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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (08): 989-993. 上一篇    下一篇

研究论文

手性3,5-二甲基-2-芳基-2-吗啉醇盐酸盐的合成及其晶体结构

肖新荣*，袁亚莉，祝良勇，陈孟辉   

  1. (南华大学化学化工学院 衡阳 421001)
  • 收稿日期:2006-10-23 修回日期:1900-01-01 发布日期:2007-07-30
  • 通讯作者: 肖新荣*

Synthesis and Crystal Structure of Chiral 2-Aryl-3,5-dimethyl-2- morpholinol Hydrochloride

XIAO Xin-Rong*, YUAN Ya-Li, ZHU Niang-Yong, CHEN Meng-Hui   

  1. (College of Chemistry and Chemical Engineering, Nanhua University, Hengyang 421001)
  • Received:2006-10-23 Revised:1900-01-01 Published:2007-07-30
  • Contact: XIAO Xin-Rong*,

PDF

900

被引次数

23

以(S)-2-氨基丙醇为手性源与α-溴-3-氯苯丙酮反应, (R)-2-氨基丙醇为手性源与6-甲氧基-2-(2-溴丙酰基)萘反应, 分别合成了手性纯化合物(2R,3R,5S)-3,5-二甲基-2-(3-氯苯基)-2-吗啉醇盐酸盐(4a)和(2S,3S,5R)-3,5-二甲基-2-(6-甲氧基-2-萘基)-2-吗啉醇盐酸盐(4b), 利用X射线单晶衍射仪测定了两化合物的晶体结构和两化合物的空间结构, 并初步分析两化合物空间结构, 化合物4a晶体属正交晶系, 空间群为P21212, 晶胞参数为: a＝0.8718(2) nm, b＝0.7883(2) nm, c＝2.0247(6) nm, Z＝4, V＝1.3915(7) nm3, Dc＝1.328 g/cm3, F(000)＝584, R1＝0.0399, wR2＝0.0797, S＝1.042. 化合物4b晶体属正交晶系, 空间群为P212121, 晶胞参数为: a＝0.71035 (9) nm, b＝0.77703(10) nm, c＝2.9820(4) nm, Z＝4, V＝1.6318(4) nm3, Dc＝1.318 g/cm3, F(000)＝688, R1＝0.0520, wR2＝0.1108, S＝0.994.

关键词: (S)-2-氨基丙醇, 合成, (R)-2-氨基丙醇, 手性, 吗啉醇, 晶体结构

Enantiopure compound (2R,3R,5S)-3,5-dimethyl-2-(3-chlorophenyl)-2-morpholinol hydrochloride (4a) was synthesized from (S)-2-amino-1-propanol and 2-bromo-m-chloropropiophenone, and (2S,3S,5R)-3,5- di-methyl-2-(6-methoxy-2-naphthyl)-2-morpholinol hydrochloride (4b) was from the enantioisomer (R)-2- amino-1-propanol and 6-methoxy-2-(2-bromopropionyl)naphthalene. Their crystal structures and absolute configurations were determinated by X-ray diffraction experiment and their stereo-structures were tentatively discussed. The compound 4a crystal belongs to orthorhombic system with space group P21212 and cell parameters: a＝0.8718(2) nm, b＝0.7883(2) nm, c＝2.0247(6) nm, Z＝4, V＝1.3915(7) nm3, Dc＝1.328 g/cm3, F(000)＝584, R1＝0.0399, wR2＝0.0797, S＝1.042. The compound 4b crystal belongs to ortho-rhombic system with space group P212121 and cell parame-ters: a＝0.71035 (9) nm, b＝0.77703(10) nm, c＝2.9820(4) nm, Z＝4, V＝1.6318(4) nm3, Dc＝1.318 g/cm3, F(000)＝688, R1＝0.0520, wR2＝0.1108, S＝0.994.

Key words: chiral, crystal structure, (R)-2-amino-1-propanol, synthesis, morpholinol, (S)-2-amino-1-propanol