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Drugs Today (Barc), 2008. 44(7): p. 489-501.\n[2].\nKeating, G.M., Sitafloxacin: in bacterial infections. Drugs, 2011. 71(6): p. 731-44.",[248,254],{"slug":249,"cid":250,"name":251,"nameZh":251,"cas":252,"imgSvg":253},"785893867189702700","J-1499124-0","(7S)-5-氮杂螺[2.4]...","127199-45-5","https:\u002F\u002Fapi.chemical.xiaokangmed.com\u002Fimages\u002Fchem_structures_svg\u002F135\u002F127199-45-5.svg",{"slug":255,"cid":256,"name":257,"nameZh":257,"cas":258,"imgSvg":259},"785896264955859000","J-1895627-8","8-氯-6,7-二氟-1-((...","127199-27-3","https:\u002F\u002Fapi.chemical.xiaokangmed.com\u002Fimages\u002Fchem_structures_svg\u002F473\u002F127199-27-3.svg",[],[],[],"\u003Cp>1. (1R,2S)-(-)-cis-1-叔丁氧羰基氨基-2-氟环丙烷的制备\u003Cbr \u002F>(1) N-[1-(R)-苯基乙基]-1,2-cis-2-氟代环丙烷羧酰胺｛N-[1-(R)-phenylethyl]-1,2-cis-2-Lurorcyclopanecarboxamide｝的制备\u003C\u002Fp>\u003Cp>在反应瓶中加入THF 30ml、cis-2-氟代环丙羧酸1.0g(9.62mmol)和N,N'-羰酰二咪唑1.78g(10.97mmol),将混合物于室温下搅拌反应1h.然后向该溶液中加入(R)-(+)-a-甲基苄胺1.45g(11.96mmol),再在室温下连续搅拌反应2h.减压将反应混合物溶剂蒸除.剩余物用氯仿提取,提取液用10%的柠檬酸水溶液洗涤,再用水洗涤,无水Na2SO4干燥,过滤,滤液减压蒸除溶剂,剩余物为黏性油状物,将其经硅胶(Senshu Pack SSC Silica,782-1N,Senshu Kagaku)柱[Nucleosil 50-5,20mm(内径)×250mm(长)]色谱纯化[洗脱剂:乙酸乙酯\u002FTHF(体积比9:1)],色谱过程流速为9.0ml\u002FminN-[1-(R)-苯基乙基]-1,2-cis-2-氟代环丙烷羧酰胺｛N-[1-(R)-phenylethyl]-1,2-cis-2-Lurorcyclopanecarboxamide｝的保留时间为13min,收集流出液蒸除溶剂后,余物用二异丙醚重结晶,得N-[1-(R)-苯基乙基]-1,2-cis-2-氟代环丙烷羧酰胺｛N-[1-(R)-phenylethyl]-1,2-cis-2-Lurorcyclopanecarboxamide｝精制固体.\u003C\u002Fp>\u003Cp>(2).(+)-cis-2-氟代环丙羧酸的制备\u003Cbr \u002F>在反应瓶中加入浓盐酸30ml和化合物N-[1-(R)-苯基乙基]-1,2-cis-2-氟代环丙烷羧酰胺｛N-[1-(R)-phenylethyl]-1,2-cis-2-Lurorcyclopanecarboxamide｝1.65g(7.79mmol),在搅拌下将该溶液加热至100~110ºC,在该温度下搅拌5h,冷至室温,反应混合物用NaHCO3水溶液调至pH8~9,然后用氯仿洗\u003Cbr \u002F>涤,层用浓盐酸调至pH4,用乙酸乙酯提取,取液用无水Na2SO4干燥,过滤.滤液在减压下蒸除溶剂,淡黄色油状物,无需进一步纯化,直接用于下步反应,\u003C\u002Fp>\u003Cp>(3).(1R,2S)-(-)-cis-1-叔丁氧羰基氨基-2-氟环丙烷的制备\u003C\u002Fp>\u003Cp>在反应瓶中加入叔丁醇6ml、化合物(+)-cis-2-氟代环丙羧酸265mmg(2.55mmol)、二苯基磷酰叠氮化物800mmg(2.91mmol)和三乙胺27.g(2.67mmol),搅拌加热回流,搅拌回流反应4.5h.将反应混合物减压下\u003Cbr \u002F>蒸除溶剂,剩余物用氯仿提取,提取液用10%的柠檬酸水溶液洗涤,再用2%的NaOH水溶液洗涤,最后用水洗涤,无水NaSO4干燥,过滤,滤液减压下蒸除溶剂,剩余物经硅胶柱色谱纯化[洗脱剂:氯仿],得化合物(1R,2S)-(-)-cis-1-叔丁氧羰基氨基-2-氟环丙烷.