【结 构 式】 |
【分子编号】14499 【品名】2,3-Dihydrobenzofuran; 2,3-dihydro-1-benzofuran 【CA登记号】496-16-2 |
【 分 子 式 】C8H8O 【 分 子 量 】120.15092 【元素组成】C 79.97% H 6.71% O 13.32% |
合成路线1
该中间体在本合成路线中的序号:(I)The acylation of 2,3-dihydrobenzofuran (I) with acetyl chloride and AlCl3 in dichloromethane gives 5-acetyl-2,3-dihydrobenzofuran (II), which by reaction with sulfur, morpholine (III) and p-toluenesulfonic acid at high temperature yields 2-(2,3-dihydrobenzofuran-5-yl)thioacetic acid morpholide (IV). The hydrolysis of (IV) with H2SO4 in refluxing water-acetic acid affords 2-(2,3-dihydrobenzofuran-5-yl) acetic acid (V), which is esterified to (VI) with ethanol and H2SO4 in refluxing toluene. The condensation of the ester (VI) with 4-(methylthio)benzoyl chloride (VII) by means of SnCl4 in refluxing dichloromethane gives ethyl 2-[7-[4-(methylthio)benzoyl]benzofuran-5-yl]acetate (VIII), which by hydrolysis with NaOH in refluxing methanol-water yields the corresponding acid (IX). Finally, this compound is dehydrogenated with N-bromosuccinimide (NBS) and dibenzoyl peroxide in refluxing CCl4.
【1】 Dunn, J.P. [Syntex (Syntex (USA) LLC); Aroyl benzofuran and benzothiophene acetic and propionic acids, processes for their production and pharmaceutical compositions containing them. AU 8430593; EP 0132130; ES 8604554; ES 8607960; JP 85038376 . |
【2】 Prous, J.; Castaner, J.; TIFURAC SODIUM < Rec INNM; USAN >. Drugs Fut 1989, 14, 8, 775. |
【3】 Tomolonis, A.J.; Dunn, J.P.; Ackerman, N.A.; Analgetic and antiinflammatory 7-aroylbenzofuran-5-yl acetic acids and 7-aroylbenzothiophene-5-ylacetic acids. J Med Chem 1986, 29, 11, 2326. |
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) | 14499 | 2,3-Dihydrobenzofuran; 2,3-dihydro-1-benzofuran | 496-16-2 | C8H8O | 详情 | 详情 |
(II) | 21233 | 1-(2,3-dihydro-1-benzofuran-5-yl)-1-ethanone | 90843-31-5 | C10H10O2 | 详情 | 详情 |
(III) | 10388 | Morpholine | 110-91-8 | C4H9NO | 详情 | 详情 |
(IV) | 21235 | 2-(2,3-dihydro-1-benzofuran-5-yl)-1-(4-morpholinyl)-1-ethanethione | C14H17NO2S | 详情 | 详情 | |
(V) | 14500 | 2-(2,3-dihydro-1-benzofuran-5-yl)acetic acid | 69999-16-2 | C10H10O3 | 详情 | 详情 |
(VI) | 21237 | ethyl 2-(2,3-dihydro-1-benzofuran-5-yl)acetate | C12H14O3 | 详情 | 详情 | |
(VII) | 21238 | 4-(methylsulfanyl)benzoyl chloride | C8H7ClOS | 详情 | 详情 | |
(VIII) | 21239 | ethyl 2-[7-[4-(methylsulfanyl)benzoyl]-2,3-dihydro-1-benzofuran-5-yl]acetate | C20H20O4S | 详情 | 详情 | |
(IX) | 21240 | 2-[7-[4-(methylsulfanyl)benzoyl]-2,3-dihydro-1-benzofuran-5-yl]acetic acid | C18H16O4S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:(XI)Darifenacin can be obtained by three related ways: 1) The decarboxylation of (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid (I) by heating at 154 C in cyclohexanol/2-cyclohexenone gives 3(R)-hydroxypyrrolidine (II), which is N-tosylated with p-toluenesulfonyl chloride and pyridine yielding (III). The reaction of (III) with methyl p-toluenesulfonate, triphenylphosphine and diethyl azodicarboxylate (DEAD) in THF affords 1-tosyl-3(S)-(tosyloxy)pyrrolidine (IV), which is condensed with 2,2-diphenylacetonitrile (V) by means of NaH in refluxing toluene to give 2,2-diphenyl-2-[1-(p-toluenesulfonyloxy)pyrrolidin-2(S)-yl]acetonitrile (VI). Elimination of the tosyl group of (VI) with HBr and phenol in refluxing water yields 2,2-diphenyl-2-[2(S)-pyrrolidinyl]acetonitrile (VII), which by treatment with 95% H2SO4 at 100 C is converted into the corresponding acetamide (VIII). The condensation of (VIII) with 5-(chloroacetyl)-2,3-dihydrobenzofuran (IX) by means of potassium carbonate in industrial methylated spirits affords the ketonic amide (X), which is finally reduced with H2 over Pd/C in acetic acid. The intermediate 5-(chloroacetyl)-2,3-dihydrobenzofuran (IX) has been obtained by Friedel-Crafts condensation of 2,3-dihydrobenzofuran (XI) with chloroacetyl chloride by means of AlCl3 in dichloromethane. 3) The condensation of 5-(2-bromoethyl)benzofuran (XV), with the previously obtained acetamide (VIII) by means of K2CO3 in refluxing acetonitrile affords the condensation product (XVI), which is hydrogenated with H2 over Pd/C in hot acetic acid.
