2-Dimethylsulfuranyliden-1-(3-nitro-phenyl)-aethanon

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Dimethylsulfuranyliden-1-(3-nitro-phenyl)-aethanon
• 英文别名: 2-(Dimethyl-lambda4-sulfanylidene)-1-(3-nitrophenyl)ethanone；2-(dimethyl-λ4-sulfanylidene)-1-(3-nitrophenyl)ethanone
• 化学式: C₁₀H₁₁NO₃S
• 分子量: 225.268
• InChiKey: RKEXEWQQSHGTQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Dimethylsulfuranyliden-1-(3-nitro-phenyl)-aethanon 在 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-(3-(3-nitrophenyl)-3-oxopropyl)-4,6-diphenyl-3,4-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  手性N-杂环卡宾催化的查耳酮与甲酰基环丙烷的正式Diels-Alder反应

  摘要：

  揭示了查耳酮与甲酰基环丙烷之间的高度对映选择性（形式）杂狄尔斯-阿尔德反应。来自甲酰基环丙烷的具有挑战性的N-杂环卡宾（NHC）结合的烯酸酯中间体被捕获用于新的C-C键形成反应。获得具有高非对映异构体和对映异构体选择性的反应产物，并且可以容易地将其转化为光学纯的多取代的环己烷衍生物。

  DOI：

  10.1021/ol202250s
• 作为产物：
  描述：

  dimethyl(2-(3-nitrophenyl)-2-oxoethyl)sulfonium bromide 在 sodium hydroxide 作用下， 以 水 为溶剂， 以0.168 g的产率得到2-Dimethylsulfuranyliden-1-(3-nitro-phenyl)-aethanon
  参考文献：
  名称：

  Synthesis and characterization of novel simultaneous C and O-coordinated and nitrate-bridged complexes of silver(i) with carbonyl-stabilized sulfonium ylides and their antibacterial activities

  摘要：

  二甲基硫onium ylides (Me)2SCHC(O)C6H4R (R = H; m-NO2; p-NO2; p-OMe; p-Me 和 p-Br) 与AgNO3在二氯甲烷中的反应生成了多种化合物。单晶X射线衍射分析表明，所得加合物有三种形态：(i) 二维聚合物 [AgNO3(Me2SCHC(O)C6H5)]n (1)，其中硝酸盐桥接，每个硝酸盐通过两个氧原子与三个银原子配位，且两个Me2SCHC(O)C6H5配体通过碳原子与银中心配位；(ii) 阳离子双核 [Ag(Me2SCHC(O)C6H4-m-NO2)2]2(NO3)2·2H2O (2)，在此中，Me2SCHC(O)C6H4-m-NO2配体同时通过碳和氧原子配位，硝酸盐作为对离子；(iii) 阳离子单核和阴离子双核 [Ag(Me2SCHC(O)C6H4-p-NO2)2]2[{AgNO3(μ-NO3)(Me2SCHC(O)C6H4-p-NO2)}2]·2CH3OH (3)，其中硝酸根作为桥接和末端配体，Me2SCHC(O)C6H4-p-NO2配体表现出C配位。通过红外光谱、1H和13C-NMR光谱对获得的化合物进行了表征，分析数据显示银(I)硝酸盐与ylide p-OMe (4)之间呈1:2的化学计量，而ylides p-Me (5)和p-Br (6)之间为1:1。此外，通过琼脂扩散法评估了化合物1–6在DMSO溶液中的抗菌效果，针对三种革兰阳性和三种革兰阴性细菌进行了测试。所有复合物对这些细菌均表现出抗菌活性，对革兰阴性菌的抑制效力较高。

  DOI：

  10.1039/c2dt31902k

文献信息

• Enantioselective Synthesis of Dihydropyrazoles by Formal [4+1] Cycloaddition of in Situ-Derived Azoalkenes and Sulfur Ylides
  作者：Jia-Rong Chen、Wan-Rong Dong、Mathieu Candy、Fang-Fang Pan、Manuel Jörres、Carsten Bolm

  DOI：10.1021/ja301196x

  日期：2012.4.25

  An unprecedented strategy to access highly enantioenriched dihydropyrazoles is described. It involves formal [4+1] cycloadditions of in situ-derived azoalkenes and sulfur ylides catalyzed by a chiral copper/Tol-BINAP complex. A variety of synthetically and biologically important dihydropyrazoles have been obtained with high enantioselectivities (up to 97:3 er) in good yields (83-97%).