\u003C\u002Fp>\u003Cp>2. (S)-(-)-7-叔丁氧羰基氨基-5-氮杂螺[2,4]庚烷的制备\u003Cbr \u002F>(1) 5-[1-(1R)-苯基乙基]-4,7-二氧代-5-氮杂螺{2,4]庚烷的制备\u003Cbr \u002F>在反应瓶中加入乙酰乙酸乙酯10.4g(79.91mmol)、1,2-二溴乙烷15g(79.85mmol)、碳酸钾23g(166.66mmol)和DMF150ml,在室温下将该混合物搅拌反应2天.过滤除去不溶物#滤液在减压下蒸除溶剂至干,剩余物加水适量,用氯仿提取,氯仿提取液用无水NaSO4干燥,过滤,滤液减压蒸除溶剂,剩余物为淡黄色油状物,进行减压蒸馏,收集70~71ºC\u002F267~339.9Pa,馏分,该馏分化合物为1-乙酰基-1-\u002F环丙羧酸乙酯,bp70~71ºC\u002F2~3mmHg(267~339.9Pa).\u003C\u002Fp>\u003Cp>\u003Csup>1\u003C\u002Fsup>H-NMR(CDCl3)δ：1.30(3H,t,J＝7Hz,1.48(4H,s),2.49(3H,s),4.24(2H,q,J＝7Hz)\u003C\u002Fp>\u003Cp>在反应瓶中加入乙醇200ml、上述制备的1-乙酰基-1-环丙羧酸乙酯35.7g(0.23mol),在室温下搅拌\u003Cbr \u002F>滴加溴素40g(0.25mol),滴毕,继续在室温搅拌反应2h.减压下蒸除过量的溴和溶剂,剩余物则为粗制1-溴乙酰基-1-环丙羧酸乙酯,不经进一步纯化,加入乙醇200ml溶解,搅拌下往该溶液中同时滴加(R)-(+)-1-苯基乙胺33g(0.27mol)和三乙胺27g(0.27mol),在1h内同时滴完,滴加过程中用冰浴冷却.滴加毕,将反应液温升至室温,于室温下连续搅拌反应2天.过滤除去不溶物,滤液在减压下除去乙醇,剩余物用乙酸乙酯300ml溶解,溶液用1mol\u002FL盐酸洗涤,用饱和NaHCO3水溶液洗涤,最后用饱和食盐水洗涤,有机层用无水NaSO4干燥,过滤,滤液减压蒸除溶剂,剩余物经硅胶(200g硅胶)柱色谱纯化,用0~2%乙醇氯仿溶液洗脱,经后处理\u003Cbr \u002F>得化合物5-[1-(1R)-苯基乙基]-4,7-二氧代-5-氮杂螺{2,4]庚烷,该产物为无色结晶.\u003C\u002Fp>\u003Cp>\u003Csup>1\u003C\u002Fsup>H-NMR(CDCl3)δ:1.62(3H,d,J=7.2Hz),3.50(1H,d,J=18Hz),3.90(1H,d,J=18Hz),5.82(1H,q,J=7.2Hz),7.36(5H,s)\u003C\u002Fp>\u003Cp>(2) 5-[(1R)-苯基乙基]-7-肟基-4-氧代-5-氮杂螺[2,4]庚烷的制备\u003Cbr \u002F>在反应瓶中加入化合物5-[1-(1R)-苯基乙基]-4,7-二氧代-5-氮杂螺{2,4]庚烷3.35g(14.63mmol)、盐酸羟胺1.6g(23.02mmol)、三乙胺23.g(22.77mmol)和乙醇80ml,于室温下搅拌反应2h.将反应混合物于减压下蒸除溶剂.剩余物加氯仿溶解,用10%柠檬酸水溶液洗涤,再用饱和氯化钠水溶液洗涤,有机层用无水Na2SO4干燥,过滤#滤液减压下蒸除溶剂,得无色晶体5-[(1R)-苯基乙基]-7-肟基-4-氧代-5-氮杂螺[2,4]庚烷3.5g,收率98%.\u003C\u002Fp>\u003Cp>\u003Csup>1\u003C\u002Fsup>H-NMR(CDCl3)δ:1.20~1.40(2H,m),1.53(3H,d,J=7.2Hz和2H,m),3.80(1H,d,J=18Hz),4.16(1H,d,J=18Hz),5.63(3H,d,J=7.2Hz)7.32(5H,s).\u003C\u002Fp>\u003Cp>(3) 7-氨基-4-氧代-5-[(1R)-苯乙基]-5-氮杂螺[2,4]庚烷的制备\u003Cbr \u002F>在氢化反应瓶中加入甲醇150ml、化合物5-[(1R)-苯基乙基]-7-肟基-4-氧代-5-氮杂螺[2,4]庚烷3.5g(14.34mmol)和7.5ml雷内镍催化剂,于室温下常压通氢气(通氢前预先用N2置换瓶中空气)搅拌反应12h.过滤掉催化剂#滤液在减压下蒸除溶剂,剩余物经硅胶(100g硅胶装柱)柱色谱纯化[洗脱剂:5%甲醇\u002F氯仿混合溶剂],先流出的洗脱组分为7-氨基-4-氧代-5-[(1R)-苯乙基]-5-氮杂螺[2,4]庚烷得7-氨基-4-氧代-5-[(1R)-苯乙基]-5-氮杂螺[2,4]庚烷1.0g,后流出的洗脱组分为其异构物,得量为0.8g.两者都是无色油状物.7-氨基-4-氧代-5-[(1R)-苯乙基]-5-氮杂螺[2,4]庚烷的波谱数据如下.\u003C\u002Fp>\u003Cp>\u003Csup>1\u003C\u002Fsup>H-NMR(CDCl3)δ:0.8~1.40(4H,m),1.52(3H,d,J=7Hz),2.87(1H,dd,J=10Hz和3Hz),3.30~3.90(2H,m),4.27(2H,br,s),5.42(1H,q,J=7Hz),7.29(5H,s).