIGKEAERDP-UHFFFAOYSA-N (3-hydroxy-1-adamantyl) methyl carbonate Chemical compound C1C(C2)CC3CC2(O)CC1(OC(=O)OC)C3 XKVCJIGKEAERDP-UHFFFAOYSA-N 0.000 description 3
IHLLSMFXPYWECL-UHFFFAOYSA-N (3-hydroxy-1-adamantyl) n-methylcarbamate Chemical compound C1C(C2)CC3CC2(O)CC1(OC(=O)NC)C3 IHLLSMFXPYWECL-UHFFFAOYSA-N 0.000 description 3
SHULVEMWIFDTAJ-UHFFFAOYSA-N (3-hydroxy-5-methoxycarbonyloxy-1-adamantyl) methyl carbonate Chemical compound C1C(C2)CC3(O)CC1(OC(=O)OC)CC2(OC(=O)OC)C3 SHULVEMWIFDTAJ-UHFFFAOYSA-N 0.000 description 3
YKZXYRKTAKVAKM-UHFFFAOYSA-N (3-isocyanato-1-adamantyl) acetate Chemical compound C1C(C2)CC3CC1(OC(=O)C)CC2(N=C=O)C3 YKZXYRKTAKVAKM-UHFFFAOYSA-N 0.000 description 3
ORFRPMZHXRQTCS-UHFFFAOYSA-N (3-methoxycarbonyloxy-1-adamantyl) acetate Chemical compound C1C(C2)CC3CC2(OC(C)=O)CC1(OC(=O)OC)C3 ORFRPMZHXRQTCS-UHFFFAOYSA-N 0.000 description 3
PAFQCJWCQJHEDS-UHFFFAOYSA-N (3-methoxycarbonyloxy-1-adamantyl) methyl carbonate Chemical compound C1C(C2)CC3CC1(OC(=O)OC)CC2(OC(=O)OC)C3 PAFQCJWCQJHEDS-UHFFFAOYSA-N 0.000 description 3
UOWGPUFYNXGPQX-UHFFFAOYSA-N (3-methoxycarbonyloxy-5-nitro-1-adamantyl) methyl carbonate Chemical compound C1C(C2)CC3(OC(=O)OC)CC1(OC(=O)OC)CC2([N+]([O-])=O)C3 UOWGPUFYNXGPQX-UHFFFAOYSA-N 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 3
LMYTYLMNPLNZLY-UHFFFAOYSA-N 3,5,7-trihydroxyadamantane-1-carboxylic acid Chemical compound C1C(C2)(O)CC3(O)CC2(O)CC1(C(=O)O)C3 LMYTYLMNPLNZLY-UHFFFAOYSA-N 0.000 description 3
AWLFXIYJMNYCRJ-UHFFFAOYSA-N 3,5-diaminoadamantan-1-ol Chemical compound C1C(C2)CC3(N)CC1(N)CC2(O)C3 AWLFXIYJMNYCRJ-UHFFFAOYSA-N 0.000 description 3
PHKMHGRDUDRDQB-UHFFFAOYSA-N 3-methoxycarbonyloxyadamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC1(OC(=O)OC)CC2(C(O)=O)C3 PHKMHGRDUDRDQB-UHFFFAOYSA-N 0.000 description 3
UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 3
UKTFPVMGUWUCRZ-UHFFFAOYSA-N 5,7-diaminoadamantane-1,3-diol Chemical compound C1C(C2)(N)CC3(O)CC1(N)CC2(O)C3 UKTFPVMGUWUCRZ-UHFFFAOYSA-N 0.000 description 3
UJNSVUMFPFEANP-UHFFFAOYSA-N 7-nitroadamantane-1,3,5-triol Chemical compound C1C(C2)(O)CC3(O)CC1(O)CC2([N+]([O-])=O)C3 UJNSVUMFPFEANP-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
229910052684 Cerium Inorganic materials 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
OGTMAUMOIWXPBP-UHFFFAOYSA-N [3-(dimethylcarbamoyl)-1-adamantyl] methyl carbonate Chemical compound C1C(C2)CC3CC1(OC(=O)OC)CC2(C(=O)N(C)C)C3 OGTMAUMOIWXPBP-UHFFFAOYSA-N 0.000 description 3
UEFXSYCSPYNGPS-UHFFFAOYSA-N [3-(hydroxymethyl)-1-adamantyl] acetate Chemical compound C1C(C2)CC3CC2(CO)CC1(OC(=O)C)C3 UEFXSYCSPYNGPS-UHFFFAOYSA-N 0.000 description 3
KHZROJKYUVLGIR-UHFFFAOYSA-N [3-(hydroxymethyl)-1-adamantyl] methyl carbonate Chemical compound C1C(C2)CC3CC2(CO)CC1(OC(=O)OC)C3 KHZROJKYUVLGIR-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
229910052782 aluminium Inorganic materials 0.000 description 3
238000007112 amidation reaction Methods 0.000 description 3
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 3
125000003710 aryl alkyl group Chemical group 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
239000004327 boric acid Substances 0.000 description 3
125000004744 butyloxycarbonyl group Chemical group 0.000 description 3
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
229940125904 compound 1 Drugs 0.000 description 3
229940125782 compound 2 Drugs 0.000 description 3
229940126214 compound 3 Drugs 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
RKQIZJNOBUJSTM-UHFFFAOYSA-N dimethyl 5-hydroxyadamantane-1,3-dicarboxylate Chemical compound C1C(C2)CC3(O)CC1(C(=O)OC)CC2(C(=O)OC)C3 RKQIZJNOBUJSTM-UHFFFAOYSA-N 0.000 description 3
YXMDGBXGJKYMQL-UHFFFAOYSA-N dimethyl adamantane-1,3-dicarboxylate Chemical compound C1C(C2)CC3CC1(C(=O)OC)CC2(C(=O)OC)C3 YXMDGBXGJKYMQL-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