【1】 Graul, A.; Castaner, J.; Darifenacin. Drugs Fut 1996, 21, 11, 1105. |
【2】 Cross, P.E.; Mackenzie, A.R. (Pfizer Inc.); Pyrrolidine derivs. AU 9051402; EP 0388054; JP 1990282360; JP 1995149640; US 5096890 . |
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) | 14489 | (2S,4R)-4-hydroxytetrahydro-1H-pyrrole-2-carboxylic acid; L-Hydroxyproline | 51-35-4 | C5H9NO3 | 详情 | 详情 |
(II) | 14490 | (3R)tetrahydro-1H-pyrrol-3-ol; R-3-hydroxypyrrolidine | 2799-21-5 | C4H9NO | 详情 | 详情 |
(III) | 14491 | (3R)-1-[(4-methylphenyl)sulfonyl]tetrahydro-1H-pyrrol-3-ol | C11H15NO3S | 详情 | 详情 | |
(IV) | 14492 | (3S)-1-[(4-methylphenyl)sulfonyl]tetrahydro-1H-pyrrol-3-yl 4-methylbenzenesulfonate | C18H21NO5S2 | 详情 | 详情 | |
(V) | 14493 | alpha-phenylbenzeneacetonitrile; 2,2-diphenylacetonitrile; Diphenylacetonitrile | 86-29-3 | C14H11N | 详情 | 详情 |
(VI) | 14494 | 2-[(3S)-1-[(4-methylphenyl)sulfonyl]tetrahydro-1H-pyrrol-3-yl]-2,2-diphenylacetonitrile | C25H24N2O2S | 详情 | 详情 | |
(VII) | 14495 | 2,2-diphenyl-2-[(3S)tetrahydro-1H-pyrrol-3-yl]acetonitrile | C18H18N2 | 详情 | 详情 | |
(VIII) | 14496 | 2,2-diphenyl-2-[(3S)tetrahydro-1H-pyrrol-3-yl]acetamide | C18H20N2O | 详情 | 详情 | |
(IX) | 14497 | 2-chloro-1-(2,3-dihydro-1-benzofuran-5-yl)-1-ethanone | C10H9ClO2 | 详情 | 详情 | |
(X) | 14498 | 2-[(3S)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)-2-oxoethyl]tetrahydro-1H-pyrrol-3-yl]-2,2-diphenylacetamide | C28H28N2O3 | 详情 | 详情 | |
(XI) | 14499 | 2,3-Dihydrobenzofuran; 2,3-dihydro-1-benzofuran | 496-16-2 | C8H8O | 详情 | 详情 |
(XII) | 14500 | 2-(2,3-dihydro-1-benzofuran-5-yl)acetic acid | 69999-16-2 | C10H10O3 | 详情 | 详情 |
(XIII) | 14501 | 2-(2,3-dihydro-1-benzofuran-5-yl)-1-ethanol | C10H12O2 | 详情 | 详情 | |
(XIV) | 14502 | 5-(2-bromoethyl)-2,3-dihydro-1-benzofuran | C10H11BrO | 详情 | 详情 | |
(XV) | 14503 | 5-(2-bromoethyl)-1-benzofuran | C10H9BrO | 详情 | 详情 | |
(XVI) | 14504 | 2-[(3S)-1-[2-(1-benzofuran-5-yl)ethyl]tetrahydro-1H-pyrrol-3-yl]-2,2-diphenylacetamide | C28H28N2O2 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号:(I)Electrophilic sulfonation of 2,3-dihydrobenzofuran (I) using sulfur trioxide-dimethylformamide complex produced sulfonic acid (II), which was subsequently converted into the sulfonyl chloride (III) by chlorination with SOCl2. Reaction of sulfonyl chloride (III) with a solution of ammonia in cold dichloroethane gave rise to the sulfonamide (IV). This was subsequently condensed with 3,4-dichlophenyl isocyanate (V) to furnish the target sulfonyl urea
【1】 Tao, E.V.-P.; Miller, W.D. (Eli Lilly and Company); Synthesis of bicyclic aromatic sulfonic acids, sulfonyl chlorides and sulfonamides. EP 0583960 . |