\u003C\u002Fp>\u003Cp>(4) 7-氨基-5-[(1R)-苯乙基]-5-氮杂螺[2,4]庚烷的制备\u003Cbr \u002F>在反应瓶中(经充分干燥}加入无水THF50ml,化合物7-氨基-4-氧代-5-[(1R)-苯乙基]-5-氮杂螺[2,4]庚烷1.0g(4.35mmol)和氢化锂铝(LiAlH4)500mg(13.16mmol),将混合物搅拌回流反应17h.冷却后#按顺序向反应混合物中加入水0.5ml、15%NaOH水溶液0.5ml和水1.5ml,于室温下搅拌30min.过滤除去不溶物,不溶物滤渣用适量THF洗涤,抽干.合并滤液和洗液,用无NaSO4干燥,过滤,滤液减压下蒸除溶剂,剩余淡黄色油状物7-氨基-5-[(1R)-苯乙基]-5-氮杂螺[2,4]庚烷940mgmg.\u003C\u002Fp>\u003Cp>\u003Csup>1\u003C\u002Fsup>H-NMR(CDCl3)δ:0.20~0.80(4H,m),1.35(3H,d,J=6.6Hz),0.60~2.0(2H,br,m),2.20~3.10(4H,m),3.27(1H,q,J=6.6Hz),3.50~3.90(1H,m),7.28(5H,br,s).\u003C\u002Fp>\u003Cp>(5) 7-(叔丁氧羰基氨基)-5-[(1R)-苯乙基]-5-氮杂螺[2,4]庚烷的制备\u003Cbr \u002F>在干燥反应瓶中加入无水THF20ml、化合物7-氨基-5-[(1R)-苯乙基]-5-氮杂螺[2,4]庚烷764mg(3.57mmol)和2-(叔丁氧羰基氧亚氨基)-2-苯基乙腈(Boc-ON)1.3g(5.28mmol),将该混合物于室温下搅拌反应4h.向反应混合物中加入乙酸乙酯适量,搅拌,然后用1mol\u002FLNaOH水溶液洗涤混合物两次,水洗一次,着用10%的柠檬酸水溶液提取,提取液用乙酸乙酯洗涤一次.向水层加入15%NaOH水溶液(在冷却下加,使成碱),然后将其混合物用氯仿提取3次,有机层用饱和氯化钠水溶液洗涤,后用无水NaSO4干燥,过滤,滤液减压下蒸除溶剂,剩余物经硅胶柱色谱纯化[硅胶20g,洗脱剂:氯仿\u002F甲醇(20:1,10:1)],得7-(叔丁氧羰基氨基)-5-[(1R)-苯乙基]-5-氮杂螺[2,4]庚烷690mg.将其用正己烷洗涤,得到的晶体为无色,收率61.2%.\u003C\u002Fp>\u003Cp>\u003Csup>1\u003C\u002Fsup>H-NMR(CDCl3)δ:0.40~0.90(4H,m),1.36(3H,d,J=7.2Hz),1.44(9H,s),2.42(2H,ABq,J=10Hz),2.79(2H,d,J=5.6Hz),3.24(1H,q,J=7.2Hz),3.6~4.0(1H,m),4.60~5.10(1H,br,d),7.28(5H,s).\u003C\u002Fp>","2026-08-21T07:51:12.859463Z",false,[267,273,279,284,290,296],{"slug":268,"cid":269,"name":270,"nameZh":271,"cas":272},"785895040399446016","J-1110640-3","Solvent Red 27","溶剂红27","1320-06-5",{"slug":274,"cid":275,"name":276,"nameZh":277,"cas":278},"785871874079854592","J-1110697-5","Crystal Violet","结晶紫","548-62-9",{"slug":280,"cid":281,"name":282,"nameZh":282,"cas":283},"785914490636996608","J-1241469-7","2-Chloro-4-(1-dibenzofuranyl)-6-(1-naphthalenyl)-1,3,5-triazine","2417986-80-0",{"slug":285,"cid":286,"name":287,"nameZh":288,"cas":289},"785897866148188160","J-1065587-2","Noscapine","那可丁","128-62-1",{"slug":291,"cid":292,"name":293,"nameZh":294,"cas":295},"785881331014832128","J-18850-2","Diosgenin","薯蓣皂苷元","512-04-9",{"slug":297,"cid":298,"name":299,"nameZh":300,"cas":301},"785872510607429632","J-1334045-0","calcium saccharin","糖精钙","6485-34-3",1792658255966,"zh-CN",[]]