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【结 构 式】 
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【分子编号】26253 【品名】2-cyclohexen-1-one；Cyclohex-2-enone；2-cyclohexenone 【CA登记号】930-68-7 |
【 分 子 式 】C6H8O 【 分 子 量 】96.12892 【元素组成】C 74.97% H 8.39% O 16.64% |
合成路线1
该中间体在本合成路线中的序号：(I)The condensation of cyclohexenone (I) with diethyl alpha-methylmalonate (II) by means of sodium ethoxide in ethanol gives diethyl alpha-methyl-3-oxocyclohexanemalonate (III), oil b.p.(0.8) = 149-52 C, n(20)(D) = 1.4660, which is hydrolyzed and decarboxylated with refluxing dioxane-HCl to yield alpha-methyl-3-oxocyclohexaneacetic acid (IV), oil, b.p.(0.7) = 164-6 C, n(20)(D) = 1.4794. The condensation of (IV) with 4-chlorophenylhydrazine (A) in acetic acid-water atfords 6-chloro-alpha-methyl-1,2,3,4-tetrahydrocarbazole-2-acetic acid (V), m.p. 193-202 C, which is esterified with ethanol-HCl to ethyl 6-chloro-alpha-methyl-1,2,3,4-tetrahydrocarbazole-2-acetate (VI) and aromatized with chloranil (B) in refluxing xylene to give ethyl 6-chloro-alpha-methylcarbazole-2-acetate (VII), m.p. 106.0-7.5 C. Finally, this ester is hydrolyzed with NaOH in refluxing ethanol.
| 【1】 Berger, L.; Corraz, A.J.; Carbazoles. ES 417167; ES 442684; ES 442685; US 3896145 . |
| 【2】 Weetman, D.F.; Castaner, J.; Carprofen. Drugs Fut 1977, 2, 1, 15. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (B) | 21891 | 2,3,5,6-Tetrachloro-1,4-benzoquinone; 2,3,5,6-Tetrachlorobenzo-1,4-quinone; p-Chloranil | 118-75-2 | C6Cl4O2 | 详情 | 详情 |
| (A) | 33345 | 1-(4-chlorophenyl)hydrazine; 4-Chlorophenylhydrazine | 1073-70-7 | C6H7ClN2 | 详情 | 详情 |
| (I) | 26253 | 2-cyclohexen-1-one；Cyclohex-2-enone；2-cyclohexenone | 930-68-7 | C6H8O | 详情 | 详情 |
| (II) | 30310 | diethyl 2-methylmalonate | 609-08-5 | C8H14O4 | 详情 | 详情 |
| (III) | 33625 | diethyl 2-methyl-2-(3-oxocyclohexyl)malonate | C14H22O5 | 详情 | 详情 | |
| (IV) | 33626 | 2-(3-oxocyclohexyl)propionic acid | C9H14O3 | 详情 | 详情 | |
| (V) | 33627 | 2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)propionic acid | C15H16ClNO2 | 详情 | 详情 | |
| (VI) | 33628 | ethyl 2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)propanoate | C17H20ClNO2 | 详情 | 详情 | |
| (VII) | 33629 | ethyl 2-(6-chloro-9H-carbazol-2-yl)propanoate | C17H16ClNO2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XXI)Treatment of 2-cyclohexenone (XXI) with SO2Cl2 and 2,6-lutidine in dichloromethane provides 2-chloro-2-cyclohexenone (XXII), which is reduced with (S)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]-oxazaborole and borane dimethyl sulfide complex in THF/MeOH giving (R)-2-chloro-2-cyclohexen-1-ol (XXIII). Reaction of (XXIII) with trichloroacetonitrile by means of NaH in diethyl ether gives the cyclohexenol derivative (XXIV), which is converted into acetamide (XXV) by heating at 140 C in chlorobenzene. Hydrolysis of (XXV) with K2CO3 in water/methanol affords (S)-2-chloro-2-cyclohexen-1-amine (XXVI), which is then condensed with N-phthaloyl-L-phenylalanine acid chloride (VI) in ethyl acetate to yield amide (XXVII). Finally, ozonolysis of amide (XXVII) in CH2Cl2/MeOH, followed by reduction with tributylphosphine and treatment with TFA in refluxing CH2Cl2 provides the previously described intermediate (XII).
