[1]赵萌萌,徐崇福,宋蕴丽,等.反式-4-(N-乙酰氨基)环己醇的合成[J].常州大学学报(自然科学版),2012,(04):28-32.
　ZHAO Meng-meng,XU Chong-fu,SONG Yun-li,et al.Synthesis of Trans-4-(N-Acetylamido)Cyclohexanol[J].Journal of Changzhou University(Natural Science Edition),2012,(04):28-32.
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反式-4-(N-乙酰氨基)环己醇的合成()
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常州大学学报(自然科学版)[ISSN:2095-0411/CN:32-1822/N]

卷:
期数:
2012年04期
页码:
28-32
栏目:
出版日期:
2012-09-30

文章信息/Info

Title:
Synthesis of Trans-4-(N-Acetylamido)Cyclohexanol
作者:
赵萌萌; 徐崇福; 宋蕴丽; 富利祥; 李嘉骏
常州大学 石油化工学院,江苏 常州 213164
Author(s):
ZHAO Meng-meng; XU Chong-fu; SONG Yun-li; FU Li-xiang; LI Jia-jun
School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China
关键词:
反式-4-(N-乙酰氨基)环己醇;  催化加氢;  顺反异构;  重结晶
Keywords:
trans-4-(N-acetylamido)cyclohexanol;  catalytic hydrogenation;  cis and trans isomerism;  recrystalization
分类号:
O 624.6
文献标志码:
A
摘要:
反式-4-(N-乙酰氨基)环己醇是合成药物中间体反式-4-氨基环己醇盐酸盐的重要先行体。报道两步法合成反式-4-(N-乙酰氨基)环己醇研究结果,首先将起始原料对氨基苯酚用乙酸酐酰化,转化为对-(N-乙酰氨基)苯酚,接下来以5% Ru/C为催化剂,在有碱性助剂存在,5.0 MPa,120 ℃条件下,将其氢化为顺式和反式混合的4-(N-乙酰氨基)环己醇,转化率为100%,4-乙酰氨基环己醇的选择性达到96.9%,根据高效液相色谱法检测得知,其反式与顺式比值为78:22。最后通过重结晶分离出反式目标产物,总产率为67.0%。系统考察了多种因素对4-(N-乙酰氨基)苯酚的合成及后续催化氢化的影响。每步合成过程均由高效液相色谱监控。所有产物通过IR、1H NMR、13C NMR光谱进行了结构表征。
Abstract:
Trans-4-(N-acetylamido)cyclohexanol is an important precursor for the synthesis of pharmaceutical intermediate, hydrochloride salt of trans-4-aminocyclohexanol. Study of synthesizing trans-4-(N-acetylamido)cyclohexanol by two step processes was reported in this article. Starting material p-aminophenol was initially acetylated with acetic anhydride to yield 4-(N-acetylamido)-p-phenol, subsequenthydrogenation of this aromatic compound catalyzed by 5% Ru/C in presence of alkaline auxiliary at 5.0 MPa and 120 ℃ afforded the mixed trans-and cis-4-(N-acetylamido)cyclohexanol with 96.9% selectivity and 100% reactant conversion. The trans to cis ratio was 78 to 22 monitored by HPLC analysis. The targeted trans-isomer was isolated via recrystallization with 67.0%overall yield. Effects of myriad factors on the catalytic hydrogenation of 4-(N-acetylamido)phenol as well as acetylation of p-aminophenol wereinvestigated. Processes of each synthetic step were monitored by HPLC. The molecular structures of all the products were characterized using infrared and 1Hand 13C NMR spectroscopy respectively.

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备注/Memo

备注/Memo:
作者简介:赵萌萌(1985-),女,辽宁海城人,硕士生。
更新日期/Last Update: 2012-09-30