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【结 构 式】 
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【分子编号】38403 【品名】4-fluorophenylboronic acid 【CA登记号】1765-93-1 |
【 分 子 式 】C6H6BFO2 【 分 子 量 】139.9218432 【元素组成】C 51.5% H 4.32% B 7.73% F 13.58% O 22.87% |
合成路线1
该中间体在本合成路线中的序号：The biphenyl side chain of LY293111 can be constructed as illustrated in Scheme 19757001a: 4-Benzyloxy-2-hydroxyacetophenone (I) is alkylated with 1-bromo-3-chloropropane to provide compound (II). Reduction of the keto group with triethylsilane in trifluoroacetic acid provides (III), which is then regiospecifically brominated with N-bromosuccinimide to give (IV). A Suzuki biaryl coupling of (IV) with 4-fluorophenylboronic acid is used to prepare chloride (V), which is treated with sodium iodide in refluxing 2-butanone to give intermediate iodide (VI).
| 【1】 Schmittling, E.A.; Sawyer, J.S.; Synthesis of diaryl ethers, diaryl thioethers, and diaryl amines mediated by potassium fluoride-alumina and 18-crown-6. J Org Chem 1993, 58, 3229-30. |
| 【2】 Sawyer, J.S.; Bach, N.J.; Baker, S.R.; et al.; Synthetic and structure/activity studies on acid-substituted 2-arylphenols: The discovery of 2-[2-propyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]propoxy]phenoxy]benzoic acid, a high-affinity leukotriene B4 receptor antagonist. J Med Chem 1995, 38, 22, 4411-32. |
| 【3】 Sawyer, J.S.; Baldwin, R.F.; Sofia, M.J.; et al.; Biphenylyl-substituted xanthones: Highly potent leukotriene B4 receptor antagonists. J Med Chem 1993, 36, 24, 3982-4. |
| 【4】 Sawyer, J.S.; LY-293111 Sodium. Drugs Fut 1996, 21, 6, 610. |
| 【5】 Sawyer, J.S.; Baldwin, R.F.; Saussy, D.L. Jr.; Froelich, L.L.; Jackson, W.T.; Diaryl ether/carboxylic acid derivatives of LY255283: Receptor antagonists of leukotriene B4. Bioorg Med Chem Lett 1993, 3, 10, 1985-90. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 10358 | 1-Bromo-3-chloropropane | 109-70-6 | C3H6BrCl | 详情 | 详情 | |
| 38403 | 4-fluorophenylboronic acid | 1765-93-1 | C6H6BFO2 | 详情 | 详情 | |
| (I) | 16208 | 4'-Benzyloxy-2'-hydroxyacetophenone; 1-[4-(Benzyloxy)-2-hydroxyphenyl]-1-ethanone | 29682-12-0 | C15H14O3 | 详情 | 详情 |
| (II) | 16209 | 1-[4-(benzyloxy)-2-(3-chloropropoxy)phenyl]-1-ethanone | C18H19ClO3 | 详情 | 详情 | |
| (III) | 16210 | 4-(benzyloxy)-2-(3-chloropropoxy)-1-ethylbenzene; benzyl 3-(3-chloropropoxy)-4-ethylphenyl ether | C18H21ClO2 | 详情 | 详情 | |
| (IV) | 16211 | benzyl 2-bromo-5-(3-chloropropoxy)-4-ethylphenyl ether; 1-(benzyloxy)-2-bromo-5-(3-chloropropoxy)-4-ethylbenzene | C18H20BrClO2 | 详情 | 详情 | |
| (V) | 16212 | benzyl 4-(3-chloropropoxy)-5-ethyl-4'-fluoro[1,1'-biphenyl]-2-yl ether; 2-(benzyloxy)-4-(3-chloropropoxy)-5-ethyl-4'-fluoro-1,1'-biphenyl | C24H24ClFO2 | 详情 | 详情 | |
