The novel title compound（Z）-N-（4-bromo-5-ethoxy-3,5-dimethylfuran-2（5H）-yli-dene）-4-methylbenzenesulfonamide 1（C15H18BrNO4S） has been unexpectedly synthesized by the aminohalogenation reaction of ethyl 2-methy...The novel title compound（Z）-N-（4-bromo-5-ethoxy-3,5-dimethylfuran-2（5H）-yli-dene）-4-methylbenzenesulfonamide 1（C15H18BrNO4S） has been unexpectedly synthesized by the aminohalogenation reaction of ethyl 2-methylpenta-2,3-dienoate with TsNBr2,and characterized by mp,IR,1H NMR,EIMS,ESIHRMS and single-crystal X-ray diffraction.It crystallizes in mono-clinic,space group P21/c with a = 11.714（5）,b = 14.106（5）,c = 10.402（4） ,β = 97.298（8）°,V = 1704.9（12） 3,Mr = 388.27,Z = 4,Dc = 1.513 g/cm3,μ（MoKα） = 2.549 mm-1,F（000） = 792,the final R = 0.033 and wR = 0.062 for 3098 observed reflections（Ⅰ 〉 2σ（Ⅰ））.展开更多
The title compound 4-bromo-5-ethoxy-3-methyl-5-（naphthalen-l-yl）-l-tosyl-lH- pyrrol-2（5H）-one 1 （C24H22BrNO4S, Mr = 500.40） has been synthesized and its crystal structure was determined by single-crystal X-ray d...The title compound 4-bromo-5-ethoxy-3-methyl-5-（naphthalen-l-yl）-l-tosyl-lH- pyrrol-2（5H）-one 1 （C24H22BrNO4S, Mr = 500.40） has been synthesized and its crystal structure was determined by single-crystal X-ray diffraction analysis. It crystallizes in monoclinic, space group P21/n with a = 8.8562（15）, b = 18.118（3）, c = 14.055（2）A, β = 99.855（3）^o, V= 2221.9（6）A3, Z = 4, Dc = 1.496 g/cm^3,μ= 1.975 mm^-1, 2 = 0.71073A, F（000） = 1024, R = 0.0607 and wR = 0.1371.展开更多
The crystal structure of the title compound（C19H15F3N2O2,Mr = 360.33） was determined by single-crystal X-ray diffraction.The crystal belongs to triclinic,space group P1,with a = 6.5604（7）,b = 13.9614（16）,c = 18....The crystal structure of the title compound（C19H15F3N2O2,Mr = 360.33） was determined by single-crystal X-ray diffraction.The crystal belongs to triclinic,space group P1,with a = 6.5604（7）,b = 13.9614（16）,c = 18.1790（18） ,α = 102.749（7）,β = 97.542（6）,γ = 94.355（4）°,V = 1600.5（3） 3,Z = 4,Dc = 1.495 g/cm3,λ（MoKα） = 0.71070,F（000） = 744,μ（MoKα） = 0.122 mm-1,R = 0.0434 and wR = 0.1051.A total of 7590 unique reflections were collected,of which 5429 with ｜F｜2 ≥ 2σ｜F｜2 were observed.The two cyclohexene rings in the molecule adopt boat-boat conformations with the deviations of ring atoms C（9） and C10 from the C（5）/C（6）/C（7）/C（8） plane（Ⅰ） by 1.1204（0.0023） and 1.1132（0.0023） ,respectively,whereas from the C（2）/C（3）/C（5）/C（8） plane（Ⅱ） by 1.1627（0.0022） and 1.1818（0.0021） ,respectively.In the cyclopropane and lactam rings,atoms C（11） and N（1） point towards the double bond of C（9）-C（10） and the dihedral angle between the ring plane（Ⅲ） containing C（1）,C（2）,C（3） and C（4） and plane（IV） consisting of C（6）,C（7） and C（11） is 55.76（0.07）°.The dihedral angles between planes Ⅳ and Ⅰ and Ⅱ and Ⅲare 63.58（0.07）° and 58.10（0.06）°,respectively.The dihedral angle between the benzene ring C（13）～ C（18） and plane Ⅳ is 42.41（0.06）°.展开更多
In this paper, stereocontrolled tandem Michael addition-elimination reaction of the novel chiral source, S-(ι-menthyloxy)-3,4-dichloro-2(5H)-furanone, with various thiols and amines has been investigated. A series of...In this paper, stereocontrolled tandem Michael addition-elimination reaction of the novel chiral source, S-(ι-menthyloxy)-3,4-dichloro-2(5H)-furanone, with various thiols and amines has been investigated. A series of new enantiomerically pure compounds, 5-(ι-menthyloxy)-4-substituted-3-cnloro-2(5H)-furanones, were obtained in good yields with d. e.(?)98% under mild conditions.展开更多
