3-(3,4-亚甲二氧基)苯基-6-孟氧基-6,6a-二氢-呋喃并[3,4-d]异噁唑啉-4(3aH)-酮的合成和晶体结构

标题化合物是由5-(R)-(l-孟氧基)-2(5H)-呋喃酮与3,4-亚甲二氧基苯甲醛肟在次氯酸钙作为氧化剂的条件下,进行的区域选择性原位1,3-偶极环加成反应得到。结构通过单晶X-射线衍射法确定, C22H27NO6其晶体属正交晶系, 空间群为P212121, Mr = 401.45, a = 6.2600(3), b = 10.7300(11), c = 31.2160(25) , V = 2096.8(3) 3, Z = 4, Dc = 1.272 g/cm3, μ = 0.09 mm-1, F(000) = 856。最终的可靠因子为R f = 0.073, wR = 0.186。在分子结构中,平面1(异噁唑啉环)与平面2(呋喃酮环)之间的二面角为67.4°, 孟氧基中的环己烷环为椅式构象,呋喃酮并异噁唑啉环上的3个手性中心的构型为SC3a, RC6, RC6a。

Synthesis and Crystal Structure of 3-(3,4-Methylenedioxy)phenyl-6- menthyloxy-6,6a-dihydro-furo[3,4-d]isoxazol-4(3aH)-one

The title compound (C22H27O6N) has been synthesized by in situ regioselective 1,3-dipolar cyclo- addition of 3,4-methylenedioxybenzaldoxime to 5-(R)-(l-menthyloxy)-2(5H)-furanone by using calcium hypochlorite as oxidant and its structure was determined by single-crystal X-ray diffraction. The crystal belongs to orthorhombic, space group P212121 with a = 6.2600(3), b = 10.7300(11), c = 31.2160(25) , V = 2096.8(3) 3, Z = 4, Mr = 401.45, Dc = 1.272 g/cm3, μ = 0.09 mm-1 and F(000) = 856. The structure was solved by direct methods and refined by block-matrix least-squares techniques to the final Rf = 0.073 and wR = 0.186. X-ray diffraction analysis reveals that the dihedral angle between planes 1 (isoxazoline) and 2 (furanone) is 67.4°; the furanone ring is of envelope conformation and the configurations of three chiral carbon atoms in furoisoxazoline are SC3a, RC6 and RC6a, respectively.