Synthesis and Crystal Structure of 5(R)-(1R,2S,5R)-Menthoxy-4(R)-N-cyclohexylaminobutyrolactone

摘要

The title compound, 5(R)-(1R,2S,5R)-menthoxy-4(R)-N-cyclohexylaminobutyrolactone 1, has been synthesized via the asymmetric Micheal addition reaction of 5(R)-menthoxy-2(5H)-furanone 4 with cyclohexylamine 5, and structurally determined by single-crystal X-ray diffraction. Crystal data: C20H36NO3, Mr = 337.49, monoclinic system, space group P21, a = 9.8677(7),b = 9.7737(7), c = 11.0204(8)(A),β= 103:7820(10)°, V= 1032.25(13)(A)3,Z = 2, Dc= 1.086 g/cm3,λ(MoKα) = 0.071073 nm, μ= 0.071 mm-1 and F(000) = 372. The structure was refined to R =0.0328 and wR = 0.0864 for 4203 observed reflections (I＞2σ(I)). The crystallographic results of molecule 1 show that the functionalized N-cyclohexylamino group is linked in the 4-position of butyrolactone to form the novel chiral optically active compound.