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【结 构 式】 
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【分子编号】12127 【品名】3-Chloro-2-methyl-1-propene; Isobutenyl chloride 【CA登记号】563-47-3 |
【 分 子 式 】C4H7Cl 【 分 子 量 】90.55228 【元素组成】C 53.06% H 7.79% Cl 39.15% |
合成路线1
该中间体在本合成路线中的序号：(VI)The malonic synthesis of 4-nitrochlorobenzene (VIII) with sodium diethyl methylmalonate (IX) (prepared with the corresponding malonic ester and NaH) in hot DMF gives diethyl (4-nitrophenyl)methylmalonate (X), which is reduced with H2 over Pd/C as before yielding diethyl (4-aminophenyl)methylmalonate (XI). The alkylation of (XI) with (VI) by means of NaHCO3 in refluxing ethanol affords diethyl [4-(2-methylallyl)aminophenyl]methylmalonate (XII), which is treated with sodium ethoxide in refluxing ethanol to yield ethyl 2-(4-[2-methylallylamino)phenyl]propionate (XIV). Finally, this compound is hydrolyzed with NaOH in refluxing ethanol. Partial hydrolysis of (XII) with NaOH in refluxing ethanol gives 2-[4-(2-methylallylamino)phenyl]methylmalonic acid (XIII), which is finally decarboxylated by treatment with refluxing aqueous HCl. The simultaneous hydrolysis and decarboxylation of (XII) with NaOH in refluxing ethanol also gives the title product.
| 【1】 Dumaitre, B.; et al.; Synthesis of some analgesic and antiinflammatory 4-aminophenylacetic and 4-aminophenylacetic and 2-(4-aminophenyl)propionic acid derivatives. Eur J Med Chem - Chim Ther 1979, 14, 3, 207-214. |
| 【2】 Serradell, M.N.; Castaner, J.; Alminoprofen. Drugs Fut 1984, 9, 3, 165. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VI) | 12127 | 3-Chloro-2-methyl-1-propene; Isobutenyl chloride | 563-47-3 | C4H7Cl | 详情 | 详情 |
| (VIII) | 13909 | 1-Chloro-4-nitrobenzene; p-Nitrochlorobenzene | 100-00-5 | C6H4ClNO2 | 详情 | 详情 |
| (IX) | 30310 | diethyl 2-methylmalonate | 609-08-5 | C8H14O4 | 详情 | 详情 |
| (X) | 13910 | diethyl 2-methyl-2-(4-nitrophenyl)malonate | C14H17NO6 | 详情 | 详情 | |
| (XI) | 30311 | diethyl 2-(4-aminophenyl)-2-methylmalonate | C14H19NO4 | 详情 | 详情 | |
| (XII) | 30312 | diethyl 2-methyl-2-[4-[(2-methyl-2-propenyl)amino]phenyl]malonate | C18H25NO4 | 详情 | 详情 | |
| (XIII) | 30313 | 2-methyl-2-[4-[(2-methyl-2-propenyl)amino]phenyl]malonic acid | C14H17NO4 | 详情 | 详情 | |
| (XIV) | 30314 | ethyl 2-[4-[(2-methyl-2-propenyl)amino]phenyl]propanoate | C15H21NO2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VI)The reaction of 4-nitrophenylacetic acid (I) with formaldehyde and dimethylamine in water gives 2-(4-nitrophenyl)-3-(dimethylamino)propionic acid (II), which by treatment with refluxing concentrated HCl is converted into 2-(4-nitrophenyl)acrylic acid (III). The esterification of (III) with methanol and p-toluenesulfonic acid yields the corresponding methyl ester (IV), which is reduced with H2 over Pd/C in ethanol to afford methyl 2-(4-aminophenyl)propionate (V). The alkylation of (V) with 2-methylallyl chloride (VI) by means of pyridine in refluxing ethanol gives methyl 2-[4-(2-methylallylamino)phenyl]propionate (VII), which is finally hydrolyzed with NaOH in refluxing methanol.