230000008030 elimination Effects 0.000 description 3
238000003379 elimination reaction Methods 0.000 description 3
VVWVYPCOMWTLII-UHFFFAOYSA-N ethyl 3-hydroxyadamantane-1-carboxylate Chemical compound C1C(C2)CC3CC2(O)CC1(C(=O)OCC)C3 VVWVYPCOMWTLII-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
239000011261 inert gas Substances 0.000 description 3
125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 3
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 3
SRYHXPQPYWWEHZ-UHFFFAOYSA-N methyl (3-nitro-1-adamantyl) carbonate Chemical compound C1C(C2)CC3CC1(OC(=O)OC)CC2([N+]([O-])=O)C3 SRYHXPQPYWWEHZ-UHFFFAOYSA-N 0.000 description 3
ZVPMWMPHRIIXOO-UHFFFAOYSA-N methyl 3-methoxycarbonyloxyadamantane-1-carboxylate Chemical compound C1C(C2)CC3CC1(OC(=O)OC)CC2(C(=O)OC)C3 ZVPMWMPHRIIXOO-UHFFFAOYSA-N 0.000 description 3
MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 3
BCVXYGJCDZPKGV-UHFFFAOYSA-N n-(1-adamantyl)acetamide Chemical compound C1C(C2)CC3CC2CC1(NC(=O)C)C3 BCVXYGJCDZPKGV-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052758 niobium Inorganic materials 0.000 description 3
150000002828 nitro derivatives Chemical class 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
239000011574 phosphorus Substances 0.000 description 3
229910052697 platinum Inorganic materials 0.000 description 3
125000004742 propyloxycarbonyl group Chemical group 0.000 description 3
229910052703 rhodium Inorganic materials 0.000 description 3
229910052707 ruthenium Inorganic materials 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
150000004072 triols Chemical class 0.000 description 3
PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 3
229910052721 tungsten Inorganic materials 0.000 description 3
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
YQBXQBAKBLJMQS-UHFFFAOYSA-N (3,5-diacetyloxy-7-hydroxy-1-adamantyl) acetate Chemical compound C1C(C2)(O)CC3(OC(C)=O)CC1(OC(=O)C)CC2(OC(C)=O)C3 YQBXQBAKBLJMQS-UHFFFAOYSA-N 0.000 description 2
GTJJZUJGOSKXBL-UHFFFAOYSA-N (3-acetamido-1-adamantyl) acetate Chemical compound C1C(C2)CC3CC1(NC(=O)C)CC2(OC(C)=O)C3 GTJJZUJGOSKXBL-UHFFFAOYSA-N 0.000 description 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
JECAXWLZBJMQFG-UHFFFAOYSA-N 1,3,5-trinitroadamantane Chemical compound C1C(C2)CC3([N+]([O-])=O)CC1([N+](=O)[O-])CC2([N+]([O-])=O)C3 JECAXWLZBJMQFG-UHFFFAOYSA-N 0.000 description 2
PMMOCIUOCZCCNT-UHFFFAOYSA-N 3,5,7-trinitroadamantan-1-ol Chemical compound C1C(C2)([N+]([O-])=O)CC3([N+]([O-])=O)CC1(O)CC2([N+]([O-])=O)C3 PMMOCIUOCZCCNT-UHFFFAOYSA-N 0.000 description 2
WFFDVELKLYVNKM-UHFFFAOYSA-N 3,5-bis(dimethylamino)adamantan-1-ol Chemical compound C1C(C2)CC3(O)CC1(N(C)C)CC2(N(C)C)C3 WFFDVELKLYVNKM-UHFFFAOYSA-N 0.000 description 2
GAWYZBWUSRMXGH-UHFFFAOYSA-N 3,5-bis(methoxycarbonyloxy)adamantane-1-carboxylic acid Chemical compound C1C(C2)CC3(OC(=O)OC)CC1(OC(=O)OC)CC2(C(O)=O)C3 GAWYZBWUSRMXGH-UHFFFAOYSA-N 0.000 description 2
PJBDPRVLKHVTCY-UHFFFAOYSA-N 3-methyladamantan-1-ol Chemical compound C1C(C2)CC3CC1(C)CC2(O)C3 PJBDPRVLKHVTCY-UHFFFAOYSA-N 0.000 description 2
XKTXEVJPJZIGGL-UHFFFAOYSA-N 3-methyladamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC1(C)CC2(C(O)=O)C3 XKTXEVJPJZIGGL-UHFFFAOYSA-N 0.000 description 2
XDOJVRJZAGGBGC-UHFFFAOYSA-N 5,7-bis(diethylamino)adamantane-1,3-diol Chemical compound C1C(C2)(O)CC3(O)CC1(N(CC)CC)CC2(N(CC)CC)C3 XDOJVRJZAGGBGC-UHFFFAOYSA-N 0.000 description 2
IEZQYJOWXKPHOZ-UHFFFAOYSA-N 5,7-bis(ethylamino)adamantane-1,3-diol Chemical compound C1C(C2)(O)CC3(O)CC1(NCC)CC2(NCC)C3 IEZQYJOWXKPHOZ-UHFFFAOYSA-N 0.000 description 2
FVBABSGBJCRWQM-UHFFFAOYSA-N 5,7-dinitroadamantane-1,3-diol Chemical compound C1C(C2)(O)CC3([N+]([O-])=O)CC1(O)CC2([N+]([O-])=O)C3 FVBABSGBJCRWQM-UHFFFAOYSA-N 0.000 description 2
OTHKXWALZCWLGM-UHFFFAOYSA-N 5-aminoadamantane-1,3-diol Chemical compound C1C(C2)CC3(O)CC1(N)CC2(O)C3 OTHKXWALZCWLGM-UHFFFAOYSA-N 0.000 description 2