| 【1】 del Fresno, M.; Bayes, M.; Castaner, R.M.; Sorbera, L.A.; MDL-100240. Drugs Fut 2002, 27, 5, 458. |
| 【2】 Flynn, G.A. (Merrell Pharmaceuticals, Inc.); Novel process for preparing (S)-1-[2(S)-(1,3-dihydro-1,3-dioxo-isoindo-2-yl)-1-oxo-3-phenylpropyl]-1,2,3,4-tetrahydro-2-pyridine-carboxylic acid methyl ester and intermediates thereof. WO 9514663 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 28292 | (S)-Methyl oxazaborolidine; (3aS)-1-methyl-3,3-diphenyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole | 112022-81-8 | C18H20BNO | 详情 | 详情 | |
| (VI) | 52756 | (2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropanoyl chloride | C17H12ClNO3 | 详情 | 详情 | |
| (XII) | 37296 | methyl (2S)-1-[(2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropanoyl]-1,2,3,4-tetrahydro-2-pyridinecarboxylate | C24H22N2O5 | 详情 | 详情 | |
| (XXI) | 26253 | 2-cyclohexen-1-one；Cyclohex-2-enone；2-cyclohexenone | 930-68-7 | C6H8O | 详情 | 详情 |
| (XXII) | 53409 | 2-chloro-2-cyclohexen-1-one | n/a | C6H7ClO | 详情 | 详情 |
| (XXIII) | 53410 | (1R)-2-chloro-2-cyclohexen-1-ol | n/a | C6H9ClO | 详情 | 详情 |
| (XXIV) | 53411 | (1R)-2-chloro-2-cyclohexen-1-yl 2,2,2-trichloroethanimidoate | n/a | C8H9Cl4NO | 详情 | 详情 |
| (XXV) | 53412 | 2,2,2-trichloro-N-[(1S)-2-chloro-2-cyclohexen-1-yl]acetamide | n/a | C8H9Cl4NO | 详情 | 详情 |
| (XXVI) | 53413 | (1S)-2-chloro-3-cyclohexen-1-amine; (1S)-2-chloro-3-cyclohexen-1-ylamine | n/a | C6H10ClN | 详情 | 详情 |
| (XXVII) | 53414 | (2S)-N-[(1S)-2-chloro-3-cyclohexen-1-yl]-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropanamide | n/a | C23H21ClN2O3 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(I)The asymetric Michael addition of malonic ester (II) to 2-cyclohexenone (I) catalyzed by (R)-ALB and t-BuOK in THF gives the (R)-enantiomer (III), which is cyclized with phenylhydrazine (IV) in hot acetic acid yielding the tetrahydrocarbazole (V). The protection of (V) with Boc2O, TEA and DMAP in dichloromethane gives protected (VI), which is condensed with acetaldehyde (VII) by means of LDA in THF affording crotonate (VIII). The reduction of the ester group of (VIII) with DIBAL, followed by oxidation with MnO2 gives the corresponding aldehyde (IX), which is reductocondensed with 2-aminoacetaldehyde dimethylacetal (XI) by means of titanium tetraisopropoxide and NaBH4 in toluene/methanol providing adduct (XI). The deprotection of (XI) with TFA and anisole gives the free tetrahydrocarbazole (XII), which is cyclized by means of DDQ in THF yielding the tetracyclic compound (XIII). The reduction of the exocyclic double bond of (XIII) with RhCl(PPh3)3 in benzene/isopropanol affords the (S)-ethyl derivative (XIV), which is treated with Et-SH and BF3/Et2O in dichloromethane to give the thioacetal (XV). Finally, this compound is cyclized with DMTSF, LiAlH4 and Raney-Ni in refluxing ethanol.