The synthetic method of the novel chiral synthon, 5-/-menthyloxy-3-chloro-2-(5H)-furanone 5a and its application in asymmetric reactions were investigated. 5a is easily obtained in highly optical purity, and acts as a...The synthetic method of the novel chiral synthon, 5-/-menthyloxy-3-chloro-2-(5H)-furanone 5a and its application in asymmetric reactions were investigated. 5a is easily obtained in highly optical purity, and acts as a stable acceptor of Michael addition with oxygen nucleophiles in tandem double Michael addition / internal nucieophilic substitution to offer the spiro-cyclopropane derivative containing four stereogenic centers 8, which it is difficult to obtain by routine methods. The synthetic methods for 5a and 8 are reported in detail and the new compounds are identified on the basis of their analytical data and spectroscopic data, such as UV, IR, H NMR,13 C NMR, MS and elementary analysis. The absolute configuration of the interesting spiro-cyclopropanes, spiro [1-chloro-4-(/-menthyloxy)-5-oxo-6-oxa-biscyclo[3.1.0]hexane-2,3i(4’-/-menthyloxy-5’-/-menthyloxy- butyrolactone)] 8 was established by X-ray crystallography. This result can provide important synthetic strategy in synthesis of some complex展开更多
Tandem asymmetric double Michael addition/internal nucleophilic substitution of the novel chiral source, 5-(l-menthyloxy)-3-bromo-2(5H)-furanone with nucleophilic alcohol compounds has been investigated. The tandem as...Tandem asymmetric double Michael addition/internal nucleophilic substitution of the novel chiral source, 5-(l-menthyloxy)-3-bromo-2(5H)-furanone with nucleophilic alcohol compounds has been investigated. The tandem asymmetric reaction can afford four new stereogenic centers with one reaction and give optically pure spiro-cyclopropane derivatives 5a--5d which are difficult to obtain by routine methods. The synthetic method for 5a--5d was studied in detail and the new compounds were identified on the basis of their analytical data and spectroscopic data, such as [α]^(20),IR,~1H NMR,^(13)C NMR, MS and elementary analysis. The absolute configuration of the sprio [5-l-menthyloxy-3-bromo butyrolactocyclopropane-3″, 3′(4′-methyloxy-5′-menthyloxybutyrolactone)] (5a) was established by X-ray crystallography. The work can provide important synthetic strategy in synthesis of some new optically active spiro-cyclopropane analogues and some biologically active molecules with complex structure.展开更多
文摘The novel title compound（Z）-N-（4-bromo-5-ethoxy-3,5-dimethylfuran-2（5H）-yli-dene）-4-methylbenzenesulfonamide 1（C15H18BrNO4S） has been unexpectedly synthesized by the aminohalogenation reaction of ethyl 2-methylpenta-2,3-dienoate with TsNBr2,and characterized by mp,IR,1H NMR,EIMS,ESIHRMS and single-crystal X-ray diffraction.It crystallizes in mono-clinic,space group P21/c with a = 11.714（5）,b = 14.106（5）,c = 10.402（4） ,β = 97.298（8）°,V = 1704.9（12） 3,Mr = 388.27,Z = 4,Dc = 1.513 g/cm3,μ（MoKα） = 2.549 mm-1,F（000） = 792,the final R = 0.033 and wR = 0.062 for 3098 observed reflections（Ⅰ 〉 2σ（Ⅰ））.
基金This work was supported by the National Natural Science Foundation of China (No. 20472072 and 20332060)the CAS Academician Foundation of Zhejiang Province
文摘The title compound 4-bromo-5-ethoxy-3-methyl-5-（naphthalen-l-yl）-l-tosyl-lH- pyrrol-2（5H）-one 1 （C24H22BrNO4S, Mr = 500.40） has been synthesized and its crystal structure was determined by single-crystal X-ray diffraction analysis. It crystallizes in monoclinic, space group P21/n with a = 8.8562（15）, b = 18.118（3）, c = 14.055（2）A, β = 99.855（3）^o, V= 2221.9（6）A3, Z = 4, Dc = 1.496 g/cm^3,μ= 1.975 mm^-1, 2 = 0.71073A, F（000） = 1024, R = 0.0607 and wR = 0.1371.