OJZXOFBHKPTMPZ-UHFFFAOYSA-N 5-methyladamantane-1,3-diol Chemical compound C1C(C2)CC3(O)CC1(C)CC2(O)C3 OJZXOFBHKPTMPZ-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
229910004373 HOAc Inorganic materials 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
229910052772 Samarium Inorganic materials 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
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QCBXLEMAQULYPC-UHFFFAOYSA-N [3,5-bis(methoxycarbonyloxy)-1-adamantyl] methyl carbonate Chemical compound C1C(C2)CC3(OC(=O)OC)CC1(OC(=O)OC)CC2(OC(=O)OC)C3 QCBXLEMAQULYPC-UHFFFAOYSA-N 0.000 description 2
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FOLJMFFBEKONJP-UHFFFAOYSA-N adamantane-1,3-diamine Chemical compound C1C(C2)CC3CC1(N)CC2(N)C3 FOLJMFFBEKONJP-UHFFFAOYSA-N 0.000 description 2
125000003158 alcohol group Chemical group 0.000 description 2
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150000008044 alkali metal hydroxides Chemical class 0.000 description 2
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
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VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
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150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
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238000002306 biochemical method Methods 0.000 description 2
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125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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125000005587 carbonate group Chemical group 0.000 description 2
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238000004440 column chromatography Methods 0.000 description 2
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150000001925 cycloalkenes Chemical group 0.000 description 2
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125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 2
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150000002009 diols Chemical class 0.000 description 2
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125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
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239000010931 gold Substances 0.000 description 2
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125000000623 heterocyclic group Chemical group 0.000 description 2
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230000003301 hydrolyzing effect Effects 0.000 description 2
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125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
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125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
229910052747 lanthanoid Inorganic materials 0.000 description 2
150000002602 lanthanoids Chemical class 0.000 description 2
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150000002697 manganese compounds Chemical class 0.000 description 2
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FRYUOUHISNWFTE-UHFFFAOYSA-L manganese(2+);dithiocyanate Chemical compound [Mn+2].[S-]C#N.[S-]C#N FRYUOUHISNWFTE-UHFFFAOYSA-L 0.000 description 2
238000004949 mass spectrometry Methods 0.000 description 2
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150000004706 metal oxides Chemical class 0.000 description 2
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AETJYAJVIPFQAB-UHFFFAOYSA-N methyl 3,5-dihydroxyadamantane-1-carboxylate Chemical compound C1C(C2)CC3(O)CC2(O)CC1(C(=O)OC)C3 AETJYAJVIPFQAB-UHFFFAOYSA-N 0.000 description 2
CLYOOVNORYNXMD-UHFFFAOYSA-N methyl adamantane-1-carboxylate Chemical compound C1C(C2)CC3CC2CC1(C(=O)OC)C3 CLYOOVNORYNXMD-UHFFFAOYSA-N 0.000 description 2
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
239000012046 mixed solvent Substances 0.000 description 2