| 【1】 Shimizu, S.; et al.; Catalytic asymmetric synthesis of tubifolidine. J Org Chem 1998, 63, 21, 7547. |
| 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) | 26253 | 2-cyclohexen-1-one；Cyclohex-2-enone；2-cyclohexenone | 930-68-7 | C6H8O | 详情 | 详情 |
| (II) | 19373 | dimethyl malonate；Methyl malonate;Propanedioic acid dimethyl ester | 108-59-8 | C5H8O4 | 详情 | 详情 |
| (III) | 37225 | dimethyl 2-[(1R)-3-oxocyclohexyl]malonate | C11H16O5 | 详情 | 详情 | |
| (IV) | 11818 | Phenyl hydrazine; 1-Phenylhydrazine | 100-63-0 | C6H8N2 | 详情 | 详情 |
| (V) | 37226 | methyl 2-[(2R)-2,3,4,9-tetrahydro-1H-carbazol-2-yl]acetate | C15H17NO2 | 详情 | 详情 | |
| (VI) | 37227 | tert-butyl (2R)-2-(2-methoxy-2-oxoethyl)-1,2,3,4-tetrahydro-9H-carbazole-9-carboxylate | C20H25NO4 | 详情 | 详情 | |
| (VII) | 11974 | Acetaldehyde | 75-07-0 | C2H4O | 详情 | 详情 |
| (VIII) | 37228 | tert-butyl (2R)-2-[(E)-1-(methoxycarbonyl)-1-propenyl]-1,2,3,4-tetrahydro-9H-carbazole-9-carboxylate | C22H27NO4 | 详情 | 详情 | |
| (IX) | 37229 | tert-butyl (2R)-2-[(E)-1-formyl-1-propenyl]-1,2,3,4-tetrahydro-9H-carbazole-9-carboxylate | C21H25NO3 | 详情 | 详情 | |
| (X) | 37158 | ethyl 5-[3-(benzyloxy)-2-formylphenoxy]pentanoate | C21H24O5 | 详情 | 详情 | |
| (XI) | 37230 | tert-butyl (2R)-2-((E)-1-[[(2,2-dimethoxyethyl)amino]methyl]-1-propenyl)-1,2,3,4-tetrahydro-9H-carbazole-9-carboxylate | C25H36N2O4 | 详情 | 详情 | |
| (XII) | 37231 | (E)-N-(2,2-dimethoxyethyl)-2-[(2R)-2,3,4,9-tetrahydro-1H-carbazol-2-yl]-2-buten-1-amine; N-(2,2-dimethoxyethyl)-N-[(E)-2-[(2R)-2,3,4,9-tetrahydro-1H-carbazol-2-yl]-2-butenyl]amine | C20H28N2O2 | 详情 | 详情 | |
| (XIII) | 37232 | 2-[(1S,12R)-13-[(E)ethylidene]-9,15-diazatetracyclo[10.3.1.0(2,10).0(3,8)]hexadeca-2(10),3,5,7-tetraen-15-yl]-1-methoxyethyl methyl ether; (1S,12R)-15-(2,2-dimethoxyethyl)-13-[(E)ethylidene]-9,15-diazatetracyclo[10.3.1.0(2,10).0(3,8)]hexadeca-2(10),3,5,7-tetraene | C20H26N2O2 | 详情 | 详情 | |
| (XIV) | 37233 | 2-[(1S,12R,13S)-13-ethyl-9,15-diazatetracyclo[10.3.1.0(2,10).0(3,8)]hexadeca-2(10),3,5,7-tetraen-15-yl]-1-methoxyethyl methyl ether; (1S,12R,13S)-15-(2,2-dimethoxyethyl)-13-ethyl-9,15-diazatetracyclo[10.3.1.0(2,10).0(3,8)]hexadeca-2(10),3,5,7-tetraene | C20H28N2O2 | 详情 | 详情 | |
| (XV) | 37234 | ethyl 2-[(1S,12R,13S)-13-ethyl-9,15-diazatetracyclo[10.3.1.0(2,10).0(3,8)]hexadeca-2(10),3,5,7-tetraen-15-yl]-1-(ethylsulfanyl)ethyl sulfide; (1S,12R,13S)-15-[2,2-bis(ethylsulfanyl)ethyl]-13-ethyl-9,15-diazatetracyclo[10.3.1.0(2,10).0(3,8)]hexadeca-2(10),3,5,7-tetraene | C22H32N2S2 | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(I)Michael addition of 4-(phenylsulfanyl)thiophenol (II) to cyclohexenone (I) afforded the ketosulfide (III). This was reduced with NaBH4 to give a diastereomeric mixture of alcohols (IV). Subsequent oxidation of sulfide group of (IV) with Oxone provided sulfone (V). Condensation with potassium thioacetate under Mitsunobu conditions gave the corresponding thioester as a mixture of isomers, from which the major trans isomer (VI) was isolated by chromatography. Finally, deprotection of (VI) with sodium methoxide in MeOH yielded the target thiol.