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) | 14499 | 2,3-Dihydrobenzofuran; 2,3-dihydro-1-benzofuran | 496-16-2 | C8H8O | 详情 | 详情 |
(II) | 59847 | 2,3-dihydro-1-benzofuran-5-sulfonic acid | C8H8O4S | 详情 | 详情 | |
(III) | 59848 | 2,3-dihydro-1-benzofuran-5-sulfonyl chloride | C8H7ClO3S | 详情 | 详情 | |
(IV) | 59849 | 2,3-dihydro-1-benzofuran-5-sulfonamide | C8H9NO3S | 详情 | 详情 | |
(V) | 34282 | 1,2-dichloro-4-isocyanatobenzene; 3,4-dichlorophenyl isocyanate | 102-36-3 | C7H3Cl2NO | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号:(I)The reaction of 2,3-dihydrobenzofuran (I) with dichloromethyl methyl ether (II) by means of TiCl4 in dichloromethane gives 2,3-dihydrobenzofuran-5-carbaldehyde (III), which is condensed with the phosphonate (IV) by means of NaH in THF to yield the propenoic ester (V). The reduction of (V) with H2 over Pd/C in ethanol affords the saturated propionic ester (VI), which is brominated with Br2 in HOAc providing the 7-bromo derivative (VII). Further bromination of (VII) with Br2 and Fe in HOAc gives the 6,7-dibromo derivative (VIII), which is hydrolyzed with NaOH in THF/water to yield the propionic acid derivative (IX). The reaction of (IX) with hot SOCl2 affords the corresponding acyl chloride (X), which is cyclized by means of AlCl3 in dichloroethane to provide 4,5-dibromo-2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-one (XI). The debromination of (XI) by means of H2 over Pd/C in Ac-OH gives 2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-one (XII), which is condensed with the phosphorane (XIII) by means of NaH in THF to yield 2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-ylidene)acetonitrile (XIV). The selective reduction of the cyano group of (XIV) by means of H2 over Raney cobalt in ethanol/NH3 affords 2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-ylidene)ethylamine (XV), which is condensed with propionyl chloride (XVI) by means of TEA in THF to provide the propionamide (XVII). Finally this compound is enantioselectively reduced with H2 over a chiral Ru catalyst (Ru(OAc)2-(S)-BINAP) in methanol to give rise to the target (S)-enantiomer. Alternatively, the reduction of 2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-ylidene)acetonitrile (XIV) with H2 over RaNi in ethanol/NH3 gives 2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)ethylamine (XVIII), which is acylated with propionyl chloride (XVI) and TEA in DMF to yield the racemic propionamide (XIX). Finally this compound is submitted to optical resolution by means of chiral HPLC to afford the target (S)-enantiomer.