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UFPOFGZJJBUSDT-UHFFFAOYSA-N n-(3,5,7-trihydroxy-1-adamantyl)acetamide Chemical compound C1C(C2)(O)CC3(O)CC2(O)CC1(NC(=O)C)C3 UFPOFGZJJBUSDT-UHFFFAOYSA-N 0.000 description 2
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SRCBKQQONBEGRD-UHFFFAOYSA-N n-(3-hydroxy-1-adamantyl)benzamide Chemical compound C1C(O)(C2)CC(C3)CC1CC32NC(=O)C1=CC=CC=C1 SRCBKQQONBEGRD-UHFFFAOYSA-N 0.000 description 2
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230000000802 nitrating effect Effects 0.000 description 2
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150000002826 nitrites Chemical class 0.000 description 2
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125000004433 nitrogen atom Chemical group N* 0.000 description 2
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150000002830 nitrogen compounds Chemical class 0.000 description 2
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229910052763 palladium Inorganic materials 0.000 description 2
239000000575 pesticide Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
235000021317 phosphate Nutrition 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000004576 sand Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
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229910052715 tantalum Inorganic materials 0.000 description 2
229910052713 technetium Inorganic materials 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
229910052718 tin Inorganic materials 0.000 description 2
239000011135 tin Substances 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
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MKFONEKGPYSCAF-UHFFFAOYSA-N (3,5-dihydroxy-7-methyl-1-adamantyl) acetate Chemical compound C1C(C2)(C)CC3(O)CC2(O)CC1(OC(=O)C)C3 MKFONEKGPYSCAF-UHFFFAOYSA-N 0.000 description 1
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WWHDHJVAIWFGIT-UHFFFAOYSA-N (3-acetamido-1-adamantyl) methyl carbonate Chemical compound C1C(C2)CC3CC2(NC(C)=O)CC1(OC(=O)OC)C3 WWHDHJVAIWFGIT-UHFFFAOYSA-N 0.000 description 1
SWSRQAZEOLNWDR-UHFFFAOYSA-N (3-acetyloxy-1-adamantyl)methyl acetate Chemical compound C1C(C2)CC3CC1(COC(=O)C)CC2(OC(C)=O)C3 SWSRQAZEOLNWDR-UHFFFAOYSA-N 0.000 description 1
VIRCZHPYUTVPDX-UHFFFAOYSA-N (3-acetyloxy-5-hydroxy-7-methyl-1-adamantyl) acetate Chemical compound C1C(C2)(C)CC3(O)CC1(OC(=O)C)CC2(OC(C)=O)C3 VIRCZHPYUTVPDX-UHFFFAOYSA-N 0.000 description 1
VCKLBNGKMBUZDB-UHFFFAOYSA-N (3-hydroxy-1-adamantyl)methyl methyl carbonate Chemical compound C1C(C2)CC3CC2(O)CC1(COC(=O)OC)C3 VCKLBNGKMBUZDB-UHFFFAOYSA-N 0.000 description 1
VQZWXYDJIMRGEU-UHFFFAOYSA-N (3-hydroxy-5-methyl-1-adamantyl) acetate Chemical compound C1C(C2)CC3(C)CC2(O)CC1(OC(=O)C)C3 VQZWXYDJIMRGEU-UHFFFAOYSA-N 0.000 description 1
DCRXMCMKHYJVTD-UHFFFAOYSA-N (3-methoxycarbonyloxy-1-adamantyl)methyl methyl carbonate Chemical compound C1C(C2)CC3CC1(COC(=O)OC)CC2(OC(=O)OC)C3 DCRXMCMKHYJVTD-UHFFFAOYSA-N 0.000 description 1
QNKMKDKGHALJFS-UHFFFAOYSA-N (3-methyl-1-adamantyl) acetate Chemical compound C1C(C2)CC3CC2(C)CC1(OC(=O)C)C3 QNKMKDKGHALJFS-UHFFFAOYSA-N 0.000 description 1
UNOVJFHOHFDGCP-UHFFFAOYSA-N (3-nitro-1-adamantyl) n-methylcarbamate Chemical compound C1C(C2)CC3CC1(OC(=O)NC)CC2([N+]([O-])=O)C3 UNOVJFHOHFDGCP-UHFFFAOYSA-N 0.000 description 1
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125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
OMAWWKIPXLIPDE-UHFFFAOYSA-N (ethyldiselanyl)ethane Chemical compound CC[Se][Se]CC OMAWWKIPXLIPDE-UHFFFAOYSA-N 0.000 description 1
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FUZZFPVZJGQAKD-UHFFFAOYSA-N 1,3-dimethyl-5-nitroadamantane Chemical compound C1C(C2)CC3(C)CC1(C)CC2([N+]([O-])=O)C3 FUZZFPVZJGQAKD-UHFFFAOYSA-N 0.000 description 1
CWNOIUTVJRWADX-UHFFFAOYSA-N 1,3-dimethyladamantane Chemical compound C1C(C2)CC3CC1(C)CC2(C)C3 CWNOIUTVJRWADX-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