| (VI) | 16213 | benzyl 5-ethyl-4'-fluoro-4-(3-iodopropoxy)[1,1'-biphenyl]-2-yl ether; 2-(benzyloxy)-5-ethyl-4'-fluoro-4-(3-iodopropoxy)-1,1'-biphenyl | C24H24FIO2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(V)Aldol condensation between dimethyl 1,3-acetonedicarboxylate (I) and 3,5-heptanedione (II) produced dimethyl 4,6-diethyl-2-hydroxy-1,3-benzenedicarboxylate (III). After conversion of phenol (III) to the corresponding aryl triflate (IV), Suzuki coupling with 4-fluorobenzeneboronic acid (V) yielded the biphenyl derivative (VI). The diisopropyl compound (VII) was then obtained by methylation of (VI) at the benzylic position using iodomethane and LDA. Partial reduction of diester (VII) with Red-Al?gave rise to the hydroxy ester (VIII), which was further oxidized to aldehyde (IX) by treatment with pyridinium chlorochromate. Wittig reaction of aldehyde (IX) with ethyl triphenylphosphonium bromide furnished the propenyl compound (X)
| 【2】 Schmidt, G.; Wolanin, D.J.; Bischoff, H.; Schoen, W.R.; Angerbauer, R.; Schmidt, D.; Kramss, R.H.; Wohlfeil, S.; Brandes, A.; Muller-Gliemann, M.; Lease, T.G.; Ladouceur, G.H.; Osterhout, M.H.; Hertzog, D.L.; Cook, J.H. II (Bayer AG; Bayer Corp.); Substd. pyridines and biphenyls as anti-hypercholesterinemic, anti-hyperlipoproteinemic and anti-hyperglycemic agents. WO 9804528 . |
| 【1】 Wolanin, D.J.; Schoen, W.R.; Kramss, R.H.; Lease, T.G.; Ladouceur, G.H.; Osterhout, M.H.; Hertzog, D.L.; Cook, J.H. II (Bayer AG; Bayer Corp.); Substd. biphenyls. US 6218431 . |
| 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) | 22692 | dimethyl 3-oxopentanedioate | 1830-54-2 | C7H10O5 | 详情 | 详情 |
| (II) | 39689 | 3,5-heptanedione | 7424-54-6 | C7H12O2 | 详情 | 详情 |
| (III) | 60521 | dimethyl 4,6-diethyl-2-hydroxyisophthalate | C14H18O5 | 详情 | 详情 | |
| (IV) | 60522 | dimethyl 4,6-diethyl-2-{[(trifluoromethyl)sulfonyl]oxy}isophthalate | C15H17F3O7S | 详情 | 详情 | |
| (V) | 38403 | 4-fluorophenylboronic acid | 1765-93-1 | C6H6BFO2 | 详情 | 详情 |
| (VI) | 60523 | dimethyl 3,5-diethyl-4'-fluoro[1,1'-biphenyl]-2,6-dicarboxylate | C20H21FO4 | 详情 | 详情 | |
| (VII) | 60524 | dimethyl 4'-fluoro-3,5-diisopropyl[1,1'-biphenyl]-2,6-dicarboxylate | C22H25FO4 | 详情 | 详情 | |
| (VIII) | 60525 | methyl 4'-fluoro-6-(hydroxymethyl)-3,5-diisopropyl[1,1'-biphenyl]-2-carboxylate | C21H25FO3 | 详情 | 详情 | |
| (IX) | 60526 | methyl 4'-fluoro-6-formyl-3,5-diisopropyl[1,1'-biphenyl]-2-carboxylate | C21H23FO3 | 详情 | 详情 | |
| (X) | 60527 | methyl 4'-fluoro-3,5-diisopropyl-6-[(E)-1-propenyl][1,1'-biphenyl]-2-carboxylate | C23H27FO2 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(II)This compound has been obtained by condensation of 1-(4-bromobenzyl)imidazole (I) with 4-fluorophenylboronic acid (II) by means of Pd(PPh3)4 and Na2CO3 in refluxing toluene/ethanol.
