Sertraline, CP-51974-1, CP-5197401(hydrochloride), -Drug Synthesis Database

【结构式】

【药物名称】Sertraline, CP-51974-1, CP-5197401(hydrochloride)

【化学名称】(1S-cis)-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine
　　　　　　(1S,4S)-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthylamine

【CA登记号】79617-96-2, 79559-97-0 (HCl)

【分子式】C₁₇H₁₇Cl₂N

【分子量】306.23774

【开发单位】Pfizer (Originator)

【药理作用】Antidepressants, Mood Disorders, Treatment of, PSYCHOPHARMACOLOGIC DRUGS, 5-HT Reuptake Inhibitors

合成路线1 合成路线2 合成路线3 合成路线4 合成路线5 合成路线6 合成路线7 合成路线8

合成路线1

A new synthesis of [7-3H]-sertraline has been described: The optical resolution of 7-bromo-1-(methylamino)tetraline (I) with N-acetyl-D-phenylalanine gives the (R)-isomer (II), which is acylated with formic acid - acetic anhydride to the formamide (III). The oxidation of (III) with KMnO4 in acetone - water yields 6-bromo-4(R)-(methylamino)-1,2,3,4-tetrahydronaphthalen-1-one (IV), which, by a Grignard condensation with 3,4-dichlorophenylmagnesium bromide (V) in ether - toluene, affords 6-bromo-1(S)-(3,4-dichlorophenyl)-4(R)-(N-methylformamido)-1,2,3,4-tetrahydronaphthalen-1-ol (VI). The reduction of (VI) with triethylsilane tetrafluoroborate in dichloromethane gives 6-bromo-1(S)-(3,4-dichlorophenyl)-4(R)-(N-methylformamido)tetraline (VII), which is hydrolyzed with HCl in isopropanol to the corresponding methylamine (VIII). Oxidation of (VIII) with NaClO NaOCH3 in methanol - water yields the imine (IX), which is reduced with NaBH4 in THF - methanol to 6-bromo-1(S)-(3,4-dichlorophenyl)-4(S)-(methylamino)tetraline (X), along with starting (VIII). After separation by column chromatography, (X) is reduced with H2 over Pd/C or with T2 over Pd/C in THF containing triethylamine.

参考文献中间体

【1】 Williams, M.T.; Welch, W.M.; Synthesis of 7-3H-(IS,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-I-naphthalenamine hydrochloride (7-3H-sertraline). J Label Compd Radiopharm 1993, 33, 2, 119.

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)	10065	N-(7-Bromo-1,2,3,4-tetrahydro-1-naphthalenyl)-N-methylamine; 7-Bromo-N-methyl-1,2,3,4-tetrahydro-1-naphthalenamine		C₁₁H₁₄BrN	详情	详情
(II)	10066	(1R)-7-Bromo-N-methyl-1,2,3,4-tetrahydro-1-naphthalenamine; N-[(1R)-7-Bromo-1,2,3,4-tetrahydro-1-naphthalenyl]-N-methylamine		C₁₁H₁₄BrN	详情	详情
(III)	10067	N-[(1R)-7-Bromo-1,2,3,4-tetrahydro-1-naphthalenyl]-N-methylformamide		C₁₂H₁₄BrNO	详情	详情
(IV)	10068	N-[(1R)-7-Bromo-4-oxo-1,2,3,4-tetrahydro-1-naphthalenyl]-N-methylformamide		C₁₂H₁₂BrNO₂	详情	详情
(V)	10069	Bromo(3,4-dichlorophenyl)magnesium	79175-35-2	C₆H₃BrCl₂Mg	详情	详情
(VI)	10070	N-[(1R,4S)-7-Bromo-4-(3,4-dichlorophenyl)-4-hydroxy-1,2,3,4-tetrahydro-1-naphthalenyl]-N-methylformamide		C₁₈H₁₆BrCl₂NO₂	详情	详情
(VII)	10071	N-[(1R,4S)-7-Bromo-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenyl]-N-methylformamide		C₁₈H₁₆BrCl₂NO	详情	详情
(VIII)	10072	N-[(1R,4S)-7-Bromo-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenyl]-N-methylamine; (1R,4S)-7-Bromo-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydro-1-naphthalenamine		C₁₇H₁₆BrCl₂N	详情	详情
(IX)	10073	N-[(4S)-7-Bromo-4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine; N-[(4S)-7-Bromo-4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]-N-methylamine		C₁₇H₁₄BrCl₂N	详情	详情
(X)	10074	N-[(1S,4S)-7-Bromo-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenyl]-N-methylamine; (1S,4S)-7-Bromo-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydro-1-naphthalenamine		C₁₇H₁₆BrCl₂N	详情	详情

