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【结 构 式】 
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【分子编号】16259 【品名】(2S)oxiranylmethyl 3-nitrobenzenesulfonate; (S)-(+)-Glycidyl nosylate 【CA登记号】115314-14-2 |
【 分 子 式 】C9H9NO6S 【 分 子 量 】259.2396 【元素组成】C 41.7% H 3.5% N 5.4% O 37.03% S 12.37% |
合成路线1
该中间体在本合成路线中的序号：(XXII)4) The condensation of the chiral piperazine (VII) with (S)-(+)-glycicyl 3-nitrobenzenesulfonate (XXII) by means of diisopropylethylamine in DMF [or with (S)-glycidol (XXIII), tosyl chloride and NaH] gives the epoxide (XXIV), which is condensed with the propionamide (IV) by means of butyllithium in THF, yielding the protected hydroxyamide (XXV). The deprotection of (XXV) with aqueous HCl affords the dihydroxy-diamide (VIII), already obtained, which is finally alkylated with 3-(chloromethyl)pyridine (IX) as before.
| 【1】 Mealy, N.; Castaner, J.; Indinavir Sulfate. Drugs Fut 1996, 21, 6, 600. |
| 【2】 Askin, D.; Reider, P.; Rossen, K.; Varsolona, R.J.; Wells, K.M. (Merck & Co., Inc.); Process for making HIV protease inhibitors. WO 9502583 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 16241 | 1-[(3aS,8aR)-2,2-dimethyl-8,8a-dihydro-2H-indeno[1,2-d][1,3]oxazol-3(3aH)-yl]-3-phenyl-1-propanone | C21H23NO2 | 详情 | 详情 | |
| (VII) | 16244 | tert-butyl (3S)-3-[(tert-butylamino)carbonyl]tetrahydro-1(2H)-pyrazinecarboxylate | 150323-35-6 | C14H27N3O3 | 详情 | 详情 |
| (VIII) | 16245 | (2S)-1-((2S,4R)-4-benzyl-2-hydroxy-5-[[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino]-5-oxopentyl)-N-(tert-butyl)-2-piperazinecarboxamide | C30H42N4O4 | 详情 | 详情 | |
| (IX) | 15793 | 3-(Chloromethyl)pyridine | 3099-31-8 | C6H6ClN | 详情 | 详情 |
| (XXII) | 16259 | (2S)oxiranylmethyl 3-nitrobenzenesulfonate; (S)-(+)-Glycidyl nosylate | 115314-14-2 | C9H9NO6S | 详情 | 详情 |
| (XXIII) | 16260 | (R)-(+)-Glycidol; (2R)-Oxiranemethanol; (2R)oxiranylmethanol | 57044-25-4 | C3H6O2 | 详情 | 详情 |
| (XXIV) | 16261 | tert-butyl (3S)-3-[(tert-butylamino)carbonyl]-4-[(2R)oxiranylmethyl]tetrahydro-1(2H)-pyrazinecarboxylate | C17H31N3O4 | 详情 | 详情 | |
| (XXV) | 16262 | tert-butyl (3S)-4-[(2S,4R)-5-[(3aS,8aR)-2,2-dimethyl-8,8a-dihydro-2H-indeno[1,2-d][1,3]oxazol-3(3aH)-yl]-4-benzyl-2-hydroxy-5-oxopentyl]-3-[(tert-butylamino)carbonyl]-1-piperazinecarboxylate | C38H54N4O6 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VIII)In this scheme various methods are shown for the synthesis of (S)-atenolol: 1. Treatment of (R)-glycidyl 4-nitrobenzenesulfonate (I) with HCl (either concentrated or with dichloromethane) provides 3-chloropropyl derivative (II), which is then coupled with isopropylamine (III) in dichloromethane to afford 3-chloropropylisopropylamine (IV). Finally, condensation of (IV) with 2-(4-hydroxyphenyl)acetamide (V) by means of KOH in MeOH gives the desired product. Alternatively, derivative (IV) can be converted into (S)-atenolol by its condensation with 2-(4-hydroxy-phenyl)acetonitrile (VI) by means of KOH to yield compound (VII), followed by hydrolysis with HCl at 40 C. 2. Condensation of (R)-glycidyl 3-nitrobenzenesulfonate (VIII) with isopropylamine (III) followed by coupling with acetamide (V) by means of potassium tert-butylate in DMSO provides the desired product. 3. Treatment of (VIII) with HCl affords 2(S)-hydroxy-3-chloropropyl-3-nitrobenzenesulfonate (IX), which is first coupled with isopropylamine (III) to give (IV) and finally condensed with amide (V). 4. Coupling of chloro derivative (IX) with benzyl-protected isopropylamine (X) provides protected derivative (XI), which is then condensed with acetamide (V) by means of KOH in MeOH to give (XII). Finally, compound (XII) is hydrogenated over Pd/C in MeOH for removal of the benzyl group.
