使用(S)-2-甲氧基-2-(1-萘基)丙酸制备半翅目象甲的信息素单一对映体2-甲基-4-庚醇。
Preparation of single-enantiomer 2-methyl-4-heptanol, a pheromone of Metamasius hemipterus, using (S)-2-methoxy-2-(1-naphthyl)propionic acid.
作者信息
Ichikawa Akio, Ono Hiroshi
机构信息
National Institute of Agrobiological Sciences, 1-2 Owashi, Tsukuba, Ibaraki 305-8634, Japan.
出版信息
J Chromatogr A. 2006 Jun 2;1117(1):38-46. doi: 10.1016/j.chroma.2006.03.100. Epub 2006 Apr 24.
To investigate the resolution of secondary alcohols using 2-methoxy-2-(1-naphthyl)propionic acid (MalphaNP acid), 2-methyl-4-heptanol, one of the aggregation pheromones of Metamasius hemipterus, was resolved using (S)-MalphaNP acid. As a chiral-resolving agent, MalphaNP acid is superior to 3,3,3-trifluoro-2-methoxy-2-phenylpropionic acid (MTPA) in terms of HPLC separation and NMR shielding. A better separation of diastereomeric MalphaNP esters was observed when n-hexane-THF was used as the eluent for silica gel HPLC. The solvolysis of the diastereomeric MalphaNP esters gave (R)-2-methyl-4-heptanol and its enantiomer; enantiopure (S)-MalphaNP acid was also recovered. In addition, the preferred conformation of the MalphaNP ester was confirmed using methyl (R)-3-hydroxyvalerate as an authentic compound.
为了研究使用2-甲氧基-2-(1-萘基)丙酸（MalphaNP酸）拆分仲醇，使用(S)-MalphaNP酸拆分了半翅目变色树蜥聚集信息素之一的2-甲基-4-庚醇。作为一种手性拆分剂，MalphaNP酸在高效液相色谱（HPLC）分离和核磁共振（NMR）屏蔽方面优于3,3,3-三氟-2-甲氧基-2-苯基丙酸（MTPA）。当正己烷-四氢呋喃用作硅胶HPLC的洗脱剂时，观察到非对映体MalphaNP酯的分离效果更好。非对映体MalphaNP酯的溶剂解得到(R)-2-甲基-4-庚醇及其对映体；还回收了对映体纯的(S)-MalphaNP酸。此外，使用(R)-3-羟基戊酸甲酯作为标准化合物确定了MalphaNP酯的优势构象。
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