QKAPBKHPGNCUQX-UHFFFAOYSA-N 1-adamantyl n-methylcarbamate Chemical compound C1C(C2)CC3CC2CC1(OC(=O)NC)C3 QKAPBKHPGNCUQX-UHFFFAOYSA-N 0.000 description 1
MDVGOOIANLZFCP-UHFFFAOYSA-N 1-adamantylmethanol Chemical compound C1C(C2)CC3CC2CC1(CO)C3 MDVGOOIANLZFCP-UHFFFAOYSA-N 0.000 description 1
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
AZCUIXHZJHFUFI-UHFFFAOYSA-N 1-butyladamantane Chemical compound C1C(C2)CC3CC2CC1(CCCC)C3 AZCUIXHZJHFUFI-UHFFFAOYSA-N 0.000 description 1
VBFWJRPNSXNARY-UHFFFAOYSA-N 1-ethoxy-4-(oxomethylidene)adamantan-2-one Chemical compound C1C(C2)CC3CC1(OCC)C(=O)C2C3=C=O VBFWJRPNSXNARY-UHFFFAOYSA-N 0.000 description 1
LDGYLGQNFGGRLQ-UHFFFAOYSA-N 1-ethoxyadamantane-2-carboxylic acid Chemical class C1C(C2)CC3CC2C(C(O)=O)C1(OCC)C3 LDGYLGQNFGGRLQ-UHFFFAOYSA-N 0.000 description 1
UZUCFTVAWGRMTQ-UHFFFAOYSA-N 1-methyladamantane Chemical compound C1C(C2)CC3CC2CC1(C)C3 UZUCFTVAWGRMTQ-UHFFFAOYSA-N 0.000 description 1
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
ISDSLPMQFWIUPU-UHFFFAOYSA-N 1-propan-2-yladamantane Chemical compound C1C(C2)CC3CC2CC1(C(C)C)C3 ISDSLPMQFWIUPU-UHFFFAOYSA-N 0.000 description 1
SCKYQTNMKBTHDQ-UHFFFAOYSA-N 1-propyladamantane Chemical compound C1C(C2)CC3CC2CC1(CCC)C3 SCKYQTNMKBTHDQ-UHFFFAOYSA-N 0.000 description 1
125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
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NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
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LVZQNGUHSFJVOM-UHFFFAOYSA-N 3,5,7-triacetyloxyadamantane-1-carboxylic acid Chemical compound C1C(C2)(OC(C)=O)CC3(OC(C)=O)CC1(OC(=O)C)CC2(C(O)=O)C3 LVZQNGUHSFJVOM-UHFFFAOYSA-N 0.000 description 1
BSBZKGYGFSUURU-UHFFFAOYSA-N 3,5,7-triaminoadamantan-1-ol Chemical compound C1C(C2)(N)CC3(N)CC1(N)CC2(O)C3 BSBZKGYGFSUURU-UHFFFAOYSA-N 0.000 description 1
DPTKJGGFVALCGQ-UHFFFAOYSA-N 3,5,7-tris(methylamino)adamantan-1-ol Chemical compound C1C(C2)(O)CC3(NC)CC1(NC)CC2(NC)C3 DPTKJGGFVALCGQ-UHFFFAOYSA-N 0.000 description 1
RTRRORPAGZPUFT-UHFFFAOYSA-N 3,5-bis(diethylamino)adamantan-1-ol Chemical compound C1C(C2)CC3(O)CC1(N(CC)CC)CC2(N(CC)CC)C3 RTRRORPAGZPUFT-UHFFFAOYSA-N 0.000 description 1
FHIHVIADHXSIEI-UHFFFAOYSA-N 3,5-bis(ethylamino)adamantan-1-ol Chemical compound C1C(C2)CC3(O)CC1(NCC)CC2(NCC)C3 FHIHVIADHXSIEI-UHFFFAOYSA-N 0.000 description 1
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RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
150000008107 benzenesulfonic acids Chemical class 0.000 description 1
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125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
RXUBZLMIGSAPEJ-UHFFFAOYSA-N benzyl n-aminocarbamate Chemical compound NNC(=O)OCC1=CC=CC=C1 RXUBZLMIGSAPEJ-UHFFFAOYSA-N 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
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238000006664 bond formation reaction Methods 0.000 description 1
UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical compound [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 1
229910000085 borane Inorganic materials 0.000 description 1
BGECDVWSWDRFSP-UHFFFAOYSA-N borazine Chemical compound B1NBNBN1 BGECDVWSWDRFSP-UHFFFAOYSA-N 0.000 description 1
229910052810 boron oxide Inorganic materials 0.000 description 1
150000001642 boronic acid derivatives Chemical class 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
HBBRVEMMVUOSTL-UHFFFAOYSA-N butyl n-aminocarbamate Chemical compound CCCCOC(=O)NN HBBRVEMMVUOSTL-UHFFFAOYSA-N 0.000 description 1
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
229910052793 cadmium Inorganic materials 0.000 description 1
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000004517 catalytic hydrocracking Methods 0.000 description 1
GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
229940011182 cobalt acetate Drugs 0.000 description 1
UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 1
229910001981 cobalt nitrate Inorganic materials 0.000 description 1
229910000361 cobalt sulfate Inorganic materials 0.000 description 1
229940044175 cobalt sulfate Drugs 0.000 description 1
KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
KYYSIVCCYWZZLR-UHFFFAOYSA-N cobalt(2+);dioxido(dioxo)molybdenum Chemical compound [Co+2].[O-][Mo]([O-])(=O)=O KYYSIVCCYWZZLR-UHFFFAOYSA-N 0.000 description 1
INDBQWVYFLTCFF-UHFFFAOYSA-L cobalt(2+);dithiocyanate Chemical compound [Co+2].[S-]C#N.[S-]C#N INDBQWVYFLTCFF-UHFFFAOYSA-L 0.000 description 1
AMFIJXSMYBKJQV-UHFFFAOYSA-L cobalt(2+);octadecanoate Chemical compound [Co+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AMFIJXSMYBKJQV-UHFFFAOYSA-L 0.000 description 1
TZWGXFOSKIHUPW-UHFFFAOYSA-L cobalt(2+);propanoate Chemical compound [Co+2].CCC([O-])=O.CCC([O-])=O TZWGXFOSKIHUPW-UHFFFAOYSA-L 0.000 description 1
QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
FCEOGYWNOSBEPV-FDGPNNRMSA-N cobalt;(z)-4-hydroxypent-3-en-2-one Chemical compound [Co].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FCEOGYWNOSBEPV-FDGPNNRMSA-N 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical class [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000000 cycloalkoxy group Chemical group 0.000 description 1
125000006254 cycloalkyl carbonyl group Chemical group 0.000 description 1
SMEJCQZFRMVYGC-UHFFFAOYSA-N cyclohexane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)C(C(O)=O)C1C(O)=O SMEJCQZFRMVYGC-UHFFFAOYSA-N 0.000 description 1
125000006639 cyclohexyl carbonyl group Chemical group 0.000 description 1
125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
LCGVCXIFXLGLHG-UHFFFAOYSA-N cyclopenta-1,3-diene;manganese(2+) Chemical compound [Mn+2].C1C=CC=[C-]1.C1C=CC=[C-]1 LCGVCXIFXLGLHG-UHFFFAOYSA-N 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
230000009849 deactivation Effects 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
238000003795 desorption Methods 0.000 description 1
JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
SSUJWGNUQPXQEH-UHFFFAOYSA-N diethyl 5-hydroxyadamantane-1,3-dicarboxylate Chemical compound C1C(C2)CC3(O)CC1(C(=O)OCC)CC2(C(=O)OCC)C3 SSUJWGNUQPXQEH-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
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CRLHSBRULQUYOK-UHFFFAOYSA-N dioxido(dioxo)tungsten;manganese(2+) Chemical compound [Mn+2].[O-][W]([O-])(=O)=O CRLHSBRULQUYOK-UHFFFAOYSA-N 0.000 description 1
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
229910001882 dioxygen Inorganic materials 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
AIGRXSNSLVJMEA-FQEVSTJZSA-N ethoxy-(4-nitrophenoxy)-phenyl-sulfanylidene-$l^{5}-phosphane Chemical compound O([P@@](=S)(OCC)C=1C=CC=CC=1)C1=CC=C([N+]([O-])=O)C=C1 AIGRXSNSLVJMEA-FQEVSTJZSA-N 0.000 description 1
VJNURTOPPQYNKY-UHFFFAOYSA-N ethyl 3,5-dihydroxy-7-methyladamantane-1-carboxylate Chemical compound C1C(C2)(C)CC3(O)CC2(O)CC1(C(=O)OCC)C3 VJNURTOPPQYNKY-UHFFFAOYSA-N 0.000 description 1
SYEXGNJRYPOUSI-UHFFFAOYSA-N ethyl adamantane-1-carboxylate Chemical compound C1C(C2)CC3CC2CC1(C(=O)OCC)C3 SYEXGNJRYPOUSI-UHFFFAOYSA-N 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
RAQDACVRFCEPDA-UHFFFAOYSA-L ferrous carbonate Chemical compound [Fe+2].[O-]C([O-])=O RAQDACVRFCEPDA-UHFFFAOYSA-L 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
150000002222 fluorine compounds Chemical class 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
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 description 1
229910052732 germanium Inorganic materials 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
229910052735 hafnium Inorganic materials 0.000 description 1
VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