| 【1】 Westfelt, A.; Andersson, L.; Birgersson, B.; Westfelt, L.; Process for preparing homochiral amines and process for preparing intermediates for the preparation thereof, and the intermediates prepared in accordance with this process. WO 9110642 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 45631 | (2S)oxiranylmethyl 4-nitrobenzenesulfonate | C9H9NO6S | 详情 | 详情 | |
| (II) | 51089 | (2S)-3-chloro-2-hydroxypropyl 4-nitrobenzenesulfonate | C9H10ClNO6S | 详情 | 详情 | |
| (III) | 23933 | 2-Propanamine; Isopropylamine | 75-31-0 | C3H9N | 详情 | 详情 |
| (IV) | 51090 | (2S)-1-chloro-3-(isopropylamino)-2-propanol | C6H14ClNO | 详情 | 详情 | |
| (V) | 32754 | p-Hydroxyphenylacetamide; 2-(4-hydroxyphenyl)acetamide; 4-Hydroxybenzeneacetamide; 4-Hydroxyphenylacetamide | 17194-82-0 | C8H9NO2 | 详情 | 详情 |
| (VI) | 32753 | 2-(4-hydroxyphenyl)acetonitrile; 4-Hydroxybenzyl cyanide | 14191-95-8 | C8H7NO | 详情 | 详情 |
| (VII) | 51088 | 2-(4-[[(2S)-2-hydroxy-3-(isopropylamino)propyl]oxy]phenyl)acetonitrile | C14H20N2O2 | 详情 | 详情 | |
| (VIII) | 16259 | (2S)oxiranylmethyl 3-nitrobenzenesulfonate; (S)-(+)-Glycidyl nosylate | 115314-14-2 | C9H9NO6S | 详情 | 详情 |
| (IX) | 51091 | (2S)-3-chloro-2-hydroxypropyl 3-nitrobenzenesulfonate | C9H10ClNO6S | 详情 | 详情 | |
| (X) | 39750 | N-benzyl-N-isopropylamine; N-benzyl-2-propanamine | 102-97-6 | C10H15N | 详情 | 详情 |
| (XI) | 51092 | (2S)-1-[benzyl(isopropyl)amino]-3-chloro-2-propanol | C13H20ClNO | 详情 | 详情 | |
| (XII) | 51093 | 2-[4-([(2S)-3-[benzyl(isopropyl)amino]-2-hydroxypropyl]oxy)phenyl]acetamide | C21H28N2O3 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(IV)1) 4-(Benzyloxy)phenol (I) was protected as the silyl ether (II) by treatment with tert-butyldimethylsilyl chloride (TBDMS-Cl) in the presence of imidazole in DMF. Then, the benzyl group of (II) was removed by hydrogenolysis on Pd(OH)2/C to give 4-(tert-butyldimethylsilyloxy)phenol (III). This phenol was treated with NaH in DMF, and the resulting sodium phenoxide was alkylated with (S)-glycidyl 3-nitrobenzenesulfonate (IV) to provide epoxide (V) (1,2). Subsequent reaction of (V) with 4-aminophenethyl amine (VI) in refluxing MeOH gave the chiral phenoxypropanolamine (VII). Selective protection of the resultant secondary aliphatic amine with one equivalent of di-tert-butyl dicarbonate in THF afforded carbamate (VIII). Then, acylation of the aniline N atom with 4-bromobenzenesulfonyl chloride (IX) in the presence of pyridine gave sulfonamide (X). Finally, removal of both silyl ether and tert-butyl carbamate protecting groups using methanolic HCl provided the desired product.