  描述了一种前所未有的获得高度对映体富集的二氢吡唑的策略。它涉及由手性铜/Tol-BINAP配合物催化的原位衍生的偶氮烯烃和硫叶立德的正式[4+1]环加成。已经以高对映选择性（高达 97:3 er）以良好的产率（83-97%）获得了多种合成和生物学上重要的二氢吡唑。
• Synthesis of Indoles through Highly Efficient Cascade Reactions of Sulfur Ylides and N-(ortho-Chloromethyl)aryl Amides
  作者：Qing-Qing Yang、Cong Xiao、Liang-Qiu Lu、Jing An、Fen Tan、Bin-Jie Li、Wen-Jing Xiao

  DOI：10.1002/anie.201203657

  日期：2012.9.3

  Batting the ylides: A simple procedure carried out under mild conditions allows the direct and efficient synthesis of structurally diverse indoles. This approach involves a cascade reaction of sulfur ylides and N‐(ortho‐chloromethyl)aryl amides (see scheme).

  击球叶立德：一个简单的程序在温和的条件下进行允许结构不同的吲哚的直接和有效的合成。这种方法涉及硫叶立德和的级联反应ñ - （邻氯甲基）芳基酰胺（参见方案）。
• New Pd(<scp>ii</scp>) complexes of sulfur ylides; synthesis, X-ray characterization, a theoretical study and catalytic activity toward the Mizoroki–Heck reaction
  作者：S. J. Sabounchei、M. Ahmadianpoor、A. Yousefi、A. Hashemi、M. Bayat、A. Sedghi、F. Akhlaghi Bagherjeri、R. W. Gable

  DOI：10.1039/c6ra01390b

  日期：——

  structure of complex trans-[PdCl2(SMe2C(H)C(O)C6H4-p-NO2)2] (3) was characterized by single crystal X-ray analysis. The X-ray crystallography results reveal that the structure of complex 3 contains two Cα-coordinated sulfur ylide ligands in trans geometry. These air/moisture stable complexes were also employed as efficient catalysts for the Mizoroki–Heck cross-coupling reaction of several aryl halides with

  硫化氢（L）SMe 2 C（H）C（O）R（R = 4-硝基苯基，苯基和3-硝基苯基）与二氯（1,5-环辛二烯）钯（II）络合物的反应[的PdCl 2（COD）]，以2：1的比例给出了新的Pd（II）型的复合体的顺式-和反式- [的PdCl 2（SME 2 C（H）C（O）R）2 ]（R =苯基（1），3-硝基苯基（2）和4-硝基苯基（3））。通过元素分析，IR，1 H，13 C NMR和质谱对得到的配合物进行表征。而且，结构复杂通过单晶X射线分析对反式-[PdCl 2（SMe 2 C（H）C（O）C 6 H 4 - p -NO 2）2 ]（3）进行表征。X射线晶体学结果表明，配合物3的结构在反式中包含两个Cα配位的硫叶立德配体。几何学。这些对空气/水分稳定的络合物也被用作几种芳基卤化物与烯烃的Mizoroki-Heck交叉偶联反应的有效催化剂。这些反应的偶联产物以良好至优异的产率和纯度，
• Formal Diels–Alder Reactions of Chalcones and Formylcyclopropanes Catalyzed by Chiral N-Heterocyclic Carbenes
  作者：Hui Lv、Junming Mo、Xinqiang Fang、Yonggui Robin Chi

  DOI：10.1021/ol202250s

  日期：2011.10.7

  Highly enantioselective (formal) hetero-Diels–Alder reactions between chalcones and formylcyclopropanes are disclosed. The challenging N-heterocyclic carbene (NHC)-bounded enolate intermediates from formylcyclopropanes were captured for new C–C bond forming reactions. The reaction products were obtained with high diastereo- and enantioselectivities and could be easily transformed to optically pure

