| Synthesis and Crystal Structure of Spiro[1-bromo-4-l-menthyloxy-5-oxo-6-oxa-bicyclo[3.1.0]hexane-2,2'-3'-(16'-methoxyacetatyl-4'-l-menthyloxybutyrolactone)] |
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| 作者姓名： | 郭金波 王建革 史泉水 陈庆华 |
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| 作者单位： | Department of Chemistry Luoyang Normal College，Department of Chemistry，Luoyang Normal College，Department of Chemistry，Luoyang Normal College，Department of Chemistry，Luoyang Normal College，Luoyang 471022，China，Luoyang 471022，China，Luoyang 471022，China，Luoyang 471022，China |
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| 摘 要： | The title compound,spiro1-bromo-4-l-menthyloxy-5-oxo-6-oxa-bicyclo3.1.0]-hexane-2,2'-3'-(16'-methoxyacetatyl-4'-l-menthyloxybutyrolactone)] 1,was obtained via tandem asymmetric double Michael addition/internal nucleophilic substitution of the chiral synthon,5-l-menthyloxy-3-bromo-2-(5H)-furanone 2 with methoxy α-chloroacetate as a nucleophile under mild conditions,and structurally determined by single-crystal X-ray diffraction.Crystal data:C31H47BrO9,Mr = 643.60,orthorhombic,space group P212121,a = 9.6564(7),b = 14.8994(11),c =23.6771(17) (A),V= 3406.5(4) (A)3,Z= 4,Dc= 1.255 g/cm3,λ(MoKα) = 0.71073(A),μ= 1.254 mm-1and F(000) = 1360.The structure was refined to R =0.0324 and wR = 0.0737 for 5123 observed reflections (I ＞ 2σ(I)).The crystallographic results of molecule 1 show that the interesting reaction of 2 with methoxy α-chloroacetate,in the usual manner,gave the spiro-cyclopropane skeleton with O-linked derivative containing multiple stereogenic centers 1 rather than the expected C-linked derivative.
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Synthesis and Crystal Structure of Spiro[1-bromo-4-l-menthyloxy-5-oxo-6-oxa-bicyclo [3.1.0] hexane-2,2'-3'-(16'-methoxyacetatyl-4'-l-menthyloxybutyrolactone)] |
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| GUO Jin-Bo,WANG Jian-Ge,SHI Quan-Shui,CHEN Qing-Hua.Synthesis and Crystal Structure of Spiro[1-bromo-4-l-menthyloxy-5-oxo-6-oxa-bicyclo[3.1.0]hexane-2,2'-3'-(16'-methoxyacetatyl-4'-l-menthyloxybutyrolactone)][J].Chinese Journal of Structural Chemistry,2007,26(1). |
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| Authors: | GUO Jin-Bo WANG Jian-Ge SHI Quan-Shui CHEN Qing-Hua |
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| Abstract: | The title compound,spiro1-bromo-4-l-menthyloxy-5-oxo-6-oxa-bicyclo3.1.0]-hexane-2,2'-3'-(16'-methoxyacetatyl-4'-l-menthyloxybutyrolactone)] 1,was obtained via tandem asymmetric double Michael addition/internal nucleophilic substitution of the chiral synthon,5-l-menthyloxy-3-bromo-2-(5H)-furanone 2 with methoxy α-chloroacetate as a nucleophile under mild conditions,and structurally determined by single-crystal X-ray diffraction.Crystal data:C31H47BrO9,Mr = 643.60,orthorhombic,space group P212121,a = 9.6564(7),b = 14.8994(11),c =23.6771(17) (A),V= 3406.5(4) (A)3,Z= 4,Dc= 1.255 g/cm3,λ(MoKα) = 0.71073(A),μ= 1.254 mm-1and F(000) = 1360.The structure was refined to R =0.0324 and wR = 0.0737 for 5123 observed reflections (I ＞ 2σ(I)).The crystallographic results of molecule 1 show that the interesting reaction of 2 with methoxy α-chloroacetate,in the usual manner,gave the spiro-cyclopropane skeleton with O-linked derivative containing multiple stereogenic centers 1 rather than the expected C-linked derivative. |
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| Keywords: | chiral spiro-cyclopropane skeleton with O-linked derivative asymmetric tandem reaction optically active molecule X-ray crystallography Spiro Crystal Structure skeleton containing multiple rather expected derivative manner crystallographic results molecule show interesting reaction structure refined space group data |
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