MUTGBJKUEZFXGO-UHFFFAOYSA-N hexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21 MUTGBJKUEZFXGO-UHFFFAOYSA-N 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
CPSYWNLKRDURMG-UHFFFAOYSA-L hydron;manganese(2+);phosphate Chemical compound [Mn+2].OP([O-])([O-])=O CPSYWNLKRDURMG-UHFFFAOYSA-L 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
238000006358 imidation reaction Methods 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
229910000398 iron phosphate Inorganic materials 0.000 description 1
229910000358 iron sulfate Inorganic materials 0.000 description 1
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
DXTCFKRAUYBHRC-UHFFFAOYSA-L iron(2+);dithiocyanate Chemical compound [Fe+2].[S-]C#N.[S-]C#N DXTCFKRAUYBHRC-UHFFFAOYSA-L 0.000 description 1
UETZVSHORCDDTH-UHFFFAOYSA-N iron(2+);hexacyanide Chemical compound [Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] UETZVSHORCDDTH-UHFFFAOYSA-N 0.000 description 1
WBJZTOZJJYAKHQ-UHFFFAOYSA-K iron(3+) phosphate Chemical compound [Fe+3].[O-]P([O-])([O-])=O WBJZTOZJJYAKHQ-UHFFFAOYSA-K 0.000 description 1
LHOWRPZTCLUDOI-UHFFFAOYSA-K iron(3+);triperchlorate Chemical compound [Fe+3].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O LHOWRPZTCLUDOI-UHFFFAOYSA-K 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910052746 lanthanum Inorganic materials 0.000 description 1
FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
238000011068 loading method Methods 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
229940099596 manganese sulfate Drugs 0.000 description 1
239000011702 manganese sulphate Substances 0.000 description 1
235000007079 manganese sulphate Nutrition 0.000 description 1
MIVBAHRSNUNMPP-UHFFFAOYSA-N manganese(2+);dinitrate Chemical compound [Mn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MIVBAHRSNUNMPP-UHFFFAOYSA-N 0.000 description 1
SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 1
SZINCDDYCOIOJQ-UHFFFAOYSA-L manganese(2+);octadecanoate Chemical compound [Mn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O SZINCDDYCOIOJQ-UHFFFAOYSA-L 0.000 description 1
SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
XMWCXZJXESXBBY-UHFFFAOYSA-L manganese(ii) carbonate Chemical compound [Mn+2].[O-]C([O-])=O XMWCXZJXESXBBY-UHFFFAOYSA-L 0.000 description 1
NNYHMCFMPHPHOQ-UHFFFAOYSA-N mellitic anhydride Chemical compound O=C1OC(=O)C2=C1C(C(OC1=O)=O)=C1C1=C2C(=O)OC1=O NNYHMCFMPHPHOQ-UHFFFAOYSA-N 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
MLSKXPOBNQFGHW-UHFFFAOYSA-N methoxy(dioxido)borane Chemical compound COB([O-])[O-] MLSKXPOBNQFGHW-UHFFFAOYSA-N 0.000 description 1
BRDMIBYXNBJXML-UHFFFAOYSA-N methyl 3,5-dihydroxy-7-methyladamantane-1-carboxylate Chemical compound C1C(C2)(C)CC3(O)CC2(O)CC1(C(=O)OC)C3 BRDMIBYXNBJXML-UHFFFAOYSA-N 0.000 description 1
REGQUSRBYMNHSV-UHFFFAOYSA-N methyl 3-(dimethylcarbamoyl)adamantane-1-carboxylate Chemical compound C1C(C2)CC3CC1(C(=O)OC)CC2(C(=O)N(C)C)C3 REGQUSRBYMNHSV-UHFFFAOYSA-N 0.000 description 1
PHRXILUHVZPROT-UHFFFAOYSA-N methyl 3-acetyloxyadamantane-1-carboxylate Chemical compound C1C(C2)CC3CC2(OC(C)=O)CC1(C(=O)OC)C3 PHRXILUHVZPROT-UHFFFAOYSA-N 0.000 description 1
CUTDKNNJQATYEQ-UHFFFAOYSA-N methyl 3-hydroxy-5,7-dimethyladamantane-1-carboxylate Chemical compound C1C(C2)(C)CC3(C)CC2(O)CC1(C(=O)OC)C3 CUTDKNNJQATYEQ-UHFFFAOYSA-N 0.000 description 1
DSFOGFZTRHNMSD-UHFFFAOYSA-N methyl 3-hydroxy-5-methyladamantane-1-carboxylate Chemical compound C1C(C2)CC3(C)CC2(O)CC1(C(=O)OC)C3 DSFOGFZTRHNMSD-UHFFFAOYSA-N 0.000 description 1
DTCBBYZKUSZVIM-UHFFFAOYSA-N methyl [3-(methylcarbamoyloxy)-1-adamantyl] carbonate Chemical compound C1C(C2)CC3CC1(OC(=O)NC)CC2(OC(=O)OC)C3 DTCBBYZKUSZVIM-UHFFFAOYSA-N 0.000 description 1
229940095102 methyl benzoate Drugs 0.000 description 1
229940017219 methyl propionate Drugs 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000005078 molybdenum compound Substances 0.000 description 1