| 【1】 Dumaitre, B.; et al.; Synthesis of some analgesic and antiinflammatory 4-aminophenylacetic and 4-aminophenylacetic and 2-(4-aminophenyl)propionic acid derivatives. Eur J Med Chem - Chim Ther 1979, 14, 3, 207-214. |
| 【2】 Bouchara, E. (Laboratoires du Dr. E. Bouchara); Nouveau procede de preparation de derives de l'acide phenylacetique. FR 2289180 . |
| 【3】 Serradell, M.N.; Castaner, J.; Alminoprofen. Drugs Fut 1984, 9, 3, 165. |
| 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) | 30305 | 2-(4-nitrophenyl)acetic acid | 104-03-0 | C8H7NO4 | 详情 | 详情 |
| (II) | 30306 | N,N-dimethyl-2-(4-nitrophenyl)-beta-alanine | C11H14N2O4 | 详情 | 详情 | |
| (III) | 30307 | 2-(4-nitrophenyl)acrylic acid | C9H7NO4 | 详情 | 详情 | |
| (IV) | 30308 | methyl 2-(4-nitrophenyl)acrylate | C10H9NO4 | 详情 | 详情 | |
| (V) | 13912 | methyl 2-(4-aminophenyl)propanoate | 39718-97-3 | C10H13NO2 | 详情 | 详情 |
| (VI) | 12127 | 3-Chloro-2-methyl-1-propene; Isobutenyl chloride | 563-47-3 | C4H7Cl | 详情 | 详情 |
| (VII) | 30309 | methyl 2-[4-[(2-methyl-2-propenyl)amino]phenyl]propanoate | C14H19NO2 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(XV)Three related new synthetic routes for E-1020 have been reported: 1) The cyclization of 2-bromoacetaldehyde diethylacetal (I) with 2-aminopyridine-5-carboxylic acid methyl ester (II) by means of HCl in hot water gives imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester (III), which is reduced with dibutylaluminum hydride in dichloromethane to the corresponding aldehyde (IV). The condensation of (IV) with nitroethane (V) by means of butylamine in refluxing ethanol affords 6-(2-nitro-1-propenyl)imidazo[1,2-a]pyridine (VI), which is treated with Fe-FeCl2-HCl in hot ethanol-water to give 1-(imidazo[1,2-a]pyridyl-6-yl)-2-propanone (VII). The condensation of (VII) with dimethylformamide dimethylacetal (VIII) in hot DMF yields 4-(dimethylamino)-3-(imidazo[1,2-a]pyridin-6-yl)-3-buten-2-one (IX), which is finally cyclized with cyanacetamide (X) by means of sodium methoxide in hot DMF. 2) The cyclization of acetal (I) with 2-amino-5-bromopyridine (XI) as before gives 6-bromoimidazo[1,2-a]pyridine (XII), which is condensed with potassium acetylacetonate (XIII) by means of KI and Cu2I2 in hot DMF yielding the adduct (XIV). The cleavage of (XIV) with NaOH and then with HCl gives the propanone (VII), already obtained. 3) The condensation of the bromo derivative (XII) with 3-chloro-2-methylpropene (XV) by means of ethylmagnesium bromide in hot THF gives 6-isobutenylimidazo[1,2-a]pyridine (XVI), which is ozonolyzed with O3 in methanol-water-HCl to yield the propanone (VII), already obtained.