| 【1】 Mischke, B.V.; Freskos, J.N.; Stevens, A.M.; Mullins, P.B.; McDonald, J.J.; Stegeman, R.A.; Shieh, H.-S.; Synthesis and identification of conformationally constrained selective MMP inhibitors. Bioorg Med Chem Lett 1999, 9, 13, 1757. |
| 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) | 26253 | 2-cyclohexen-1-one；Cyclohex-2-enone；2-cyclohexenone | 930-68-7 | C6H8O | 详情 | 详情 |
| (II) | 26259 | 4-(phenylsulfanyl)phenylhydrosulfide | C12H10S2 | 详情 | 详情 | |
| (III) | 26260 | 3-[[4-(phenylsulfanyl)phenyl]sulfanyl]cyclohexanone | C18H18OS2 | 详情 | 详情 | |
| (IV) | 26261 | 3-[[4-(phenylsulfanyl)phenyl]sulfanyl]cyclohexanol | C18H20OS2 | 详情 | 详情 | |
| (V) | 26262 | 3-[[4-(phenylsulfanyl)phenyl]sulfonyl]cyclohexanol | C18H20O3S2 | 详情 | 详情 | |
| (VI) | 26263 | S-((1S,3S)-3-[[4-(phenylsulfanyl)phenyl]sulfonyl]cyclohexyl) ethanethioate | C20H22O3S3 | 详情 | 详情 |
合成路线5
该中间体在本合成路线中的序号：(I)Michael addition of 4-(phenoxy)thiophenol (II) to cyclohexenone (I) afforded the ketosulfide (III). This was reduced with NaBH4 to give a diastereomeric mixture of alcohols (IV). Subsequent oxidation of sulfide group of (IV) with Oxone provided sulfone (V). Condensation with potassium thioacetate under Mitsunobu conditions gave the corresponding thioester as a mixture of isomers, from which the major trans isomer (VI) was isolated by chromatography. Finally, deprotection of (VI) with sodium methoxide in MeOH yielded the target thiol.
| 【1】 Mischke, B.V.; Freskos, J.N.; Stevens, A.M.; Mullins, P.B.; McDonald, J.J.; Stegeman, R.A.; Shieh, H.-S.; Synthesis and identification of conformationally constrained selective MMP inhibitors. Bioorg Med Chem Lett 1999, 9, 13, 1757. |
| 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) | 26253 | 2-cyclohexen-1-one；Cyclohex-2-enone；2-cyclohexenone | 930-68-7 | C6H8O | 详情 | 详情 |
| (II) | 26254 | 4-phenoxybenzenethiol; 4-phenoxyphenylhydrosulfide | C12H10OS | 详情 | 详情 | |
| (III) | 26255 | 3-[(4-phenoxyphenyl)sulfanyl]cyclohexanone | C18H18O2S | 详情 | 详情 | |
| (IV) | 26256 | 3-[(4-phenoxyphenyl)sulfanyl]cyclohexanol | C18H20O2S | 详情 | 详情 | |
| (V) | 26257 | 3-[(4-phenoxyphenyl)sulfonyl]cyclohexanol | C18H20O4S | 详情 | 详情 | |
| (VI) | 26258 | S-[(1S,3S)-3-[(4-phenoxyphenyl)sulfonyl]cyclohexyl] ethanethioate | C20H22O4S2 | 详情 | 详情 |
合成路线6
该中间体在本合成路线中的序号：(IV)(4-Chlorophenyl)acetonitrile (I) is reduced with DIBAL to the aldehyde (II), which is subsequently converted to enamine (III) by treatment with dimethylamine in the presence of CaCl2 as the dehydrating agent. Condensation of enamine (III) with 2-cyclohexenone (IV) produces a mixture of the trans endo/exo substituted bicycloalkanones (V) and (VI), separable by column chromatography. Reduction of the endo isomer (V) with NaBH4 yields the bicyclic amino alcohol as a diastereomeric mixture. After chromatographic isolation, the desired isomer is esterified with benzoyl chloride to furnish the corresponding amino ester, which is finally converted to the title hydrochloride salt.