【1】 Chilman-Blair, K.; Castaner, J.; Silvestre, J.S.; Bayes, M.; TAK-375. Drugs Fut 2003, 28, 10, 950. |
【2】 Ohkawa, S.; Uchikawa, O.; Fukatsu, K.; Miyamoto, M. (Takeda Chemical Industries, Ltd.); Tricyclic cpds., their production and use. EP 0885210; JP 1998287665; JP 1999152281; WO 9732871 . |
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) | 14499 | 2,3-Dihydrobenzofuran; 2,3-dihydro-1-benzofuran | 496-16-2 | C8H8O | 详情 | 详情 |
(II) | 40668 | dichloro(methoxy)methane; dichloromethyl methyl ether | 4885-02-3 | C2H4Cl2O | 详情 | 详情 |
(III) | 52198 | 2,3-Dihydrobenzo[b]furan-5-carboxaldehyde | C9H8O2 | 详情 | 详情 | |
(IV) | 10019 | Ethyl 2-(diethoxyphosphoryl)acetate; Triethyl phosphonoacetate | 867-13-0 | C8H17O5P | 详情 | 详情 |
(V) | 57393 | ethyl (E)-3-(2,3-dihydro-1-benzofuran-5-yl)-2-propenoate | C13H14O3 | 详情 | 详情 | |
(VI) | 57394 | ethyl 3-(2,3-dihydro-1-benzofuran-5-yl)propanoate | C13H16O3 | 详情 | 详情 | |
(VII) | 57395 | ethyl 3-(7-bromo-2,3-dihydro-1-benzofuran-5-yl)propanoate | C13H15BrO3 | 详情 | 详情 | |
(VIII) | 57396 | ethyl 3-(6,7-dibromo-2,3-dihydro-1-benzofuran-5-yl)propanoate | C13H14Br2O3 | 详情 | 详情 | |
(IX) | 57397 | 3-(6,7-dibromo-2,3-dihydro-1-benzofuran-5-yl)propanoic acid | C11H10Br2O3 | 详情 | 详情 | |
(X) | 57398 | 3-(6,7-dibromo-2,3-dihydro-1-benzofuran-5-yl)propanoyl chloride | C11H9Br2ClO2 | 详情 | 详情 | |
(XI) | 57399 | 4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one | C11H8Br2O2 | 详情 | 详情 | |
(XII) | 57400 | 1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one | C11H10O2 | 详情 | 详情 | |
(XIII) | 10045 | Diethyl cyanomethylphosphonate | 2537-48-6 | C6H12NO3P | 详情 | 详情 |
(XIV) | 57401 | 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetonitrile | C13H11NO | 详情 | 详情 | |
(XV) | 57402 | 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)-1-ethanamine; 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)ethylamine | C13H15NO | 详情 | 详情 | |
(XVI) | 15967 | propanoyl chloride; propionyl chloride | 79-03-8 | C3H5ClO | 详情 | 详情 |
(XVII) | 57403 | N-[2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)ethyl]propanamide | C16H19NO2 | 详情 | 详情 | |
(XVIII) | 57404 | 2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)-1-ethanamine; 2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine | C13H17NO | 详情 | 详情 | |
(XIX) | 57405 | N-[2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]propanamide | C16H21NO2 | 详情 | 详情 |
合成路线5
该中间体在本合成路线中的序号:(I)The reaction of 2,3-dihydrobenzofuran (I) with DMF (II) and POCl3 gives 2,3-dihydrobenzofuran-5-carbaldehyde (III), which is condensed with the phosphonate (IV) by means of t-BuONa in toluene to yield the acrylate (V). The reduction of (V) with H2 over Pd/C in AcOH affords the corresponding propionate (VI), which is brominated with Br2 in AcOH to provide the dibromo derivative (VII). The hydrolysis of the ester group of (VII) in acidic medium gives the expected propionic acid derivative (VIII), which is treated with SOCl2 in dichloromethane to yield the propionyl chloride (IX). The cyclization of (IX) by means of AlCl3 in dichloromethane affords the 4,5-dibromo-2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-one (X), which is submitted to an hydrogenolytic debromination with H2 over Pd/C in methanol to provide the 2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-one (XI). The Wittig condensation of (XI) with phosphonate (XII) by means of NaOMe in toluene gives 2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-ylidene)acetonitrile (XIII), which is reduced with H2 and Raney-Co in toluene/MeOH to yield 2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-ylidene)ethylamine (XIV). The asymmetric reduction of (XIV) with H2 and a chiral Ru catalyst in toluene/MeOH affords the 2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8(S)-yl)ethylamine (XV), which is finally acylated with propionyl chloride (XVI) and NaOH in aq. THF to provide the target chiral propionamide.