| 【1】 Wachall, B.G.; et al.; Imidazole substituted biphenyls: A new class of highly potent and in vivo active inhibitors of P450 17 as potential therapeutics for treatment of prostate cancer. Bioorg Med Chem 1999, 7, 9, 1913. |
合成路线4
该中间体在本合成路线中的序号：(IV)(S)-7-Hydroxy-1,2,3,4-tetrahydroqinoline-3-carboxylic acid (I) is N-protected by means of di-tert-butyldicarbonate (Boc2O) and Na2CO3 in H2O/dioxane and then converted into methyl ester derivative (II) by treatment with trimethylsilyl diazomethane (TMSCNH2). Reaction of (II) with triflic anhydride (Tf2O) and Et3N in CH2Cl2 yields triflate (III), which is then coupled to boronic acid (IV) by Suzuki cross-coupling reaction in the presence of Pd(PPh3)4 and Na2CO3 in toluene/EtOH, providing derivative (V). Boc removal in (V) by treatment with HCl/HOAc followed by coupling with N-Boc-2,6-dimethyl-D/L-tyrosine (VIa-b) by means of EDC, HOBt, DIEA and DMAP in DMF furnishes protected compound (VIIa-b). Compound (VIIa-b) is hydrolyzed with LiOH and N-deprotected by means of HCl/HOAc to afford a mixture of diastereomers (VIIIa-b) from which the target compound is separated by reverse-phase HPLC.
| 【1】 Brown, W.; Mischki, T.; Butterworth, J.; Schmidt, R.; McGlory, A.; Payza, K.; St-Onge, S.; Labarre, M.; Pagé, D.; Novel Dmt-Tic dipeptide analogues as selective delta-opioid receptor antagonists. Bioorg Med Chem Lett 2000, 10, 2, 167. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIIa) | 44185 | 5,6-diamino-3-methyl-1-phenyl-2,4(1H,3H)-pyrimidinedione | C11H12N4O2 | 详情 | 详情 | |
| (VIa) | 44813 | (2R)-2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxy-2,6-dimethylphenyl)propionic acid | C16H23NO5 | 详情 | 详情 | |
| (VIb) | 44814 | (2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxy-2,6-dimethylphenyl)propionic acid | C16H23NO5 | 详情 | 详情 | |
| (VIIb) | 44816 | methyl (3S)-2-[(2R)-2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxy-2,6-dimethylphenyl)propanoyl]-7-(4-fluorophenyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate | C33H37FN2O6 | 详情 | 详情 | |
| (VIIIa) | 44817 | (3S)-2-[(2R)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanoyl]-7-(4-fluorophenyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid | C27H27FN2O4 | 详情 | 详情 | |
| (VIIIb) | 44818 | (3S)-2-[(2S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanoyl]-7-(4-fluorophenyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid | C27H27FN2O4 | 详情 | 详情 | |
| (I) | 44809 | (3S)-7-hydroxy-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid | 128502-56-7 | C10H11NO3 | 详情 | 详情 |
| (II) | 44810 | 2-(tert-butyl) 3-methyl (3S)-7-hydroxy-3,4-dihydro-2,3(1H)-isoquinolinedicarboxylate | C16H21NO5 | 详情 | 详情 | |
| (III) | 44811 | 2-(tert-butyl) 3-methyl (3S)-7-[[(trifluoromethyl)sulfonyl]oxy]-3,4-dihydro-2,3(1H)-isoquinolinedicarboxylate | C17H20F3NO7S | 详情 | 详情 | |
| (IV) | 38403 | 4-fluorophenylboronic acid | 1765-93-1 | C6H6BFO2 | 详情 | 详情 |
| (V) | 44812 | 2-(tert-butyl) 3-methyl (3S)-7-(4-fluorophenyl)-3,4-dihydro-2,3(1H)-isoquinolinedicarboxylate | C22H24FNO4 | 详情 | 详情 |
合成路线5
该中间体在本合成路线中的序号：(VII)Condensation of methyl indole-4-carboxylate (I) with 2-nitroethyl acetate (II) produced the 3-nitroethyl indole (III). After reduction of the nitro group to amine (IV) using Zn and HCl, cyclization under basic conditions gave rise to lactam (V). Electrophilic bromination of (V) employing pyridinium tribromide furnished (VI). Finally, Suzuki coupling of bromide (VI) with 4-fluorobenzeneboronic acid (VII) yielded the title compound.