| 【1】 Yamanaka, M.; Miyake, K.; Suda, S.; Ohhara, H.; Ogawa, T.; Imidazo[1,2-a]pyridines. I. Synthesis and inotropic activity of new 5-imidazo[1,2-a]pyridinyl-2(1H)-pyridinone derivatives. Chem Pharm Bull 1991, 39, 6, 1556-67. |
| 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) | 12113 | 2-Bromo-1-ethoxyethyl ethyl ether; 2-Bromo-1,1-diethoxyethane; Bromoacetaldehyde diethylacetal | 2032-35-1 | C6H13BrO2 | 详情 | 详情 |
| (II) | 12114 | methyl 6-aminonicotinate | C7H8N2O2 | 详情 | 详情 | |
| (III) | 12115 | methyl imidazo[1,2-a]pyridine-6-carboxylate | C9H8N2O2 | 详情 | 详情 | |
| (IV) | 12116 | Imidazo[1,2-a]pyridine-6-carbaldehyde | C8H6N2O | 详情 | 详情 | |
| (V) | 12117 | Nitroethane; 1-Nitroethane | 79-24-3 | C2H5NO2 | 详情 | 详情 |
| (VI) | 12118 | 6-[(E)-2-Nitro-1-propenyl]imidazo[1,2-a]pyridine | C10H9N3O2 | 详情 | 详情 | |
| (VII) | 12119 | 1-Imidazo[1,2-a]pyridin-6-ylacetone | C10H10N2O | 详情 | 详情 | |
| (VIII) | 11984 | N-(Dimethoxymethyl)-N,N-dimethylamine;dimethylformamide dimethylacetal;1,1-dimethoxy-N,N-dimethylmethanamine； Dimethoxy-N,N-dimethylmethanamine; N,N-Dimethylformamide dimethyl acetal | 4637-24-5 | C5H13NO2 | 详情 | 详情 |
| (IX) | 12121 | (Z)-4-(Dimethylamino)-3-imidazo[1,2-a]pyridin-6-yl-3-buten-2-one | C13H15N3O | 详情 | 详情 | |
| (X) | 12122 | Cyanoacetamide; 2-Cyanoacetamide | 107-91-5 | C3H4N2O | 详情 | 详情 |
| (XI) | 12123 | 5-Bromo-2-pyridinylamine; 5-Bromo-2-pyridinamine; 2-Amino-5-bromopyridine | 1072-97-5 | C5H5BrN2 | 详情 | 详情 |
| (XII) | 12124 | 6-Bromoimidazo[1,2-a]pyridine | 6188-23-4 | C7H5BrN2 | 详情 | 详情 |
| (XIII) | 12125 | [2-Methoxy-1-(methoxycarbonyl)-2-oxoethyl]potassium | C5H7KO4 | 详情 | 详情 | |
| (XIV) | 12126 | 3-Imidazo[1,2-a]pyridin-6-yl-2,4-pentanedione | C12H12N2O2 | 详情 | 详情 | |
| (XV) | 12127 | 3-Chloro-2-methyl-1-propene; Isobutenyl chloride | 563-47-3 | C4H7Cl | 详情 | 详情 |
| (XVI) | 12128 | 6-(2-Methyl-2-propenyl)imidazo[1,2-a]pyridine | C11H12N2 | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(II)1) The condensation of 6-bromoimidazo[1,2-a]-pyridine (I) with 2-(chloromethyl)propene (II) by means of Mg and ethyl bromide in THF gives 6-(2-methyl-2-propenyl)imidazo[1,2-a]pyridine (III), which is ozonolyzed with O3 yielding 1-(imidazo[1,2-a]-pyridin-6-yl)-2-propanone (IV). The condensation of (IV) with dimethylformamide dimethylketal (V) in hot DMF affords 4-(dimethylamino)-3-(imidazo[1,2-a]-pyridin-6-yl)-3-buten-2-one (IV), which is finally cyclized with 2-cyanoacetamide (VII) by means of sodium methoxide in hot DMF.