合成路线2

The Friedel-Kraft's reaction of benzene (I) and 3,4-dichlorobenzoyl chloride (II) by means of AlCl3 in dichloromethane gives 3,4-dichlorobenzophenone (III), which is condensed with diethyl succinate (IV) by means of potassium tert-butoxide in tert-butyl alcohol yielding ethyl 3-ethoxycarbonyl-4-(3,4-dichlorophenyl)-4-phenylbut-3-enoate (V). Hydrolysis of (V) with HBr in refluxing acetic acid affords 4-(3,4-dichlorophenyl)-4-phenylbut-3-enoic acid (VI), which is hydrogenated with H2 over Pd/C in ethyl acetate giving 4-(3,4-dichlorophenyl)-4-phenylbutanoic acid (VII), which is converted into the corresponding acyl chloride (VIII) with refluxing SOCl2. Cyclization of (VIII) with AlCl3 in CS2 yields 4-(3,4-dichlorophenyl)-3,4-dihydro-1-(2H)-naphthalenone (IX), which is treated with methylamine and TiCl4 in THF affording the corresponding Schiff base (X). Finally, this compound is reduced with H2 over Pd/C in THF.

参考文献中间体

【1】 Kraska, A.R.; Welch, W.M. Jr.; Koe, B.K.; Harbert, C.A. (Pfizer Inc.); Antidepressant derivatives of cis-4-phenyl-1,2,3,4-tetrahydro-1-naphtalenamine. EP 0030081; JP 1981086137; US 4536518 .
【2】 Castaner, J.; Serradell, M.N.; Sertraline. Drugs Fut 1984, 9, 4, 277.

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)	13364	Benzene	71-43-2	C₆H₆	详情	详情
(II)	26356	3,4-dichlorobenzoyl chloride	3024-72-4	C₇H₃Cl₃O	详情	详情
(III)	30578	(3,4-dichlorophenyl)(phenyl)methanone	6284-79-3	C₁₃H₈Cl₂O	详情	详情
(IV)	12313	diethyl succinate	123-25-1	C₈H₁₄O₄	详情	详情
(V)	30579	diethyl 2-[(Z)-(3,4-dichlorophenyl)(phenyl)methylidene]succinate		C₂₁H₂₀Cl₂O₄	详情	详情
(VI)	30580	(E)-4-(3,4-dichlorophenyl)-4-phenyl-3-butenoic acid		C₁₆H₁₂Cl₂O₂	详情	详情
(VII)	30581	4-(3,4-dichlorophenyl)-4-phenylbutyric acid		C₁₆H₁₄Cl₂O₂	详情	详情
(VIII)	30582	4-(3,4-dichlorophenyl)-4-phenylbutanoyl chloride		C₁₆H₁₃Cl₃O	详情	详情
(IX)	30583	4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone; 4-(3',4'-Dichlorophenyl)-1-tetralone	79580-19-3	C₁₆H₁₂Cl₂O	详情	详情
(X)	30584	N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]-N-methylamine; N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine		C₁₇H₁₅Cl₂N	详情	详情

合成路线3

A stereoselective synthesis of sertraline has been described: The silylation of 1,2-dihydronaphthalen-1(R)-ol (I) with tert-butyldiphenylsilyl chloride (TBDPS-Cl) gives the corresponding silyl ether (II), which is brominated with Br2 and triethylamine (TEA) in dichloromethane yielding the 4-bromo-compound (III). The condensation of (III) with 3,4-dichlorophenyltrimethyltin (IV), by means of a palladium catalyst affords the silylated phenylnaphthalenol (V), which is deprotected with TBAF and acetic acid to provide 4-(3,4-dichlorophenyl)-1,2-dihydronaphthalen-1(R)-ol (VI). The regioselective hydrogenation with H2 over chiral iridium or rhodium catalysts gives the (1R-trans)-tetrahydronaphthol (VII), which is treated with diphenylphosphoryl azide (DPPA) and DBU in THF yielding the (1S-cis)-azide (VIII). The reduction of (VIII) with H2 over Pd/C in ethanol affords the corresponding amine (IX), which is treated with ethyl chloroformate to give the expected carbamate (X). Finally, this compound is reduced with LiAlH(OMe)3 in THF. 2,4-Dichlorophenyltrimethyltin (IV) is prepared by reaction of 3,4-dichlorophenol (XI) with triflic anhydride in pyridine/CH2Cl2 to give triflate (XII), which is converted to (IV) by reaction with hexamethylditin and Pd(PPh3)4 in THF. The silylated naphthalenol (V) can also be obtained by condensation of (III) with the phenylboronic acid (XIII) in the presence of a palladium catalyst.