【1】 Ohkawa, S.; Discovery of the novel melatonin agonist TAK-375. 22nd Symp Med Chem (Nov 27 2002, Shizuoka) 2002, Abst IL 11. |
【2】 Chilman-Blair, K.; Castaner, J.; Silvestre, J.S.; Bayes, M.; TAK-375. Drugs Fut 2003, 28, 10, 950. |
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) | 14499 | 2,3-Dihydrobenzofuran; 2,3-dihydro-1-benzofuran | 496-16-2 | C8H8O | 详情 | 详情 |
(II) | 45439 | dimethylformamide | C3H7NO | 详情 | 详情 | |
(III) | 52198 | 2,3-Dihydrobenzo[b]furan-5-carboxaldehyde | C9H8O2 | 详情 | 详情 | |
(IV) | 10019 | Ethyl 2-(diethoxyphosphoryl)acetate; Triethyl phosphonoacetate | 867-13-0 | C8H17O5P | 详情 | 详情 |
(V) | 57393 | ethyl (E)-3-(2,3-dihydro-1-benzofuran-5-yl)-2-propenoate | C13H14O3 | 详情 | 详情 | |
(VI) | 57394 | ethyl 3-(2,3-dihydro-1-benzofuran-5-yl)propanoate | C13H16O3 | 详情 | 详情 | |
(VII) | 57396 | ethyl 3-(6,7-dibromo-2,3-dihydro-1-benzofuran-5-yl)propanoate | C13H14Br2O3 | 详情 | 详情 | |
(VIII) | 57397 | 3-(6,7-dibromo-2,3-dihydro-1-benzofuran-5-yl)propanoic acid | C11H10Br2O3 | 详情 | 详情 | |
(IX) | 57398 | 3-(6,7-dibromo-2,3-dihydro-1-benzofuran-5-yl)propanoyl chloride | C11H9Br2ClO2 | 详情 | 详情 | |
(X) | 57399 | 4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one | C11H8Br2O2 | 详情 | 详情 | |
(XI) | 57400 | 1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one | C11H10O2 | 详情 | 详情 | |
(XII) | 10045 | Diethyl cyanomethylphosphonate | 2537-48-6 | C6H12NO3P | 详情 | 详情 |
(XIII) | 57401 | 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetonitrile | C13H11NO | 详情 | 详情 | |
(XIV) | 57402 | 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)-1-ethanamine; 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)ethylamine | C13H15NO | 详情 | 详情 | |
(XV) | 62217 | 2-[(8S)-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]-1-ethanamine; 2-[(8S)-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethylamine | C13H17NO | 详情 | 详情 | |
(XVI) | 15967 | propanoyl chloride; propionyl chloride | 79-03-8 | C3H5ClO | 详情 | 详情 |
合成路线6
该中间体在本合成路线中的序号:(II)
【1】 Urayruna S. Mutou E, Inagaki A, et aL. 2006. Preparation of (S)-2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-yl) ethylamine derivative by asymmetric hydrogenation of 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b] furan-8-ylidene) ethylamine. W0 2006030739(本专利属于Takeda Pharmaceutical company Limited, Japan) |
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) | 45439 | dimethylformamide | C3H7NO | 详情 | 详情 | |
(II) | 14499 | 2,3-Dihydrobenzofuran; 2,3-dihydro-1-benzofuran | 496-16-2 | C8H8O | 详情 | 详情 |
(III) | 52198 | 2,3-Dihydrobenzo[b]furan-5-carboxaldehyde | C9H8O2 | 详情 | 详情 | |
(IV) | 57393 | ethyl (E)-3-(2,3-dihydro-1-benzofuran-5-yl)-2-propenoate | C13H14O3 | 详情 | 详情 | |
(V) | 57394 | ethyl 3-(2,3-dihydro-1-benzofuran-5-yl)propanoate | C13H16O3 | 详情 | 详情 | |
(VI) | 57396 | ethyl 3-(6,7-dibromo-2,3-dihydro-1-benzofuran-5-yl)propanoate | C13H14Br2O3 | 详情 | 详情 | |
(VII) | 57399 | 4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one | C11H8Br2O2 | 详情 | 详情 | |
(VIII) | 57400 | 1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one | C11H10O2 | 详情 | 详情 | |
(IX) | 57401 | 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetonitrile | C13H11NO | 详情 | 详情 | |
(X) | 57402 | 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)-1-ethanamine; 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)ethylamine | C13H15NO | 详情 | 详情 | |
(XI) | 62217 | 2-[(8S)-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]-1-ethanamine; 2-[(8S)-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethylamine | C13H17NO | 详情 | 详情 |