Synthesis and Crystal Structures of 2-Azido-4-aminocyclohexane-1,3-diols

被引:1
|
作者
Brennan, Meabh B. [1 ]
Davies, Stephen G. [1 ]
Lee, James A. [1 ]
Thompson, Amber L. [1 ]
Thomson, James E. [1 ]
机构
[1] Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England
关键词
Amino alcohol; Hydrogen bonding; Epoxide ring-opening; Regioselectivity; DIASTEREOSELECTIVE OLEFINIC OXIDATION; X-RAY-DIFFRACTION; ALLYLIC AMINES; HOMOALLYLIC AMINES; EPOXIDATION; CYCLOPROPANATION; DIHYDROXYLATION; PROTOCOL;
D O I
10.1007/s10870-015-0607-x
中图分类号
O7 [晶体学];
学科分类号
0702 ; 070205 ; 0703 ; 080501 ;
摘要
2-Azido-4-aminocyclohexane-1,3-diols 12, 14 and 16 were synthesised and their crystal structures were studied by X-ray diffraction. Compound 12 crystallizes in the monoclinic space group P2 (1) /n with cell parameters of a = 13.7059(2) , b = 10.8861(2) , c = 13.8675(3) , beta = 117.2365(10)A degrees, V = 1839.67(6) (3) and Z = 4. Compound 14 crystallizes in the orthorhombic space group Pcab with cell parameters of a = 9.9508(1) , b = 10.9839(2) , c = 24.7035(4) , V = 2700.06(7) (3) and Z = 8. Compound 16 crystallizes in the triclinic space group with cell parameters of a = 10.9511(3) , b = 11.3148(3) , c = 15.9545(5) , alpha = 86.3487(11)A degrees, beta = 87.4723(11)A degrees, gamma = 89.3398(10)A degrees, V = 1970.91(10) (3) and Z = 4. All three structures were characterised by arrays of hydrogen bonding interactions and these crystallographic studies also revealed their conformations, which gave valuable information into the regioselectivity of epoxide ring-opening during their formation. Three 2-azido-4-aminocyclohexane-1,3-diols 12, 14 and 16 were synthesised and their crystal structures were studied by X-ray diffraction. All three structures were characterised by arrays of hydrogen bonding interactions and these crystallographic studies also revealed valuable conformational data which was used to rationalise the regioselectivity of epoxide ring-opening during their formation. [GRAPHICS] .
引用
收藏
页码:401 / 409
页数:9
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