参考文献中间体

【1】 Rovis, T.; Lautens, M.; Selective functionalization of 1,2-dihydronaphthalenols leads to a concise, stereoselective synthesis of sertraline. Tetrahedron 1999, 55, 29, 8967.

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)	34037	1,2-dihydronaphthalen-1(R)-ol; (1R)-1,2-dihydro-1-naphthalenol		C₁₀H₁₀O	详情	详情
(II)	34038	tert-butyl(diphenyl)silyl (1R)-1,2-dihydro-1-naphthalenyl ether; tert-butyl[(1R)-1,2-dihydro-1-naphthalenyloxy]diphenylsilane		C₂₆H₂₈OSi	详情	详情
(III)	34039	(1R)-4-bromo-1,2-dihydro-1-naphthalenyl tert-butyl(diphenyl)silyl ether; [[(1R)-4-bromo-1,2-dihydro-1-naphthalenyl]oxy](tert-butyl)diphenylsilane		C₂₆H₂₇BrOSi	详情	详情
(IV)	34042	(3,4-dichlorophenyl)(trimethyl)stannane; 3,4-dichlorophenyltrimethyltin		C₉H₁₂Cl₂Sn	详情	详情
(V)	34041	tert-butyl(diphenyl)silyl (1R)-4-(3,4-dichlorophenyl)-1,2-dihydro-1-naphthalenyl ether; tert-butyl[[(1R)-4-(3,4-dichlorophenyl)-1,2-dihydro-1-naphthalenyl]oxy]diphenylsilane		C₃₂H₃₀Cl₂OSi	详情	详情
(VI)	34045	(1R)-4-(3,4-dichlorophenyl)-1,2-dihydro-1-naphthalenol; 4-(3,4-dichlorophenyl)-1,2-dihydronaphthalen -1(R)-o		C₁₆H₁₂Cl₂O	详情	详情
(VII)	34046	(1R,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenol		C₁₆H₁₄Cl₂O	详情	详情
(VIII)	34047	(1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenyl azide; (1S,4S)-1-azido-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalene		C₁₆H₁₃Cl₂N₃	详情	详情
(IX)	34048	(1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine; (1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenylamine		C₁₆H₁₅Cl₂N	详情	详情
(X)	34049	methyl (1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenylcarbamate		C₁₈H₁₇Cl₂NO₂	详情	详情
(XI)	34044	3,4-Dichlorophenol	95-77-2	C₆H₄Cl₂O	详情	详情
(XII)	34043	3,4-dichlorophenyl trifluoromethanesulfonate		C₇H₃Cl₂F₃O₃S	详情	详情
(XIII)	34040	3,4-Dichlorophenylboronic acid	151169-75-4	C₆H₅BCl₂O₂	详情	详情

合成路线4

A new total synthesis of sertraline has been described: The reduction of N,N-dibenzyl-D-phenylglycine methyl ester (I) with LiAlH4 in THF gives alcohol (II), which is oxidized to aldehyde (III) with oxalyl chloride in dichloromethane. The condensation of (III) with the phosphorane (IV) in benzene yields the unsaturated ester (V), which is reduced with Mg in methanol affording the saturated methyl ester (VI). Reduction of (VI) with LiAlH4 in THF provides the corresponding butanol derivative (VII), which is oxidized to the aldehyde (VIII) with pyridinium dichromate (PDC) in dichloromethane. The Grignard reaction of (VIII) with 3,4-dichlorophenylmagnesium bromide (IX) in THF affords the secondary alcohol (X), which is cyclized by means of AlCl3 in dichloromethane yielding a mixture of the desired cis-isomer (XI) along with some trans-isomer separated by column chromatography. Debenzylation of (XI) by H2 over Pd(OH)2 in methanol, followed by protection with Boc2O yields the carbamate (XII), which is methylated with methyl iodide and NaH in THF to afford the protected intermediate (XIII). Finally, compound (XIII) is deprotected with TFA in dichloromethane.

