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(E)-5-苯基-5-对甲苯基-4-对甲苯磺酰基-1,4-戊二烯的合成、表征及其晶体结构 被引量：1

Synthesis and Crystal Structure of (E)-5-Phenyl-5-(p-Tolyl)-4-(p-Tolylsulfonyl)-1,4-Pentadiene
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摘要 通过氰化亚铜催化下对甲苯基溴化镁与1-苯基-2-对甲苯磺酰基乙炔的碳镁化反应及其进一步与烯丙基溴的偶联反应,得到了(E)-5-苯基-5-对甲苯基-4-对甲苯磺酰基-1,4-戊二烯.产物经1H NMR,IR,MS和元素分析表征,其晶体结构经X-射线单晶衍射分析确证.晶体属单斜晶系,空间群P2(1)/n,晶胞参数:a=5.9754(5),b=22.733(2),c=15.3656(3);α=90°,β=92.512°,γ=90°;V=2085.1(3)3,T=293K,Z=4,Dc=1.238g/cm3,μ=0.173mm-1,λ=0.71073,F(000)=824,结构偏离因子R=0.0545,wR=0.1176,共收集到12695个独立衍射点,其中I>2σ(I)的可观测点为4060个.晶体结构分析表明标题化合物为E型结构. The title compound （E） - 5- phenyl- 5- （p - tolyl） -4- （p - tolylsulfonyl） - 1, 4- pentadiene was synthesized by the reaction of 2 - phenyl - 1 - （ p - tolylsulfonyl）ethyne, p - tolylmagnesium bromide and allyl bromide. The compound was characterized by t H NMR, IR, MS and elemental analysis. The single crystal structure was determined by X-ray diffraction analysis. Crystal crystallizes in monoclinic, space group P2（1）/n with unit cell parameters： a = 5. 9754（5）, b = 22. 733（2）, c = 15. 3656（ 13）A^°; α = 90°, β = 92. 512°,γ=90°;V=2085. 1（3）A^°3,T=293 K,Z=4, Dc = 1.238 g/cm^3,μ=0. 173 mm^-1 ,λ= 0. 71073A^°,F（000） =824. The final R = 0. 0545, wR= 0. 1176, 12695 independent were collected, of which 4772 independent reflections with Ⅰ 〉2a（Ⅰ） were used. The molecular structure shows the configuration of the title compound is in E-fashion.
作者 谢美华 孙应 谷晓霞 赵新阳 张伟 谢发东
机构地区 安徽师范大学化学与材料科学学院
出处 《安徽师范大学学报（自然科学版）》 CAS 2008年第1期45-48,共4页 Journal of Anhui Normal University(Natural Science)
基金 国家自然科学基金(20672001) 安徽省教育厅(TD200707)资助
关键词 对甲苯基溴化镁 碳镁化反应 1 4-戊二烯 晶体结构 p-tolylmagnesium bromide carbomagnesiation 1, 4 - pentadiene crystal structure
分类号 O625.73 [理学—有机化学]
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参考文献9

  • 1FLEMING F F, GUDIPATI V, STEWARD O W. Alkynenitriles: Chelating-controlled conjugate additions[J]. Org Lett, 2002, 4: 659.
  • 2ZHU N, HALL D G. Effect of additives on the stereochemical integrity and reactivity of a-alkoxycarbonyl alkenylcopper intermediates. Optimal conditions for the synthesis of isomerically pure tetrasubstituted alkenes[J]. J Org Chem, 2003, 68: 6066.
  • 3Flavranek M, Dvorak D. 3,3-disubstituted allyl alcohols from palladium-catalyzed coupling of hydroaluminated propargyl alcohols with aryl iodides[J]. J Org Chem, 2002, 67: 2125.
  • 4SHIRAKAWA E, YAMAGAMI T, KIMURA T, YAMAGUCHI S, HAYASHI T. Arylmagnesiation of alkynes catalyzed cooperatively by iron and copper complexes[J]. J Am Chem Soc, 2005, 127: 17164.
  • 5MATSUKAWA Y, ASAO N, KITAHARA H, YAMAMOTO Y. Lewis acid catalyzed allylstannylation of unactivated alkynes [J]. Tetrahedron, 1999, 55: 3779.
  • 6KABALKA G W, AI-Masum M. Microwave-enhanced palladium-catalyzed cross-coupling reactions of potassium vinyltrifluoroborates and allyl acetates: A New Route to 1, 4-Pentadienes[J]. Org Lett, 2006, 8: 11.
  • 7XIE M H, WANG J L, GU X X, SUN Y, WANG S W. Highly regio- and stereoselective synthesis of tetrasubstituted olefins by three- component tandem reaction of allylzinc bromide, acetylenic sulfone and halohydrocarbon[J]. Org Lett,2006, 8: 431.
  • 8XIE M H, LIU L, WANG J L, WANG S W. Stereoselective synthesis of vinyl sulfones by carbomagnesiation of acetylenic sulfone in the presence of CuCN[J]. J Organomet Chem, 2005, 690: 4058.
  • 9谢美华,刘莉.1,1-二苯基-2-对甲苯砜基乙烯的合成及其晶体结构[J].安徽师范大学学报（自然科学版）,2004,27(1):49-51. 被引量：3