| 【1】 Thoresen, L.H.; Webber, S.E.; Tikhe, J.; Canan-Koch, S.S. (Agouron Pharmaceuticals, Inc.; Cancer Research Campaign Technology Ltd.); Tricyclic inhibitors of poly(ADP-ribose) polymerases. EP 1140936; WO 0042040 . |
| 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) | 50446 | Indole-4-carboxylic acid methyl ester | 39830-66-5 | C10H9NO2 | 详情 | 详情 |
| (II) | 50447 | 2-nitroethyl acetate | C4H7NO4 | 详情 | 详情 | |
| (III) | 50448 | methyl 3-(2-nitroethyl)-1H-indole-4-carboxylate | C12H12N2O4 | 详情 | 详情 | |
| (IV) | 50449 | methyl 3-(2-aminoethyl)-1H-indole-4-carboxylate | C12H14N2O2 | 详情 | 详情 | |
| (V) | 50450 | 1,3,4,5-tetrahydro-6H-azepino[5,4,3-cd]indol-6-one | C11H10N2O | 详情 | 详情 | |
| (VI) | 50451 | 2-bromo-1,3,4,5-tetrahydro-6H-azepino[5,4,3-cd]indol-6-one | C11H9BrN2O | 详情 | 详情 | |
| (VII) | 38403 | 4-fluorophenylboronic acid | 1765-93-1 | C6H6BFO2 | 详情 | 详情 |
合成路线6
该中间体在本合成路线中的序号：(VI)3,4-Dimethoxybenzoic acid (I) is converted into oxazoline (II) by known methods. This compound is treated with BuLi and I2 in ethyl ether to yield the 2-iodo derivative (III), which is treated with POCl3 in hot pyridine to afford 2-iodo-3,4-dimethoxybenzonitrile (IV). The nitration of (IV) by means of nitronium tetrafluoroborate in acetonitrile provides 2-iodo-3,4-dimethoxy-6-nitrobenzonitrile (V), which is condensed with 4-fluorophenylboronic acid (VI) by means of Pd(PPh3)4 in toluene/ethanol to give the biphenyl derivative (VII). The reduction of the nitro group of (VII) by means of sodium dithionite in DMF/water yields the corresponding amino derivative (VIII), which is condensed with 1-acetyl-4-(morpholin-4-ylcarbonyl)perhydro-1,4-diazepine (IX) by means of POCl3 in dichloromethane to afford the adduct (X). Finally, this compound is cyclized by means of LDA in THF to provide the target quinoline derivative. The intermediate 1-acetyl-4-(morpholin-4-ylcarbonyl)perhydro-1,4-diazepine (IX) has been obtained as follows: The reaction of perhydro-1,4-diazepine (XI) with Boc2O in dichloromethane gives the monoprotected diazepine (XII), which is condensed with morpholin-4-yl-carbonyl chloride (XIII) by means of TEA in dichloromethane to yield the acylated diazepine (XIV). The deprotection of (XIV) by means of HCl in dichloromethane/methanol affords the deprotected diazepine (XV), which is finally acylated with acetic anhydride and TEA in dichloromethane to provide the target intermediate (IX).
