北京大学学报(自然科学版)

(R)-2-羟甲基-1-氮杂-4-硫杂螺[4.5]癸烷的合成及晶体结构

王辉,裴伟伟,章士伟,孙国斌   

  1. 北京大学化学与分子工程学院,北京,100871
  • 收稿日期:2003-11-28 出版日期:2004-11-20 发布日期:2004-11-20

Synthesis and Crystal Structure of(R)-2-Hydroxymethyl-1-aza-4-thiaspiro[4.5]decane

WANG Hui, PEI Weiwei, ZHANG Shiwei, SUN Guobin   

  1. College of Chemistry and Molecular Engineering, Beijing 100871
  • Received:2003-11-28 Online:2004-11-20 Published:2004-11-20

摘要: 合成了标题化合物C9H17NOS,它的晶体结构已经用X-射线单晶衍射法测定。晶体属正交晶系,P212121空间群,晶胞参数a=0.6704(1)nm,b=0.8167(2)nm,c=1.8267(4)nm,V=1.0000 (3)nm3Z=4,Mr=187.30,Dc=1.244 g/cm3F(000)=408,μ (MoKα)=0.279 mm-1。晶体结构用直接法解出,经全矩阵最小二乘法对原子参数进行修正,最终的偏离因子为R=0.0295,wR=0.0642。结构测定表明标题化合物是单螺化合物。由C(1)、C(2)、C(3)、C(4)、C(5) 和C(6) 构成的六元环取椅型构象, 由C(1)、S、C(7)、C(8) 和N构成的五元环取半椅型构象, 两个环共用的螺原子C(1)用sp3杂化轨道与其他原子成键。晶体结构分析表明存在着分子间氢键。

关键词: (R)-2-羟甲基-1-氮杂-4-硫杂螺[4.5]癸烷, 合成, 晶体结构, 手性催化剂, 分子间氢键

Abstract: The title compound C9H17NOS was synthesized and its crystal structure was determined by single crystal X-ray diffraction. The crystal is orthorhombic system, space group P212121 with parameters a=0.670 4(1) nm, b=0.816 7(2) nm,c=1.826 7(4) nm, V=1.000 0(3) nm3, Z=4, Mr=187.30, Dc=1.244 g/cm3, F(000)=408, μ(MoKα)=0.279 mm-1. The structure was solved by direct met hods and refined by full matrix least squares to the final R=0.029 5, wR=0.064 2. X-ray analysis reveals that the compound is a single spiral compound. The six-membered ring which is composed of C (1), C (2), C (3), C (4), C (5), and C (6) is chair conformatio n. The fivemembered ring which is composed of C (1), S, C (7), C (8), and N is half-chair conformation. Crystal structural analysis shows that intermolecular hydrogen bonds occur between hydroxyl group and nitrogen atom.

Key words: (R)-2-hydroxymethyl-1-aza-4-thiaspiro[4.5]decane, synthesis, crystal structure, chiral ligand, intermolecular hydrogen bond

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