二级参考文献13

  • 1Fuchs P L, Braish T F. Multiply convergent synthesis via conjugate- addition reactions to cycloalkenyl sulfones[J]. Chem Rev, 1986, 86:903.
  • 2Simpkin N S. The chemistry of vinyl sulphones[J]. Tetrahedron, 1990, 46: 6951.
  • 3NáJera C, Yus M. Desulfonylation reactions: recent developments [J]. Tetrahedron, 1999, 55: 10547.
  • 4Popoff I C, Denver J L. α,β - Unsaturated sulfones via phosphonate carbaniom[J]. J Org Chem, 1969, 34:1128.
  • 5Gancarz R A, Kice J L. Photodecornposition of selenosulfonates and their facile photoaddition to alkenes [J]. Tetrahedron Lett, 1980, 21:
  • 6Back T G, Collins S, Kerr R G. Selenosulfonation of acetylene: preparation of novel β - (phenylseleno)vinyl sulfones and their conversion to acetylenic and β - functionalized sulfones[J]. J Org Chem, 1983, 48:3077.
  • 7Müller V J, Neuburger M, Zehnder M. 1 - Lithio- 2, 2 - diphenyl - 1 - (phenylsulfonyl)ethen: Synthese und Kristallstruktur[J]. Helve Chim Acta, 1995, 78: 615.
  • 8Smorada R L, Truce W E. Reactions of arylsulfonylacetylenes with organolithium and Grignards: a new synthesis of acetylenes[J]. J Org Chem, 1979, 44:3444.
  • 9Truce W E, Wolf G C. Adducts of sulfonyl iodides with acetylenes[J]. J Org Chem, 1971, 36:1727.
  • 10Gancarz R A, Kite J L. Se- phenyl areneselenosulfonatea: their facile formation and striking chemistry[J]. J Org Chem, 1981, 46: 4899.

共引文献2

同被引文献14

  • 1TRUCE W E,WOLF G C. Adducts of sulfonyl iodides with acetylenes[J ]. J Org Chem, 1971,36 (13) : 1727 - 1732.
  • 2ITAMI, K, KAMEI T, YOSHIDA J. Diversity-oriented synthesis of tamoxifen-type tetrasubstituted olefins[J]. J Am Chem Soc, 2003, 125 (48):14670 -14671.
  • 3TESSIER P E, PENWELL A J, SOUZA F E S, FALLIS A G. (Z)-tamoxifen and tetrasubstituted alkenes and dienes via a regio- and stereospecific three-component magnesium carhometalation palladium(O) cross-coupling strategy[J]. Org Lett,2003,5(17):2989- 2992.
  • 4CATURLA F,AMAT M,REINOSO R F,CORDOBA M. WARRELLOW G. Racemic and chiral sulfoxides as potential proclrugs of the COX-2 inhibitors Vioxx and Arcoxia [J]. Bioorg Med Chem Lett,2006,16(12):3209-3212.
  • 5LEMAY A B, VULIC K S, OGILVIE W W. Single-isomer tetra.substituted olefins from regioselective and stereospecific palladium-catalyzed coupling of β-chloro-iodo-α,β-unsaturated esters[J]. J Org Chem,2006,71 (9) :3615 -3618.
  • 6HAYASHI T, YAMASAKI K. Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions[J]. Chem Rev,2093,103(8) :2829 - 2844.
  • 7KANEMURA S, KONDOH A, YORIMITSU H, OSHIMA K. Carbocupration of 1-2829 - 2844.
  • 8KANEMURA S, KONDOH A, YORIMITSU H, OSHIMA K. Carbocupration of 1-alkynylphosphines followed by trapping with electrophiles [J]. OrgLett,2007,9(10):2031 - 2033.
  • 9MULLER A J ,JENNINGS M P. A highly stereoselective TMSOTf-mediated catalytic carbocupration of alkynoates[J]. Org Lett,2007,9(25) :5327 - 5329.
  • 10LU Z, MA S M. Studies on the Cu( I)-catalyzed regioselective anti-carbometallation of secondary terminal propargylic alcohols[J]. J Org Chem,2006,71(7):2655 - 2660.

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安徽师范大学学报（自然科学版）
2008年 第1期

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