| 【1】 Collis, A.J.; Fox, D.N.A.; Newman, J. (Pfizer Inc.); Quinoline and quinazoline cpds. useful in therapy. EP 0877734; JP 1999501668; US 6103738; WO 9723462 . |
| 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) | 13439 | 3,4-Dimethoxybenzoic acid | 93-07-2 | C9H10O4 | 详情 | 详情 |
| (II) | 54071 | 2-(3,4-dimethoxyphenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole; 4-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)-2-methoxyphenyl methyl ether | n/a | C13H17NO3 | 详情 | 详情 |
| (III) | 54072 | 2-(2-iodo-3,4-dimethoxyphenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole; 3-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)-2-iodo-6-methoxyphenyl methyl ether | n/a | C13H16INO3 | 详情 | 详情 |
| (IV) | 54073 | 2-iodo-3,4-dimethoxybenzonitrile | n/a | C9H8INO2 | 详情 | 详情 |
| (V) | 54074 | 2-iodo-3,4-dimethoxy-6-nitrobenzonitrile | n/a | C9H7IN2O4 | 详情 | 详情 |
| (VI) | 38403 | 4-fluorophenylboronic acid | 1765-93-1 | C6H6BFO2 | 详情 | 详情 |
| (VII) | 54075 | 4'-fluoro-5,6-dimethoxy-3-nitro[1,1'-biphenyl]-2-carbonitrile | n/a | C15H11FN2O4 | 详情 | 详情 |
| (VIII) | 54076 | 3-amino-4'-fluoro-5,6-dimethoxy[1,1'-biphenyl]-2-carbonitrile | n/a | C15H13FN2O2 | 详情 | 详情 |
| (IX) | 54077 | 1-[4-(4-morpholinylcarbonyl)-1,4-diazepan-1-yl]-1-ethanone | n/a | C12H21N3O3 | 详情 | 详情 |
| (X) | 54078 | 4'-fluoro-5,6-dimethoxy-3-({(E)-1-[4-(4-morpholinylcarbonyl)-1,4-diazepan-1-yl]ethylidene}amino)[1,1'-biphenyl]-2-carbonitrile | n/a | C27H32FN5O4 | 详情 | 详情 |
| (XI) | 25030 | 1,4-diazepane | 505-66-8 | C5H12N2 | 详情 | 详情 |
| (XII) | 54079 | tert-Butyl 1-homopiperazine carboxylate | n/a | C10H20N2O2 | 详情 | 详情 |
| (XIII) | 15847 | 4-morpholinecarbonyl chloride; Morpholine-4-carbonyl chloride | 15159-40-7 | C5H8ClNO2 | 详情 | 详情 |
| (XIV) | 54080 | tert-butyl 4-(4-morpholinylcarbonyl)-1,4-diazepane-1-carboxylate | n/a | C15H27N3O4 | 详情 | 详情 |
| (XV) | 54081 | 1,4-diazepan-1-yl(4-morpholinyl)methanone | n/a | C10H19N3O2 | 详情 | 详情 |
合成路线7
该中间体在本合成路线中的序号：(XX)In one method, metalation of 1-bromo-4-fluorobenzene (XI) with Mg in 2-MeTHF at 90 °C gives 4-fluorophenyl magnesium bromide (XII), which then couples with 2-bromothiophene (XIII) in the presence of NiCl2·dppe and AcOH in 2-MeTHF at 22 °C or in the presence of Pd(OAc)2 and DPPP in THF to yield 2-(4-fluorophenyl)thiophene (XIV). Finally, this compound undergoes Friedel–Crafts acylation with 5-iodo-2-methylbenzoic acid (XV) (initially chlorinated with SOCl2 in CH2Cl2) using AlCl3 in CH2Cl2, and subsequent reduction with (Me2SiH)2O in refluxing acetonitrile .
In another method, hydrolysis of methyl 5-bromo-2-methylbenzoate (XVI) with NaOH in MeOH at 50 °C gives rise to the benzoic acid (XVII) , which is then chlorinated with (COCl)2 in the presence of DMF in CH2Cl2 to yield 5-bromo-2-methylbenzoyl chloride (XVIII). Friedel–Crafts reaction of acyl chloride (XVIII) with 2-(4-fluorophenyl) thiophene (XIV) in the presence of AlCl3 in CH2Cl2 affords ketone (XIX), which is then reduced by means of Et3SiH and BF3·Et2O in CH2Cl2/acetonitrile to afford 2-(5-bromo-2-methylbenzoyl)-5-(4-fluorophenyl)thiophene (III) . Finally, compound (III) is iodinated with NaI and CuI in the presence of (MeNHCH2)2 in refluxing toluene/diglyme (IV) .