| 【1】 Miyake, K.; Ohhara, H.; Suda, S.; Toshiaki, O.; Yamanaka, M. (Eisai Co., Ltd.); 5-(6-Imidazo[1,2-a]pyridyl)pyridine derivs.. EP 0199127; ES 8706146; ES 8708230; ES 8708231; ES 8801654; ES 8801655; JP 1986218589; US 4751227 . |
| 【2】 Prous, J.; Castaner, J.; E-1020. Drugs Fut 1988, 13, 6, 514. |
| 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) | 12124 | 6-Bromoimidazo[1,2-a]pyridine | 6188-23-4 | C7H5BrN2 | 详情 | 详情 |
| (II) | 12127 | 3-Chloro-2-methyl-1-propene; Isobutenyl chloride | 563-47-3 | C4H7Cl | 详情 | 详情 |
| (III) | 12128 | 6-(2-Methyl-2-propenyl)imidazo[1,2-a]pyridine | C11H12N2 | 详情 | 详情 | |
| (IV) | 12119 | 1-Imidazo[1,2-a]pyridin-6-ylacetone | C10H10N2O | 详情 | 详情 | |
| (V) | 11984 | N-(Dimethoxymethyl)-N,N-dimethylamine;dimethylformamide dimethylacetal;1,1-dimethoxy-N,N-dimethylmethanamine； Dimethoxy-N,N-dimethylmethanamine; N,N-Dimethylformamide dimethyl acetal | 4637-24-5 | C5H13NO2 | 详情 | 详情 |
| (VI) | 12121 | (Z)-4-(Dimethylamino)-3-imidazo[1,2-a]pyridin-6-yl-3-buten-2-one | C13H15N3O | 详情 | 详情 | |
| (VII) | 12122 | Cyanoacetamide; 2-Cyanoacetamide | 107-91-5 | C3H4N2O | 详情 | 详情 |
合成路线5
该中间体在本合成路线中的序号：(III)1) The esterification of 5-chloro-2-hydroxybenzoic acid (I) with methanol - HCl gives the corresponding methyl ester (II), which is alkylated with 3-chloro-2-methylpropene (III) to afford methyl 5-chloro-2-(2-methyl-2-propenyloxy)benzoate (IV). The rearrangement of (IV) by heating with N-methylpyrrolidine yields methyl 5-chloro-2-hydroxy-3-(2-methyl-2-propenyl)benzoate (V). The cyclization of (V) in formic acid followed by hydrolysis with NaOH gives 5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylic acid (VI), which is finally treated with SOCl2, condensed with 3alpha-aminotropane (VII) and treated with maleic acid.
| 【1】 Cohen, M.L.; Lacefield, W.B. (Eli Lilly and Company); Improvements in or relating to specific 5-HT3 antagonists. AU 8821916; EP 0307172; JP 1989110684 . |
| 【2】 Robertson, D.W.; Bloomquist, W.; Pfiefer, W.; Cohen, M.L.; Simon, R.L.; Lacefield, W.B.; Zatosetron, a potent, selective, and long-acting 5-HT3 receptor antagonist: Synthesis and structure-activity relationships. J Med Chem 1992, 35, 2, 310-9. |
| 【3】 Graul, A.; Castaner, J.; Prous, J.; Zatosetron Maleate. Drugs Fut 1994, 19, 9, 850. |
| 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) | 13895 | 5-Chloro-2-hydroxybenzoic acid; 5-Chlorosalicylic acid | 321-14-2 | C7H5ClO3 | 详情 | 详情 |
| (II) | 13714 | Methyl 5-chloro-2-hydroxybenzoate; Methyl 5-chlorosalicylate | 4068-78-4 | C8H7ClO3 | 详情 | 详情 |
| (III) | 12127 | 3-Chloro-2-methyl-1-propene; Isobutenyl chloride | 563-47-3 | C4H7Cl | 详情 | 详情 |
| (IV) | 13898 | methyl 5-chloro-2-[(2-methyl-2-propenyl)oxy]benzoate | C12H13ClO3 | 详情 | 详情 | |
| (V) | 13899 | methyl 5-chloro-2-hydroxy-3-(2-methyl-2-propenyl)benzoate | C12H13ClO3 | 详情 | 详情 | |
| (VI) | 13900 | 5-Chloro-2,2-dimethyl-2,3-dihydro-1-benzofuran-7-carboxylic acid | C11H11ClO3 | 详情 | 详情 | |
| (VII) | 12412 | (1R,5S)-8-Methyl-8-azabicyclo[3.2.1]octan-3-amine; (1R,5S)-8-Methyl-8-azabicyclo[3.2.1]oct-3-ylamine | C8H16N2 | 详情 | 详情 |
合成路线6
该中间体在本合成路线中的序号：(III)2) The title compound, with or without [14C]-radiolabeling at the carboxamide group, is synthesized as follows: The alkylation of 2-bromo-4-chlorophenol (VIII) with 2-methylallyl chloride (III) by means of cesium carbonate in acetone gives the corresponding allyl ether (IX), which is submitted to an allylic transposition to the ortho allyl phenol (X); the latter, without isolation, is thermically cyclized to 7-bromo-5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran (XI). The reaction of (XI) with KCN (with or without [14C]-radiolabel) by means of CuCN yields 5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-carbonitrile (XII), which is hydrolyzed with methanolic KOH to the corresponding acid (XIII). The reaction of (XIII) with oxalyl chloride in toluene affords the corresponding acyl chloride (XIV), which is finally condensed with endo-3-amino-8-methyl-8-azabicyclo[3.2.1]octane (3alpha-aminotropane) (VII) in toluene as solvent.