150000002752 molybdenum compounds Chemical class 0.000 description 1
VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
IMVYIPBEKGBLGO-UHFFFAOYSA-N n-(3,5,7-trihydroxy-1-adamantyl)benzamide Chemical compound C1C(O)(C2)CC(C3)(O)CC1(O)CC23NC(=O)C1=CC=CC=C1 IMVYIPBEKGBLGO-UHFFFAOYSA-N 0.000 description 1
VFFPWHLZSJNGNN-UHFFFAOYSA-N n-(3,5-diacetamido-7-hydroxy-1-adamantyl)acetamide Chemical compound C1C(C2)(O)CC3(NC(C)=O)CC1(NC(=O)C)CC2(NC(C)=O)C3 VFFPWHLZSJNGNN-UHFFFAOYSA-N 0.000 description 1
GLUBCNDYFRJVPU-UHFFFAOYSA-N n-(3-acetamido-5,7-dihydroxy-1-adamantyl)acetamide Chemical compound C1C(C2)(O)CC3(O)CC1(NC(=O)C)CC2(NC(C)=O)C3 GLUBCNDYFRJVPU-UHFFFAOYSA-N 0.000 description 1
UVYKMNUSWIMFSQ-UHFFFAOYSA-N n-(3-acetamido-5-hydroxy-1-adamantyl)acetamide Chemical compound C1C(C2)CC3(O)CC1(NC(=O)C)CC2(NC(C)=O)C3 UVYKMNUSWIMFSQ-UHFFFAOYSA-N 0.000 description 1
NWCXRBTUFUDSMI-UHFFFAOYSA-N n-(3-hydroxy-5-methyl-1-adamantyl)acetamide Chemical compound C1C(C2)CC3(C)CC2(O)CC1(NC(=O)C)C3 NWCXRBTUFUDSMI-UHFFFAOYSA-N 0.000 description 1
KVCLXTXHRCBPMP-UHFFFAOYSA-N n-(3-hydroxy-5-nitro-1-adamantyl)acetamide Chemical compound C1C(C2)CC3(O)CC1(NC(=O)C)CC2([N+]([O-])=O)C3 KVCLXTXHRCBPMP-UHFFFAOYSA-N 0.000 description 1
DNADEDKIQXROFJ-UHFFFAOYSA-N n-(4-oxo-1-adamantyl)acetamide Chemical compound C1C(C2)CC3CC1(NC(=O)C)CC2C3=O DNADEDKIQXROFJ-UHFFFAOYSA-N 0.000 description 1
125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
HKFZDVPCCOOGEV-UHFFFAOYSA-N nickel(3+);borate Chemical compound [Ni+3].[O-]B([O-])[O-] HKFZDVPCCOOGEV-UHFFFAOYSA-N 0.000 description 1
KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
LFLZOWIFJOBEPN-UHFFFAOYSA-N nitrate, nitrate Chemical compound O[N+]([O-])=O.O[N+]([O-])=O LFLZOWIFJOBEPN-UHFFFAOYSA-N 0.000 description 1
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
JFNLZVQOOSMTJK-UHFFFAOYSA-N norbornene Chemical group C1C2CCC1C=C2 JFNLZVQOOSMTJK-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
WIWVNQBYNTWQOW-UHFFFAOYSA-L oxovanadium(2+);diacetate Chemical compound [V+2]=O.CC([O-])=O.CC([O-])=O WIWVNQBYNTWQOW-UHFFFAOYSA-L 0.000 description 1
DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
229940049953 phenylacetate Drugs 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920002492 poly(sulfone) Polymers 0.000 description 1
229920002312 polyamide-imide Polymers 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920001721 polyimide Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229910052702 rhenium Inorganic materials 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
150000003317 samarium compounds Chemical class 0.000 description 1
150000004671 saturated fatty acids Chemical class 0.000 description 1
229910052706 scandium Inorganic materials 0.000 description 1
SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
229910052711 selenium Inorganic materials 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 1
229910000367 silver sulfate Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
150000004763 sulfides Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 description 1
229910052714 tellurium Inorganic materials 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
150000003609 titanium compounds Chemical class 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
NFMWFGXCDDYTEG-UHFFFAOYSA-N trimagnesium;diborate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]B([O-])[O-].[O-]B([O-])[O-] NFMWFGXCDDYTEG-UHFFFAOYSA-N 0.000 description 1
SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
WQEVDHBJGNOKKO-UHFFFAOYSA-K vanadic acid Chemical compound O[V](O)(O)=O WQEVDHBJGNOKKO-UHFFFAOYSA-K 0.000 description 1
150000003682 vanadium compounds Chemical class 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
239000010457 zeolite Substances 0.000 description 1