| 【1】 Coons, S.; et al.; Synthesis and pharmacology of potential site-specific cocaine abuse treatment agents: The role of the phenyl group in 2-substituted-6-aminobicyclo[2.2.2]octanes. Med Chem Res 2002, 11, 1, 24. |
| 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) | 57732 | (1S,2R,4S,5R,6R)-5-(4-chlorophenyl)-6-(dimethylamino)bicyclo[2.2.2]octan-2-ol | C16H22ClNO | 详情 | 详情 | |
| (VIIb) | 57733 | (1S,2S,4S,5R,6R)-5-(4-chlorophenyl)-6-(dimethylamino)bicyclo[2.2.2]octan-2-ol | C16H22ClNO | 详情 | 详情 | |
| (I) | 22871 | 2-(4-chlorophenyl)acetonitrile | 140-53-4 | C8H6ClN | 详情 | 详情 |
| (II) | 57728 | 2-(4-chlorophenyl)acetaldehyde | C8H7ClO | 详情 | 详情 | |
| (III) | 57729 | (E)-2-(4-chlorophenyl)-N,N-dimethyl-1-ethenamine; N-[(E)-2-(4-chlorophenyl)ethenyl]-N,N-dimethylamine | C10H12ClN | 详情 | 详情 | |
| (IV) | 26253 | 2-cyclohexen-1-one；Cyclohex-2-enone；2-cyclohexenone | 930-68-7 | C6H8O | 详情 | 详情 |
| (V) | 57730 | (1S,4S,5R,6R)-5-(4-chlorophenyl)-6-(dimethylamino)bicyclo[2.2.2]octan-2-one | C16H20ClNO | 详情 | 详情 | |
| (VI) | 57731 | (1S,4S,5S,6S)-5-(4-chlorophenyl)-6-(dimethylamino)bicyclo[2.2.2]octan-2-one | C16H20ClNO | 详情 | 详情 |
合成路线7
该中间体在本合成路线中的序号：(XII)Protection of 1,5,6,7-tetrahydroindol-4-one (I) with Boc2O by means of t-BuOK in refluxing THF gives the corresponding N-Boc-indolone (II), which is then reduced with H2 over Pt/C in MeOH to yield (3aR*, 4S*,7aR*)-cis-N-Boc-4-hydroxyoctahydroindole (III). Swern oxidation of alcohol (III) using (COCl)2, DMSO and Et3N in THF affords the racemic perhydroindolone (IV), which is resolved using chiral chromatography to the (3aR,7aR)-enantiomer (V). Alternatively, enantioselective acetylation of racemic alcohol (III) with vinyl acetate in the presence of immobilized Candida antarctica lipase (Novozyme 435), followed by flash chromatographic separation of the undesired (3aS,4R,7aS)-acetate provides unreacted (3aR,4S,7aR)-alcohol (VI), which is then oxidized to ketone (V) under Swern conditions. Treatment of 1-ethynyl-3-methylbenzene (VII) with BuLi in THF at –20 °C and subsequent enantioselective condensation with ketone (V) leads to propargylic alcohol (VIII), which is then N-deprotected with HCl in EtOAc to produce the amine (IX). Finally, amine (IX) is acylated with methyl chloroformate (X) in the presence of Et3N in CH2Cl2 .
Alternatively, Michael addition of aziridine (XI) to 2-cyclohexenone (XII) in toluene gives 3-(1-aziridinyl)cyclohexanone (XIII), which is submitted to aziridine ring opening by treatment with methyl chloroformate in toluene to provide methyl N-2-chloroethyl-N-(3-oxocyclohexyl)carba-mate (XIV). Intramolecular cyclization of carbamate (XIV) in the presence of pyrrolidine and Et3N in CH2Cl2 affords racemic methyl 4-oxooctahydroindole-1-carboxylate (XV), which is then subjected to chiral chromatographic separation, resulting in the (3aR,7aR)-enantiomer (XVI). Finally, 1-ethynyl-3-methylbenzene (VII) is stereospecifically added to ketone (XVI) in the presence of n-Hex-Li in THF .