| 【1】 O'Bannon, D.D.; Wheeler, W.J.; The synthesis of the carbonyl-14C analog of zatosetron maleate, a potent, long-acting, orally effective 5-HT3 receptor antagonist. J Label Compd Radiopharm 1991, 29, 6, 625-32. |
| 【2】 Graul, A.; Castaner, J.; Prous, J.; Zatosetron Maleate. Drugs Fut 1994, 19, 9, 850. |
| 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) | 12127 | 3-Chloro-2-methyl-1-propene; Isobutenyl chloride | 563-47-3 | C4H7Cl | 详情 | 详情 |
| (VII) | 12412 | (1R,5S)-8-Methyl-8-azabicyclo[3.2.1]octan-3-amine; (1R,5S)-8-Methyl-8-azabicyclo[3.2.1]oct-3-ylamine | C8H16N2 | 详情 | 详情 | |
| (VIII) | 13902 | 2-Bromo-4-chlorophenol | 695-96-5 | C6H4BrClO | 详情 | 详情 |
| (IX) | 13903 | 2-Bromo-4-chlorophenyl 2-methyl-2-propenyl ether; 2-Bromo-4-chloro-1-[(2-methyl-2-propenyl)oxy]benzene | C10H10BrClO | 详情 | 详情 | |
| (X) | 13904 | 2-Bromo-4-chloro-6-(2-methyl-2-propenyl)phenol | C10H10BrClO | 详情 | 详情 | |
| (XI) | 13905 | 7-Bromo-5-chloro-2,2-dimethyl-2,3-dihydro-1-benzofuran | C10H10BrClO | 详情 | 详情 | |
| (XII) | 13906 | 5-Chloro-2,2-dimethyl-2,3-dihydro-1-benzofuran-7-carbonitrile | C11H10ClNO | 详情 | 详情 | |
| (XII) | 45187 | 5-chloro-2,2-dimethyl-2,3-dihydro-1-benzofuran-7-carboxylic acid | C11H11ClO3 | 详情 | 详情 | |
| (XIII) | 13900 | 5-Chloro-2,2-dimethyl-2,3-dihydro-1-benzofuran-7-carboxylic acid | C11H11ClO3 | 详情 | 详情 | |
| (XIII) | 45188 | 5-chloro-2,2-dimethyl-2,3-dihydro-1-benzofuran-7-carbonitrile | C11H10ClNO | 详情 | 详情 | |
| (XIV) | 13908 | 5-Chloro-2,2-dimethyl-2,3-dihydro-1-benzofuran-7-carbonyl chloride | C11H10Cl2O2 | 详情 | 详情 | |
| (XIV) | 45189 | 5-chloro-2,2-dimethyl-2,3-dihydro-1-benzofuran-7-carbonyl chloride | C11H10Cl2O2 | 详情 | 详情 |
合成路线7
该中间体在本合成路线中的序号：(II)The reaction of 5-chloro-2-hydroxybenzoic acid (I) with 2-methyl-2-propenyl chloride (II) by means of K2CO3 and KI in hot DMF gives 5-chloro-2-(2-methyl-2-propenyloxy)benzoic acid 2-methyl-2-propenyl ester (III), which is rearranged by heating at 190 C yielding 5-chloro-2-hydroxy-3-(2-methyl-2-propenyl)benzoic acid 2-methyl-2-propenyl ester (IV). The cyclization of (IV) with refluxing 90% formic acid affords 5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylic acid (V), which is treated with SOCl2 in DMF and condensed with endo-8-methyl-8-azabicyclo[3.2.1]octan-3-amine (VI). The acid intermediate (V) can also be obtained by hydrolysis of the ester (III) with NaOH and tetrabutylammonium bisulfate in refluxing water to give 5-chloro-2-(2-methyl-2-propenyloxy)benzoic acid (VII), which is rearranged by heating at 170 C yielding 5-chloro-2-hydroxy-3-(2-methyl-2-propenyl)benzoic acid (VIII). Finally, (VIII) is cyclized to acid intermediate (V) by a treatment with aqueous refluxing 2.7N HCl. The intermediate endo-8-methyl-8-azabicyclo[3.2.1]octan-3-amine (VI) has been obtained as follows: 2,5-dihydroxytetrahydrofuran (IX) or 2,5-dimethoxytetra-hydrofuran (X) with HCl give butanedialdehyde (XI), which, without isolation, is cyclized with 3-oxoglutaric acid (XII) and methylamine by means of NaOAc and HCl in hot water yielding 8-methyl-8-azabicyclo[3.2.1]octan-3-one (XIII). The reductocondensation of (XIII) with benzylamine by means of NaBH(OAc)3, followed by hydrogenolysis with H2 over Pd/C in basic water gives directly the amine (VI). The intermediate amine (VI) can also be obtained by condensation of bicyclooctanone (XIII) with benzylamine(A) to give the imine (XIV), which is reduced to the benzylamine (XV) with H2 over PtO2 in ethanol. Finally, this compound is debenzylated by hydrogenation over Pd/C in the same solvent yielding amine (VI).