| 【1】 Weber, A.E.; Mathvink, R.J.; Perkins, L.; Hutchins, J.E.; Candelore, M.R.; Tota, L.; Strader, C.D.; Wyvratt, M.J.; Fisher, M.H.; Potent, selective benzenesulfonamide agonists of the human beta3 adrenergic receptor. Bioorg Med Chem Lett 1998, 8, 9, 1101. |
| 【2】 Fisher, M.H.; Mathvink, R.J.; Ok, H.O.; Parmee, E.R.; Weber, A.E. (Merck & Co., Inc.); Substd. phenyl sulfonamides as selective beta3 agonists for the treatment of diabetes and obesity. CA 2114712; EP 0611003; JP 1995010827; US 5451677; WO 9418161 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 18956 | 4-(Benzyloxy)phenol; 4-Benzyloxyphenol | 103-16-2 | C13H12O2 | 详情 | 详情 |
| (II) | 18957 | [4-(benzyloxy)phenoxy](tert-butyl)dimethylsilane; benzyl 4-[[tert-butyl(dimethyl)silyl]oxy]phenyl ether | C19H26O2Si | 详情 | 详情 | |
| (III) | 18958 | 4-[[tert-butyl(dimethyl)silyl]oxy]phenol | C12H20O2Si | 详情 | 详情 | |
| (IV) | 16259 | (2S)oxiranylmethyl 3-nitrobenzenesulfonate; (S)-(+)-Glycidyl nosylate | 115314-14-2 | C9H9NO6S | 详情 | 详情 |
| (V) | 18960 | tert-butyl(dimethyl)[4-[(2S)oxiranylmethoxy]phenoxy]silane; tert-butyl(dimethyl)silyl 4-[(2S)oxiranylmethoxy]phenyl ether | C15H24O3Si | 详情 | 详情 | |
| (VI) | 18961 | 4-(2-aminoethyl)aniline; 4-(2-aminoethyl)phenylamine | 13472-00-9 | C8H12N2 | 详情 | 详情 |
| (VII) | 18962 | (2S)-1-[(4-aminophenethyl)amino]-3-(4-[[tert-butyl(dimethyl)silyl]oxy]phenoxy)-2-propanol | C23H36N2O3Si | 详情 | 详情 | |
| (VIII) | 18963 | tert-butyl 4-aminophenethyl[(2S)-3-(4-[[tert-butyl(dimethyl)silyl]oxy]phenoxy)-2-hydroxypropyl]carbamate | C28H44N2O5Si | 详情 | 详情 | |
| (IX) | 18964 | 4-bromobenzenesulfonyl chloride | 98-58-8 | C6H4BrClO2S | 详情 | 详情 |
| (X) | 18965 | tert-butyl 4-[[(4-bromophenyl)sulfonyl]amino]phenethyl[(2S)-3-(4-[[tert-butyl(dimethyl)silyl]oxy]phenoxy)-2-hydroxypropyl]carbamate | C34H47BrN2O7SSi | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(II)The reaction of 3-hydroxypyridine (I) with (S)-glycidol 3-nitrobenzenesulfonate (II) by means of sodium hexamethyldisylazide in DMSO gives 2(S)-(3-pyridyloxymethyl)oxirane (III), which is condensed with 2-(4-nitrophenyl)ethylamine (IV) by means of triethylamine in refluxing methanol yielding the chiral isopropanol (V). The protection of the secondary amino group of (V) with tert-butoxycarbonyl anhydride affords the carbamate (VI), which is submitted to reduction at the nitro group with H2 over palladium hydroxide in ethyl acetate providing the aniline derivative (VII). The acylation of (VII) with 4-iodobenzenesulfonyl chloride (VIII) and pyridine in dichloromethane affords the sulfonamide (IX), which is finally deprotected with 6N HCl in methanol.
