生物素中间体:四氢-7-乙氧羰基-3,3-五亚甲基-5-硫代-1-戊基-3H,5H-咪唑并[1,5c]噻唑的合成  

Intermediate of Biotin:Synthesis of Tetrahydro-7-ethoxycarbonyl-3.3-pentamethylene -5-thioxo-1-pentyl-3H,5H-imidazothiazole

作　　者：汪雪锋[1] 宋华付[1] 丁绍民[2] 

机构地区：[1]北京理工大学材料中心,北京100081 [2]北京春甫应用技术研究中心,北京100095

出　　处：《精细化工》2003年第1期56-57,59,共3页Fine Chemicals

摘　　要：以正庚醛为起始原料 ,α 溴化后与环己酮、氨、硫氢化钠反应合成 2 ,2 五亚甲基 5 戊基 3 噻唑啉 ,再用三氟化硼催化后 ,与异硫氰基乙酸乙酯的锂衍生物反应合成生物素中间体四氢 7 乙氧羰基 3 ,3 五亚甲基 5 硫代 1 戊基 3H ,5H 咪唑并 [1,5c]噻唑 ,收率达 17 1% ,通过Using heptaldehyde as starting material,an intermediate of biotin,tetrahydro-7-ethoxycarbonyl-3,3-pentamethylene-5-thioxo-1-pentyl-3H,5H-imidazothiazole(Ⅲ),was synthesized via three step reactions in total yield of 17.1%.Bromination of heptaldehyde gave α-bromoheptaldehyde(Ⅰ).2,2-Pentamethylene-5-pentyl-3-thiazoline(Ⅱ) was achieved by reacting Ⅰwith cyclohexanone,ammonia and sodium hydrosulfide.Ⅱ,activated by BF_3,reacted with lithium derivative of ethyl isothiocyanatoacetate to give Ⅲ.Thus the requisite biotin stereochemical skeletal structure is established.

关 键 词：生物素中间体 合成 四氢-7-乙氧羰基-3 3-五亚甲基-5-硫代-1-戊基-3H 5H-咪唑并[1 5c]噻唑 正庚醛 

分 类 号：TQ252.5[化学工程—有机化工]