参考文献中间体

【1】 Chandrasekhar, S.; Reddy, M.V.; An expedient total synthesis of cis-(+)-sertraline from D-phenylglycine. Tetrahedron 2000, 56, 8, 1111.

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)	46527	methyl (2R)-2-(dibenzylamino)-2-phenylethanoate		C₂₃H₂₃NO₂	详情	详情
(II)	46528	(2R)-2-(dibenzylamino)-2-phenyl-1-ethanol		C₂₂H₂₃NO	详情	详情
(III)	46529	(2R)-2-(dibenzylamino)-2-phenylethanal		C₂₂H₂₁NO	详情	详情
(IV)	14182	ethyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate; (Carbethoxymethylene)triphenylphosphorane	1099-45-2	C₂₂H₂₁O₂P	详情	详情
(V)	46530	ethyl (E,4S)-4-(dibenzylamino)-4-phenyl-2-butenoate		C₂₆H₂₇NO₂	详情	详情
(VI)	46531	methyl (4S)-4-(dibenzylamino)-4-phenylbutanoate		C₂₅H₂₇NO₂	详情	详情
(VII)	46532	(4S)-4-(dibenzylamino)-4-phenyl-1-butanol		C₂₄H₂₇NO	详情	详情
(VIII)	46533	(4S)-4-(dibenzylamino)-4-phenylbutanal		C₂₄H₂₅NO	详情	详情
(IX)	10069	Bromo(3,4-dichlorophenyl)magnesium	79175-35-2	C₆H₃BrCl₂Mg	详情	详情
(X)	46534	(4S)-4-(dibenzylamino)-1-(3,4-dichlorophenyl)-4-phenyl-1-butanol		C₃₀H₂₉Cl₂NO	详情	详情
(XI)	46535	N,N-dibenzyl-N-[(1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenyl]amine; (1S,4S)-N,N-dibenzyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine		C₃₀H₂₇Cl₂N	详情	详情
(XII)	46536	tert-butyl (1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenylcarbamate		C₂₁H₂₃Cl₂NO₂	详情	详情
(XIII)	46537	tert-butyl (1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenyl(methyl)carbamate		C₂₂H₂₅Cl₂NO₂	详情	详情

合成路线5

The reaction of 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-one (I) with methylamine by means of TiCl4 in toluene gives the corresponding imine (II), which is reduced with H2 over 5% Pd/graphite, yielding a 12:1 mixture of (??(cis)(III) and (?)(trans)(III). This mixture was resolved by a treatment with (D)-mandelic acid, crystallization of the resulting salt, and treatment with NaOH in toluene/water to afford the target (+)(S,S)(cis)-sertraline.

参考文献中间体

【1】 Gershon, N.; Nidam, T.; Mendelovich, M.; Pilarsky, G. (Teva Pharmaceutical Industries Ltd.; Teva Pharmaceuticals USA, Inc.); Novel process for preparing (+)-cis-sertraline. WO 0168566 .

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)	30583	4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone; 4-(3',4'-Dichlorophenyl)-1-tetralone	79580-19-3	C₁₆H₁₂Cl₂O	详情	详情
(II)	30584	N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]-N-methylamine; N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine		C₁₇H₁₅Cl₂N	详情	详情
(III)	58591	N-[4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenyl]-N-methylamine; 4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydro-1-naphthalenamine		C₁₇H₁₇Cl₂N	详情	详情

合成路线6

The condensation of 1-naphthol (I) with an excess of o-dichlorobenzene (II) at 100 C by means of anhydrous AlCl3 gives 4-(3,4-dichlorophenyl)-1-tetralone (III), which is allowed to react with N-methylhydroxylamine (IV) and NaOAc in refluxing ethanol, yielding the nitrone (V). The reduction of (V) with H2 over RaNi in methanol affords a racemic cis/trans (9:1) mixture of methylamines, which by crystallization of its hydrochloride in ethanol provides pure (racemic)-(cis)-(VI). Finally, the target (1S)-(cis)-compound is obtained by optical resolution of (VI) with (R)-(-)-mandelic acid.