| 【1】 Fisher, M.H.; Mathvink, R.J.; Ok, H.O.; Parmee, E.R.; Weber, A.E. (Merck & Co., Inc.); Substd. phenyl sulfonamides as selective beta3 agonists for the treatment of diabetes and obesity. CA 2114712; EP 0611003; JP 1995010827; US 5451677; WO 9418161 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 12911 | 3-Hydroxypyridine; 3-Pyridinol | 109-00-2 | C5H5NO | 详情 | 详情 |
| (II) | 16259 | (2S)oxiranylmethyl 3-nitrobenzenesulfonate; (S)-(+)-Glycidyl nosylate | 115314-14-2 | C9H9NO6S | 详情 | 详情 |
| (III) | 27807 | (2S)oxiranylmethyl 3-pyridinyl ether | C8H9NO2 | 详情 | 详情 | |
| (IV) | 26560 | 4-nitrophenethylamine | 24954-67-4 | C8H10N2O2 | 详情 | 详情 |
| (V) | 27808 | (2S)-1-[(4-nitrophenethyl)amino]-3-(3-pyridinyloxy)-2-propanol | C16H19N3O4 | 详情 | 详情 | |
| (VI) | 27809 | tert-butyl (2S)-2-hydroxy-3-(3-pyridinyloxy)propyl(4-nitrophenethyl)carbamate | C21H27N3O6 | 详情 | 详情 | |
| (VII) | 27810 | tert-butyl 4-aminophenethyl[(2S)-2-hydroxy-3-(3-pyridinyloxy)propyl]carbamate | C21H29N3O4 | 详情 | 详情 | |
| (VIII) | 27811 | 4-iodobenzenesulfonyl chloride | 98-61-3 | C6H4ClIO2S | 详情 | 详情 |
| (IX) | 27812 | tert-butyl (2S)-2-hydroxy-3-(3-pyridinyloxy)propyl(4-[[(4-iodophenyl)sulfonyl]amino]phenethyl)carbamate | C27H32IN3O6S | 详情 | 详情 |
合成路线5
该中间体在本合成路线中的序号：(II)The reaction of 2-acetamido-5-hydroxypyridine (I) with (S)-glycidol 3-nitrobenzenesulfonate (II) by means of NaOH in DMF gives 2(S)-(6-acetamido-3-pyridyloxymethyl)oxirane (III), which is condensed with 2-(4-nitrophenyl)ethylamine (IV) by means of triethylamine in refluxing methanol yielding the chiral isopropanol (V). The protection of the secondary amino group of (V) with tert-butoxycarbonyl anhydride affords the carbamate (VI), which is submitted to reduction at the nitro group with H2 over Pd/C in ethyl acetate providing the aniline derivative (VII). The acylation of (VII) with 4-iodobenzenesulfonyl chloride (VIII) and pyridine in dichloromethane affords the sulfonamide (IX), which is finally deprotected with 2N HCl in refluxing methanol.
