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【结 构 式】 
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【分子编号】39089 【品名】diethyl 3-chloropropylphosphonate 【CA登记号】 |
【 分 子 式 】C7H16ClO3P 【 分 子 量 】214.628702 【元素组成】C 39.17% H 7.51% Cl 16.52% O 22.36% P 14.43% |
合成路线1
该中间体在本合成路线中的序号：(XIII)5) The condensation of 1-chloro-3-bromopropane (XII) with dibutyl phosphonate (XIII) affords dibutyl 3-chloropropylphosphonate (XIV), which by reaction with ethyl N-benzyloxycarbamate (A) is converted into dibutyl 3-(N-benzyloxy-N-ethoxycarbonylamino)propylphosphonate (XV). Finally, this compound is hydrolyzed with HCl in acetic acid to obtain compound (I). 6) The reaction of (XII) with diethyl phosphonate (III) yields diethyl 3-chloropropylphosphonate (XVI), which by condensation with ethyl N-ethoxycarbonyl-oxycarbamate (XVII) is converted into diethyl 3-(N-ethoxycarbonyloxy-N-ethoxycarbonylamino)propylphosphonate (XVIII). Finally, this compound is hydrolyzed with HCl in acetic acid to obtain compound (I).
| 【1】 Kuroda, Y.; et al.; US 4143135 . |
| 【2】 Prous, J.R.; Castaner, J.; FR-31564. Drugs Fut 1980, 5, 5, 239. |
| 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) | 39093 | ethyl benzyloxycarbamate | C10H13NO3 | 详情 | 详情 | |
| (I) | 39088 | 3-(hydroxyamino)propylphosphonic acid | C3H10NO4P | 详情 | 详情 | |
| (III) | 12714 | diethyl phosphonate; diethyl phosphite | 762-04-9 | C4H11O3P | 详情 | 详情 |
| (XII) | 10358 | 1-Bromo-3-chloropropane | 109-70-6 | C3H6BrCl | 详情 | 详情 |
| (XIII) | 39089 | diethyl 3-chloropropylphosphonate | C7H16ClO3P | 详情 | 详情 | |
| (XIV) | 39091 | dibutyl 3-chloropropylphosphonate | C11H24ClO3P | 详情 | 详情 | |
| (XV) | 39095 | dibutyl 3-[(benzyloxy)(ethoxycarbonyl)amino]propylphosphonate | C21H36NO6P | 详情 | 详情 | |
| (XVI) | 39090 | dibutyl phosphonate | 1809-19-4 | C8H19O3P | 详情 | 详情 |
| (XVII) | 39092 | 1-[([[(ethoxycarbonyl)amino]oxy]carbonyl)oxy]ethane | C6H11NO5 | 详情 | 详情 | |
| (XVIII) | 39094 | 4-ethoxy-8-(ethoxycarbonyl)-4,10-dioxo-3,9,11-trioxa-8-aza-4lambda(5)-phosphatridecane | C13H26NO8P | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XIII)7) The condensation of dibutyl phosphonate (XIII) with N-(3-bromopropyl)-N-(p-methoxybenzyloxy)-p-toluenesulfonamide (XIX) by means of NaH in refluxing benzene gives dibutyl 3-[N-(p-methoxybenzyloxy)-N-tosylamino]propylphosphonate (XX), which is hydrolyzed with HCl in acetic acid to obtain compound (I). 8) The condensation of (XIII) with isobutyl N-(p-methoxybenzyloxy)-N-(3-bromopropyl)carbamate (XXI) with NaH in refluxing benzene affords dibutyl 3-[N-(p-methoxybenzyloxy)-N-isobutoxycarbonylamino]propylphosphonate (XXII), which is hydrolyzed with HCl in acetic acid to obtain compound (I). 9) The condensation of (XIII) with N-(3-bromopropyl)-N-benzyloxy-p-toluenesulfonamide (XXIII) with NaH in refluxing benzene gives dibutyl 3-(N-benzyloxy-N-tosylamino)propylphosphonate (XXIV), which is hydrolyzed with HCl in acetic acid to obtain compound (I).
| 【1】 Kuroda, Y.; et al.; US 4143135 . |
| 【2】 Prous, J.R.; Castaner, J.; FR-31564. Drugs Fut 1980, 5, 5, 239. |
| 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) | 39088 | 3-(hydroxyamino)propylphosphonic acid | C3H10NO4P | 详情 | 详情 | |
| (XIII) | 39089 | diethyl 3-chloropropylphosphonate | C7H16ClO3P | 详情 | 详情 | |
| (XIX) | 39096 | N-(3-bromopropyl)-N-[(4-methoxybenzyl)oxy]-4-methylbenzenesulfonamide | C18H22BrNO4S | 详情 | 详情 | |
| (XX) | 39098 | dibutyl 3-[[(4-methoxybenzyl)oxy][(4-methylphenyl)sulfonyl]amino]propylphosphonate | C26H40NO7PS | 详情 | 详情 | |
| (XXI) | 39097 | butyl 3-bromopropyl[(4-methoxybenzyl)oxy]carbamate | C16H24BrNO4 | 详情 | 详情 | |
| (XXII) | 39099 | dibutyl 3-[(butoxycarbonyl)[(4-methoxybenzyl)oxy]amino]propylphosphonate | C24H42NO7P | 详情 | 详情 | |
| (XXIII) | 39101 | N-(benzyloxy)-N-(3-bromopropyl)-4-methylbenzenesulfonamide | C17H20BrNO3S | 详情 | 详情 | |
| (XXIV) | 39100 | dibutyl 3-[(benzyloxy)[(4-methylphenyl)sulfonyl]amino]propylphosphonate | C25H38NO6PS | 详情 | 详情 |