参考文献中间体

【1】 Vukics, K.; et al.; Improved industrial synthesis of antidepressant sertraline. Org Process Res Dev 2002, 6, 1, 82.

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)	22935	alpha-naphthol; 1-naphthol	90-15-3	C₁₀H₈O	详情	详情
(II)	58592	1,2-Dichlorobenzene; chloroben; chloroden; cloroben; Dichloricide; Dichlorobenzol; dilantin db; dilatin db; dizene; dowtherm e; o-Dichlorobenzene; o-Dichlorobenzol; termitkil	95-50-1	C₆H₄Cl₂	详情	详情
(III)	30583	4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone; 4-(3',4'-Dichlorophenyl)-1-tetralone	79580-19-3	C₁₆H₁₂Cl₂O	详情	详情
(IV)	12690	(Hydroxyamino)methane; N-Methylhydroxylamine	593-77-1	CH₅NO	详情	详情
(V)	58593	[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene](methyl)ammoniumolate		C₁₇H₁₅Cl₂NO	详情	详情
(VI)	58594	N-[(1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenyl]-N-methylamine; (1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydro-1-naphthalenamine		C₁₇H₁₇Cl₂N	详情	详情

合成路线7

The reaction of intermediate 4-(3,4-dichlorophenyl)-4-phenylbutyric acid (I) (see scheme number 09017202a intermediate (VII)) with (COCl)2 in dichloromethane gives the acyl chloride (II), which is condensed with methyl carbamate (III) in hot toluene to yield N-[4-(3,4-dichlorophenyl)-4-phenylbutyryl]carbamic acid methyl ester (IV). The reduction of (IV) with DIBAL in toluene/dichloromethane affords the hydroxybutyl derivative (V), which is cyclized by means of TiCl4 in dichloromethane to provide N-[4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthyl]carbamic acid methyl ester as a mixture of the cis and trans isomers, easily separated by chromatography. Finally, the desired cis isomer (VI) is reduced with LiAlH4 in THF to afford the target (rac)-sertraline.

参考文献中间体

【1】 DeNinno, M.P.; et al.; The preparation and intra- and intermolecular addition reactions of acyclic N-acylimines: Applications to the synthesis of (±)-sertraline. J Org Chem 2001, 66, 21, 6988.

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)	30581	4-(3,4-dichlorophenyl)-4-phenylbutyric acid		C₁₆H₁₄Cl₂O₂	详情	详情
(II)	30582	4-(3,4-dichlorophenyl)-4-phenylbutanoyl chloride		C₁₆H₁₃Cl₃O	详情	详情
(III)	40724	methyl carbamate; carbamic acid methyl ester	598-55-0	C₂H₅NO₂	详情	详情
(IV)	58595	methyl 4-(3,4-dichlorophenyl)-4-phenylbutanoylcarbamate		C₁₈H₁₇Cl₂NO₃	详情	详情
(V)	58596	methyl 4-(3,4-dichlorophenyl)-1-hydroxy-4-phenylbutylcarbamate		C₁₈H₁₉Cl₂NO₃	详情	详情
(VI)	34049	methyl (1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenylcarbamate		C₁₈H₁₇Cl₂NO₂	详情	详情

合成路线8

The reaction of 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-one (I) with methylamine and formic acid in DMF gives the corresponding methylimine (II), which is reduced with H2 over Pd/C to yield (rac)(cis)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine (rac)(cis)(III). Finally, this compound is submitted to optical resolution by means of mandelic acid to afford the target (1S)(cis)-sertraline.

参考文献中间体

【1】 Laitinen, I.; Pietikaeinen, P. (Orion Corporation); Process for the production of sertraline and intermediates useful therefor. US 2003013768 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(rac)-(cis)-(III)	58594	N-[(1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenyl]-N-methylamine; (1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydro-1-naphthalenamine		C₁₇H₁₇Cl₂N	详情	详情
(I)	30583	4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone; 4-(3',4'-Dichlorophenyl)-1-tetralone	79580-19-3	C₁₆H₁₂Cl₂O	详情	详情
(II)	30584	N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]-N-methylamine; N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine		C₁₇H₁₅Cl₂N	详情	详情

Extended Information