Alternatively, coupling of 4-fluorophenylboronic acid (XX) with either 2-bromothiophene (XIII) in the presence of PdCl2(PPh3)2 and Na2CO3 in dimethoxyethane at 75-80 °C or with 2-iodothiophene (XXI) in the presence of PdCl2(PPh3)2 at 50 °C affords 2-(4-fluorophenyl) thiophene (XIV) .
| 【1】 Abdel-Magid, A.F., Chisholm, M., Mehrman, S. et al. (Janssen Pharmaceutica NV; Mitsubishi Tanabe Pharma Corp.). Process for the preparation of compounds useful as inhibitors of SGLT. CN 101801371, EP 2200606, JP 2010539092, WO 2009035969. |
| 【2】 Nomura, S., Ueta, K., Kawanishi, E. (Mitsubishi Tanabe Pharma Corp.). Novel compounds having inhibitory activity against sodium-dependant transporter. EP 1651658, JP 2007518683, JP 2008266328, WO 2005012326. |
| 【3】 Nomura, S., Sakamaki, S., Hongu, M. et al. Discovery of canagliflozin, a novel C-glucoside with thiophene ring, as sodium-dependent glucose cotransporter 2 inhibitor for the treatment of type 2 diabetes mellitus. J Med Chem 2010, 53(17): 6355-60. |
| 【4】 Filliers, W.F.M., Broeckx, R.L.M., Nieste, P.H.J., Hatsuda, M., Yoshinaga, M., Yada, M. (Janssen Pharmaceutica NV; Mitsubishi Tanabe Pharma Corp.). Process for the preparation of compounds useful as inhibitors of SGLT. US 2010099883, WO 2010043682. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (III) | 68782 | 2-(5-bromo-2-methylbenzyl)-5-(4-fluorophenyl)thiophene | 1030825-20-7 | C18H14BrFS | 详情 | 详情 |
| (IV) | 68783 | 2-(4-fluorophenyl)-5-(5-iodo-2-methylbenzyl)thiophene | 898566-17-1 | C18H14FIS | 详情 | 详情 |
| (XI) | 29012 | 1-bromo-4-fluorobenzene | 460-00-4 | C6H4BrF | 详情 | 详情 |
| (XII) | 13643 | 4-fluorophenyl magnesium bromide;Bromo(4-fluorophenyl)magnesium;bromo(p-fluorophenyl)Magnesium;p-Fluorophenylmagnesium bromide | 352-13-6 | C6H4BrFMg | 详情 | 详情 |
| (XIII) | 13681 | 2-Bromothiophene | 1003-09-4 | C4H3BrS | 详情 | 详情 |
| (XIV) | 68790 | 2-(4-fluorophenyl)thiophene | 58861-49-7 | C10H7FS | 详情 | 详情 |
| (XV) | 68791 | 5-iodo-2-methylbenzoic acid;2-Methyl-5-iodobenzoicacid | 54811-38-0 | C8H7IO2 | 详情 | 详情 |
| (XVI) | 68792 | methyl 5-bromo-2-methylbenzoate;methyl 5-bromo-o-toluate | 79669-50-4 | C9H9BrO2 | 详情 | 详情 |
| (XVII) | 68793 | 5-bromo-2-methylbenzoic acid;2-Methyl-5-bromobenzoic acid | 79669-49-1 | C8H7BrO2 | 详情 | 详情 |
| (XVIII) | 68794 | 5-bromo-2-methylbenzoyl chloride | C8H6BrClO | 详情 | 详情 | |
| (XIX) | 68795 | (5-bromo-2-methylphenyl)(5-(4-fluorophenyl)thiophen-2-yl)methanone | C18H12BrFOS | 详情 | 详情 | |
| (XX) | 38403 | 4-fluorophenylboronic acid | 1765-93-1 | C6H6BFO2 | 详情 | 详情 |
| (XXI) | 43394 | 2-iodothiophene | 3437-95-4 | C4H3IS | 详情 | 详情 |