| 【1】 Auberson, Y., Ofner, S., Gasparini, F. (Novartis AG; Novartis Pharma GmbH). Acetylene derivatives having mGluR5 antagonistic activity. EP 1453512, JP 2005514381, JP 200830326, US 200506591, US 7348353, US 2008146647, US 2008303226, WO 2003047581. |
| 【2】 Kuesters, E., Acemoglu, M., Lustenberger, P., Sedelmeier, G., Schmidt, B.,Penn, G. (Novartis AG). Processes for the preparation of 4-oxo-octahydroindole-1-carbocylic acid methyl ester and derivatives thereof. CN 102119151, EP 2315748, JP 2011530566, KR 2011042222, US 2011144352, US 8084487, WO 2010018154. |
| 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) | 68376 | 6,7-dihydro-1H-indol-4(5H)-one;1,5,6,7-tetrahydro-4h-indol-4-one;4-0xo-4,5,6,7-tetrahydroindole;4-Oxo-1,5,6,7-tetrahydroindole | 13754-86-4 | C8H9NO | 详情 | 详情 |
| (II) | 68377 | tert-butyl 4-oxo-4,5,6,7-tetrahydro-1H-indole-1-carboxylate | C13H17NO3 | 详情 | 详情 | |
| (III) | 68378 | racemic N-Boc-4-hydroxyoctahydroindole;racemic tert-butyl 4-hydroxyoctahydro-1H-indole-1-carboxylate | C13H23NO3 | 详情 | 详情 | |
| (IV) | 68379 | racemic tert-butyl 4-oxooctahydro-1H-indole-1-carboxylate | C13H21NO3 | 详情 | 详情 | |
| (V) | 68380 | (3aR,7aR)-tert-butyl 4-oxooctahydro- 1H-indole-1-carboxylate | C13H21NO3 | 详情 | 详情 | |
| (VI) | 68381 | (3aR,4S,7aR)-cis-N-Boc-4- hydroxyoctahydroindole;(3aR,4S,7aR)-tert-butyl 4- hydroxyoctahydro-1H-indole-1-carboxylate | C13H23NO3 | 详情 | 详情 | |
| (VII) | 68382 | 1-ethynyl-3-methylbenzene;3-Ethynyltoluene;3-Methylphenylacetylene;3'-Methylphenylacetylene | 766-82-5 | C9H8 | 详情 | 详情 |
| (VIII) | 68384 | (3aR,4S,7aR)-tert-butyl 4-hydroxy-4-(m-tolylethynyl)octahydro-1H-indole-1-carboxylate | C22H29NO3 | 详情 | 详情 | |
| (IX) | 68383 | (3aR,4S,7aR)-4-(m-tolylethynyl)octahydro-1H-indol-4-ol hydrochloride | C17H21NO.HCl | 详情 | 详情 | |
| (X) | 16993 | methyl chlorocarbonate;Carbonochloridic acid methyl ester；[(chlorocarbonyl)oxy]methane；methyl chloroformate | 79-22-1 | C2H3ClO2 | 详情 | 详情 |
| (XI) | 10151 | Ethyleneimine; Aziridine; Azirane | 151-56-4 | C2H5N | 详情 | 详情 |
| (XII) | 26253 | 2-cyclohexen-1-one；Cyclohex-2-enone；2-cyclohexenone | 930-68-7 | C6H8O | 详情 | 详情 |
| (XIII) | 68385 | 3-(1-aziridinyl)cyclohexanone;3-(aziridin-1-yl)cyclohexanone | C8H13NO | 详情 | 详情 | |
| (XIV) | 68386 | methyl N-2-chloroethyl-N-(3-oxocyclohexyl) carbamate;methyl (2-chloroethyl)(3-oxocyclohexyl)carbamate | C10H16ClNO3 | 详情 | 详情 | |
| (XV) | 68387 | racemic methyl 4-oxooctahydroindole-1-carboxylate | C10H15NO3 | 详情 | 详情 | |
| (XVI) | 68388 | (3aR,7aR)-methyl 4-oxooctahydro-1H-indole-1-carboxylate | C10H15NO3 | 详情 | 详情 |