  揭示了查耳酮与甲酰基环丙烷之间的高度对映选择性（形式）杂狄尔斯-阿尔德反应。来自甲酰基环丙烷的具有挑战性的N-杂环卡宾（NHC）结合的烯酸酯中间体被捕获用于新的C-C键形成反应。获得具有高非对映异构体和对映异构体选择性的反应产物，并且可以容易地将其转化为光学纯的多取代的环己烷衍生物。
• Synthesis and characterization of novel simultaneous C and O-coordinated and nitrate-bridged complexes of silver(<scp>i</scp>) with carbonyl-stabilized sulfonium ylides and their antibacterial activities
  作者：Seyyed Javad Sabounchei、Fateme Akhlaghi Bagherjeri、Zeinab Mozafari、Colette Boskovic、Robert W. Gable、Roya Karamian、Mostafa Asadbegy

  DOI：10.1039/c2dt31902k

  日期：——

  Reaction of sulfonium ylides (Me)2SCHC(O)C6H4R (R = H; m-NO2; p-NO2; p-OMe; p-Me and p-Br) with AgNO3 in dichloromethane leads to various compounds. Single crystal X-ray diffraction analysis reveals that the adducts take 3 forms: (i) two-dimensional polymer, [AgNO3(Me2SCHC(O)C6H5)]n (1), with nitrate bridges in which each nitrate coordinates to three silver atoms through two oxygen atoms and two Me2SCHC(O)C6H5 ligands coordinate to silver centers through carbon atoms; (ii) cationic binuclear, [Ag(Me2SCHC(O)C6H4-m-NO2)2]2(NO3)2·2H2O (2), in which Me2SCHC(O)C6H4-m-NO2 ligands simultaneously coordinate through both carbon and oxygen atoms with nitrate as a counter ion, and (iii) cationic mononuclear and anionic binuclear, [Ag(Me2SCHC(O)C6H4-p-NO2)2]2[AgNO3(μ-NO3) (Me2SCHC(O)C6H4-p-NO2)}2]·2CH3OH (3), in which nitrate groups act as bridging as well as terminal ligands, and Me2SCHC(O)C6H4-p-NO2 ligands display C-coordination. Characterization of the obtained compounds was also performed by infrared, 1H- and 13C-NMR spectroscopy and analytical data indicated a 1 : 2 stoichiometry between the silver(I) nitrate and ylide p-OMe (4) and 1 : 1 for ylides p-Me (5) and p-Br (6). In addition, the antibacterial effects of DMSO-solutions of complexes 1–6 were evaluated by the agar disc diffusion method against three Gram positive and three Gram negative bacteria. All complexes displayed antibacterial activity against these bacteria, with high levels of inhibitory potency exhibited against the Gram negative species.

  二甲基硫onium ylides (Me)2SCHC(O)C6H4R (R = H; m-NO2; p-NO2; p-OMe; p-Me 和 p-Br) 与AgNO3在二氯甲烷中的反应生成了多种化合物。单晶X射线衍射分析表明，所得加合物有三种形态：(i) 二维聚合物 [AgNO3(Me2SCHC(O)C6H5)]n (1)，其中硝酸盐桥接，每个硝酸盐通过两个氧原子与三个银原子配位，且两个Me2SCHC(O)C6H5配体通过碳原子与银中心配位；(ii) 阳离子双核 [Ag(Me2SCHC(O)C6H4-m-NO2)2]2(NO3)2·2H2O (2)，在此中，Me2SCHC(O)C6H4-m-NO2配体同时通过碳和氧原子配位，硝酸盐作为对离子；(iii) 阳离子单核和阴离子双核 [Ag(Me2SCHC(O)C6H4-p-NO2)2]2[AgNO3(μ-NO3)(Me2SCHC(O)C6H4-p-NO2)}2]·2CH3OH (3)，其中硝酸根作为桥接和末端配体，Me2SCHC(O)C6H4-p-NO2配体表现出C配位。通过红外光谱、1H和13C-NMR光谱对获得的化合物进行了表征，分析数据显示银(I)硝酸盐与ylide p-OMe (4)之间呈1:2的化学计量，而ylides p-Me (5)和p-Br (6)之间为1:1。此外，通过琼脂扩散法评估了化合物1–6在DMSO溶液中的抗菌效果，针对三种革兰阳性和三种革兰阴性细菌进行了测试。所有复合物对这些细菌均表现出抗菌活性，对革兰阴性菌的抑制效力较高。