| 【1】 Burks, J.E.; et al.; Development of a manufacturing process for zatosetron maleate. Org Process Res Dev 1997, 1, 3, 198. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 15147 | Benzylamine; Phenylmethanamine | 100-46-9 | C7H9N | 详情 | 详情 |
| (I) | 13895 | 5-Chloro-2-hydroxybenzoic acid; 5-Chlorosalicylic acid | 321-14-2 | C7H5ClO3 | 详情 | 详情 |
| (II) | 12127 | 3-Chloro-2-methyl-1-propene; Isobutenyl chloride | 563-47-3 | C4H7Cl | 详情 | 详情 |
| (III) | 36355 | 2-methyl-2-propenyl 5-chloro-2-[(2-methyl-2-propenyl)oxy]benzoate | C15H17ClO3 | 详情 | 详情 | |
| (IV) | 36356 | 2-methyl-2-propenyl 5-chloro-2-hydroxy-3-(2-methyl-2-propenyl)benzoate | C15H17ClO3 | 详情 | 详情 | |
| (V) | 13900 | 5-Chloro-2,2-dimethyl-2,3-dihydro-1-benzofuran-7-carboxylic acid | C11H11ClO3 | 详情 | 详情 | |
| (VI) | 12412 | (1R,5S)-8-Methyl-8-azabicyclo[3.2.1]octan-3-amine; (1R,5S)-8-Methyl-8-azabicyclo[3.2.1]oct-3-ylamine | C8H16N2 | 详情 | 详情 | |
| (VII) | 36357 | 5-chloro-2-[(2-methyl-2-propenyl)oxy]benzoic acid | C11H11ClO3 | 详情 | 详情 | |
| (VIII) | 36358 | 5-chloro-2-hydroxy-3-(2-methyl-2-propenyl)benzoic acid | C11H11ClO3 | 详情 | 详情 | |
| (IX) | 36359 | tetrahydro-2,5-furandiol | C4H8O3 | 详情 | 详情 | |
| (X) | 12132 | 2,5-Dimethoxytetrahydrofuran; 5-Methoxytetrahydro-2-furanyl methyl ether | 696-59-3 | C6H12O3 | 详情 | 详情 |
| (XI) | 36360 | succinaldehyde | C4H6O2 | 详情 | 详情 | |
| (XII) | 15530 | 1,3-Acetonedicarboxylic Acid; 3-Oxopentanedioic acid；3-oxoglutaric acid | 542-05-2 | C5H6O5 | 详情 | 详情 |
| (XIII) | 16443 | (1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-one | C8H13NO | 详情 | 详情 | |
| (XIV) | 36361 | N-benzyl-N-[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-ylidene]amine; N-[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-ylidene](phenyl)methanamine | C15H20N2 | 详情 | 详情 | |
| (XV) | 12413 | N-Benzyl-N-[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]amine; (1R,5S)-N-Benzyl-8-methyl-8-azabicyclo[3.2.1]octan-3-amine | C15H22N2 | 详情 | 详情 |