文摘The crystal structure of the title compound（C19H15F3N2O2,Mr = 360.33） was determined by single-crystal X-ray diffraction.The crystal belongs to triclinic,space group P1,with a = 6.5604（7）,b = 13.9614（16）,c = 18.1790（18） ,α = 102.749（7）,β = 97.542（6）,γ = 94.355（4）°,V = 1600.5（3） 3,Z = 4,Dc = 1.495 g/cm3,λ（MoKα） = 0.71070,F（000） = 744,μ（MoKα） = 0.122 mm-1,R = 0.0434 and wR = 0.1051.A total of 7590 unique reflections were collected,of which 5429 with ｜F｜2 ≥ 2σ｜F｜2 were observed.The two cyclohexene rings in the molecule adopt boat-boat conformations with the deviations of ring atoms C（9） and C10 from the C（5）/C（6）/C（7）/C（8） plane（Ⅰ） by 1.1204（0.0023） and 1.1132（0.0023） ,respectively,whereas from the C（2）/C（3）/C（5）/C（8） plane（Ⅱ） by 1.1627（0.0022） and 1.1818（0.0021） ,respectively.In the cyclopropane and lactam rings,atoms C（11） and N（1） point towards the double bond of C（9）-C（10） and the dihedral angle between the ring plane（Ⅲ） containing C（1）,C（2）,C（3） and C（4） and plane（IV） consisting of C（6）,C（7） and C（11） is 55.76（0.07）°.The dihedral angles between planes Ⅳ and Ⅰ and Ⅱ and Ⅲare 63.58（0.07）° and 58.10（0.06）°,respectively.The dihedral angle between the benzene ring C（13）～ C（18） and plane Ⅳ is 42.41（0.06）°.
基金Project (No. 29132036) supported by the National Natural Science Foundation of China
文摘In this paper, stereocontrolled tandem Michael addition-elimination reaction of the novel chiral source, S-(ι-menthyloxy)-3,4-dichloro-2(5H)-furanone, with various thiols and amines has been investigated. A series of new enantiomerically pure compounds, 5-(ι-menthyloxy)-4-substituted-3-cnloro-2(5H)-furanones, were obtained in good yields with d. e.(?)98% under mild conditions.
文摘The synthetic method of the novel chiral synthon, 5-/-menthyloxy-3-chloro-2-(5H)-furanone 5a and its application in asymmetric reactions were investigated. 5a is easily obtained in highly optical purity, and acts as a stable acceptor of Michael addition with oxygen nucleophiles in tandem double Michael addition / internal nucieophilic substitution to offer the spiro-cyclopropane derivative containing four stereogenic centers 8, which it is difficult to obtain by routine methods. The synthetic methods for 5a and 8 are reported in detail and the new compounds are identified on the basis of their analytical data and spectroscopic data, such as UV, IR, H NMR,13 C NMR, MS and elementary analysis. The absolute configuration of the interesting spiro-cyclopropanes, spiro [1-chloro-4-(/-menthyloxy)-5-oxo-6-oxa-biscyclo[3.1.0]hexane-2,3i(4’-/-menthyloxy-5’-/-menthyloxy- butyrolactone)] 8 was established by X-ray crystallography. This result can provide important synthetic strategy in synthesis of some complex
基金Project supported by the National Natural Science Foundation of China (Grant No. 29672004)
文摘Tandem asymmetric double Michael addition/internal nucleophilic substitution of the novel chiral source, 5-(l-menthyloxy)-3-bromo-2(5H)-furanone with nucleophilic alcohol compounds has been investigated. The tandem asymmetric reaction can afford four new stereogenic centers with one reaction and give optically pure spiro-cyclopropane derivatives 5a--5d which are difficult to obtain by routine methods. The synthetic method for 5a--5d was studied in detail and the new compounds were identified on the basis of their analytical data and spectroscopic data, such as [α]^(20),IR,~1H NMR,^(13)C NMR, MS and elementary analysis. The absolute configuration of the sprio [5-l-menthyloxy-3-bromo butyrolactocyclopropane-3″, 3′(4′-methyloxy-5′-menthyloxybutyrolactone)] (5a) was established by X-ray crystallography. The work can provide important synthetic strategy in synthesis of some new optically active spiro-cyclopropane analogues and some biologically active molecules with complex structure.