| 【1】 Fisher, M.H.; Mathvink, R.J.; Ok, H.O.; Parmee, E.R.; Weber, A.E. (Merck & Co., Inc.); Substd. phenyl sulfonamides as selective beta3 agonists for the treatment of diabetes and obesity. CA 2114712; EP 0611003; JP 1995010827; US 5451677; WO 9418161 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 27813 | N-(5-hydroxy-2-pyridinyl)acetamide | C7H8N2O2 | 详情 | 详情 | |
| (II) | 16259 | (2S)oxiranylmethyl 3-nitrobenzenesulfonate; (S)-(+)-Glycidyl nosylate | 115314-14-2 | C9H9NO6S | 详情 | 详情 |
| (III) | 27814 | N-[5-[(2S)oxiranylmethoxy]-2-pyridinyl]acetamide | C10H12N2O3 | 详情 | 详情 | |
| (IV) | 26560 | 4-nitrophenethylamine | 24954-67-4 | C8H10N2O2 | 详情 | 详情 |
| (V) | 27815 | N-[5-([(2S)-2-hydroxy-3-[(4-nitrophenethyl)amino]propyl]oxy)-2-pyridinyl]acetamide | C18H22N4O5 | 详情 | 详情 | |
| (VI) | 27816 | tert-butyl (2S)-3-[[6-(acetamido)-3-pyridinyl]oxy]-2-hydroxypropyl(4-nitrophenethyl)carbamate | C23H30N4O7 | 详情 | 详情 | |
| (VII) | 27817 | tert-butyl (2S)-3-[[6-(acetamido)-3-pyridinyl]oxy]-2-hydroxypropyl(4-aminophenethyl)carbamate | C23H32N4O5 | 详情 | 详情 | |
| (VIII) | 28870 | 4-isopropylbenzenesulfonyl chloride | 54997-90-9 | C9H11ClO2S | 详情 | 详情 |
| (IX) | 27818 | tert-butyl (2S)-3-[[6-(acetamido)-3-pyridinyl]oxy]-2-hydroxypropyl(4-[[(4-isopropylphenyl)sulfonyl]amino]phenethyl)carbamate | C32H42N4O7S | 详情 | 详情 |
合成路线6
该中间体在本合成路线中的序号：(V)NPS-2143 can be obtained by coupling 2-chloro-6-[2(R)-oxiranylmethoxy]benzonitrile (I) with 1,1-dimethyl-2-(2-naphthyl)ethylamine (II) in ethanol at 50-60 C. Intermediates (I) and (II) can be obtained as follows: a) Treatment of 2-chloro-6-fluorobenzonitrile (III) with 18-crown-6 and potassium acetate in refluxing acetonitrile, followed by hydrolysis with NaOH in H2O provides 3-chloro-2-cyanophenol (IV), which is then condensed with 3-nitrobenzenesulfonic acid (2R)-2-oxiranylmethyl ester (V) in DMF by means of NaH to furnish 2-chloro-6-[2(R)-oxiranylmethoxy]benzonitrile (I). b) Treatment of 2-(aminomethyl)naphthalene (VI) with 2,4,6-triphenylpyrylium tetrafluoroborate in EtOH, followed by the reaction of the resulting compound dissolved in DMSO with the sodium salt obtained by treatment of 2-nitropropane (VII) with NaH in MeOH, gives the nitro derivative (VIII). Finally, reduction of the nitro group of (VIII) by hydrogenation over Ni Raney in EtOH yields 1,1,-dimethyl-2-(2-naphthyl)ethylamine (II).
| 【2】 Sheehan, D.; Del Mar, E.G.; Lago, M.A.; Southall, L.S.; Callahan, J.F.; Kotecha, N.R.; Thompson, M.; Barmore, R.M.; Keenan, R.M.; Van Wagenen, B.C. (GlaxoSmithKline Inc.; GlaxoSmithKline plc; NPS Pharmaceuticals, Inc.); Method of using calcilytic cpds.. US 6022894 . |
| 【1】 del Fresno, M.; Doggrell, S.A.; Castaner, J.; NPS-2143. Drugs Fut 2002, 27, 2, 140. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 51708 | C23H17BF4O | 详情 | 详情 | |||
| (I) | 51706 | 2-chloro-6-[(2R)oxiranylmethoxy]benzonitrile | C10H8ClNO2 | 详情 | 详情 | |
| (II) | 51710 | 1,1-dimethyl-2-(2-naphthyl)ethylamine; 2-methyl-1-(2-naphthyl)-2-propanamine | C14H17N | 详情 | 详情 | |
| (III) | 51704 | 2-Chloro-6-fluorobenzonitrile; 2-Fluoro-6-chlorobenzonitrile | 668-45-1 | C7H3ClFN | 详情 | 详情 |
| (IV) | 51705 | 2-chloro-6-hydroxybenzonitrile | C7H4ClNO | 详情 | 详情 | |
| (V) | 16259 | (2S)oxiranylmethyl 3-nitrobenzenesulfonate; (S)-(+)-Glycidyl nosylate | 115314-14-2 | C9H9NO6S | 详情 | 详情 |
| (VI) | 51707 | 2-naphthylmethanamine; 2-naphthylmethylamine | C11H11N | 详情 | 详情 | |
| (VII) | 21819 | 2-nitropropane | 79-46-9 | C3H7NO2 | 详情 | 详情 |
| (VIII) | 51709 | 2-(2-methyl-2-nitropropyl)naphthalene | C14H15NO2 | 详情 | 详情 |
合成路线7
该中间体在本合成路线中的序号：(XI)By condensation of substituted nicotinamide (VI) with the carbazolyoxymethyl-oxirane (XII) in hot methanol/water. The intermediates the nicotinamide (VI) and the oxirane (XII) have been obtained as follows: 1.- Nicotinamide (VI): The reaction of 4-hydroxybenzyl alcohol (I) with 2-nitropropane (II) by means of potassium tert-butoxide in hot diglyme gives 4-(2-methyl-2-nitropropyl)phenol (III), which is reduced to the corresponding amino derivative (IV) with H2 over Pd/C in methanol/ethanol/acetic acid. Finally, this compound is condensed with 6-chloronicotinamide (V) by means of K2CO3 in dimethylacetamide/isooctane. 2.- Oxirane (XII): The reaction of phenylhydrazine (VII) with cyclohexane-1,3-dione (VIII) by means of NaHCO3 in isopropanol/water gives the monohydrazone (IX), which is cyclized with hotpolyphosphoric acid yielding the 4-hydroxycarbazole (X). Finally, this compound is condensed with the glycidyl 3-nitrophenylsulfonate (XI) by means of K2CO3 in refluxing acetone.
| 【1】 Crowell, T.A.; Evrard, D.A.; Jones, C.D.; Muehl, B.S.; Rito, C.J.; Shuker, A.J.; Thorpe, A.J.; Thrasher, K.J. (Eli Lilly and Company); Carbazole analogues as selective B3 adrenergic agonists. EP 0827746; WO 9809625 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 29474 | 4-(hydroxymethyl)phenol; 4-hydroxyphenylmethanol 4-hydroxybenzenemethanol; 4-Hydroxybenzyl alcohol | 623-05-2 | C7H8O2 | 详情 | 详情 |
| (II) | 21819 | 2-nitropropane | 79-46-9 | C3H7NO2 | 详情 | 详情 |
| (III) | 29475 | 4-(2-methyl-2-nitropropyl)phenol | C10H13NO3 | 详情 | 详情 | |
| (IV) | 29476 | 4-(2-amino-2-methylpropyl)phenol | 51706-55-9 | C10H15NO | 详情 | 详情 |
| (V) | 29477 | 6-chloronicotinamide | 6271-78-9 | C6H5ClN2O | 详情 | 详情 |
| (VI) | 29478 | 6-[4-(2-amino-2-methylpropyl)phenoxy]nicotinamide | C16H19N3O2 | 详情 | 详情 | |
| (VII) | 11818 | Phenyl hydrazine; 1-Phenylhydrazine | 100-63-0 | C6H8N2 | 详情 | 详情 |
| (VIII) | 11244 | 1,3-Cyclohexanedione | 504-02-9 | C6H8O2 | 详情 | 详情 |
| (IX) | 29479 | 3-hydroxy-2-cyclohexen-1-one N-phenylhydrazone | C12H14N2O | 详情 | 详情 | |
| (X) | 29480 | 4-Hydroxycarbazole; 9H-carbazol-4-ol | 52602-39-8 | C12H9NO | 详情 | 详情 |
| (XI) | 16259 | (2S)oxiranylmethyl 3-nitrobenzenesulfonate; (S)-(+)-Glycidyl nosylate | 115314-14-2 | C9H9NO6S | 详情 | 详情 |
| (XII) | 29481 | 9H-carbazol-4-yl (2S)oxiranylmethyl ether; 4-[(2S)oxiranylmethoxy]-9H-carbazole | C15H13NO2 | 详情 | 详情 |