5-((N,N-dimethyl-4-aminophenyl)metyhyl)-2,3,4,5-tetrahydro-2-furanone

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-((N,N-dimethyl-4-aminophenyl)metyhyl)-2,3,4,5-tetrahydro-2-furanone
• 英文别名: 5-(N,N-dimethyl-4-aminobenzyl)-2,3,4,5-tetrahydro-2-furanone；5-(N,N-dimethyl-4-aminobenzyl)-dihydrofuran-2-one；5-(N,N-dimethyl-4-aminobenzyl)dihydrofuran-2-one；5-[[4-(Dimethylamino)phenyl]methyl]oxolan-2-one
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: VCOJMKIRDJTXJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-二甲氨基苯酚 在 caesium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 2,2,2-三氟乙醇 为溶剂， 反应 22.0h， 生成 5-((N,N-dimethyl-4-aminophenyl)metyhyl)-2,3,4,5-tetrahydro-2-furanone
  参考文献：
  名称：

  Aryl Imidazylates and Aryl Sulfates As Electrophiles in Metal-Free ArS_N1 Reactions

  摘要：

  Some oxygen-bonded substituents were investigated as leaving groups in photoinduced ArSN1 reactions. Irradiation of aryl imidazylates and of the corresponding imidazolium salts mainly caused homolysis of the ArO-S bond. However, previously unexplored trifluoroethoxy aryl sulfates were found to undergo efficient metal-free arylation. The sulfates were conveniently generated in situ by dissolving the corresponding imidazolium salts in basic 2,2,2-trifluoroethanol.

  DOI：

  10.1021/jo502172c

文献信息

• Photoinduced, Ionic Meerwein Arylation of Olefins
  作者：Mariella Mella、Paolo Coppo、Benedetta Guizzardi、Maurizio Fagnoni、Mauro Freccero、Angelo Albini

  DOI：10.1021/jo010469s

  日期：2001.9.1

  sterochemistry of the addition across the alkene are best understood with a phenonium ion structure for the adduct. The nucleophile entering in beta can be varied under conditions in which the adduct cation is trapped more efficiently than the starting phenyl cation. Thus, beta-methoxyalkylanilines are formed when the irradiation is carried out in methanol. beta-Iodoalkylanilines are obtained in acetonitrile

  在极性溶剂中辐照4-氯苯胺或其N，N-二甲基衍生物会生成相应的三线态苯基阳离子。这些被烯烃捕获，以中等至良好的产率产生芳基化产物。B3LYP计算表明，三线态阳离子以可忽略不计的活化能滑动到与乙烯的键合加合物上，而与水仅形成略微稳定的CT复合物（被选为代表性的sigma亲核试剂）。最终产物的结构取决于加合物阳离子与烯烃的优选路径。在芳基烯烃的情况下，它去质子化为二苯乙烯衍生物，而从2，3-二甲基-2-丁烯和烯丙基三甲基硅烷，通过消除γ中的电离基团获得烯丙基苯胺。在单和二取代的烯烃的情况下，阳离子加氯而不是消除氯，得到β-氯烷基苯胺。通过加合物的phen离子结构可以最好地理解整个烯烃的加成反应的区域和立体化学。在其中加合物阳离子比起始苯基阳离子更有效地被捕获的条件下，可以改变进入β的亲核试剂。因此，当在甲醇中进行照射时，形成β-甲氧基烷基苯胺。在含碘化物和未取代的烷基苯胺的乙腈中，在硼氢化钠的
• Benzyl (Phenyl) γ- and δ-lactones via Photoinduced Tandem Ar−C, C−O Bond Formation
  作者：Stefano Protti、Maurizio Fagnoni、Angelo Albini

  DOI：10.1021/ja0627287

  日期：2006.8.1

  A convenient metal-free procedure for the preparation of benzyl (phenyl) gamma- and delta-lactones is illustrated. This method is based on the photochemical generation of phenyl cations and their reaction with 3, 4, or 5-alkenoic acids. This leads to a phenyl- or benzyl-substituted lactone by tandem formation of an aryl-C and C-O bond. The intermediacy of a phenonium ion imparts a full regio- and stereoselectivity to the reaction.
• Smooth Synthesis of Aryl- and Alkylanilines by Photoheterolysis of Haloanilines in the Presence of Aromatics and Alkenes
  作者：Maurizio Fagnoni、Mariella Mella、Angelo Albini

  DOI：10.1021/ol990982g

  日期：1999.10.1

  [GRAPHICS]Irradiation of 4 chloro-N,N-dimethylaniline in acetonitrile in the presence of benzene and of various alkenes leads to heterolytic dehalogenation and trapping of the cation. 4-(Dimethylamino)biphenyl is formed in the first case, while with alkenes beta-chloroalkylanilines, stilbenes, or allylanilines are obtained depending on the alkene structure. 4-Fluoroaniline is similarly dehalogenated.
• <i>Solar</i>ylations via 4-Aminophenyl Cations
  作者：Valentina Dichiarante、Maurizio Fagnoni、Angelo Albini

  DOI：10.1021/jo902669j

  日期：2010.2.19

  The application of the photo-S(N)1 reaction on sonic 4-chloroanilines was explored under solar irradiation in view of obtaining a convenient metal-free arylation method. Several reactions previously carried out by UV irradiation, as well as some new ones, where either a new trap (alpha-methylstyrene) ora new halide (N,N-dimethyl-4-fluoroaniline) were adopted, were studied under these conditions and found to occur conveniently. Furthermore, at least in some cases the halide starting concentration could be raised up to 0.2 M, the excess trapping agent reduced from 20:1 to 2.5:1, and the solvent replaced by more environmentally friendly (co)solvents including water. Under these improved conditions, the photoarylation was carried out in a gram scale by merely exposing the solution to solar irradiation. This process has a low impact on the environment and can be considered a serious competitor of metal-catalyzed arylations.
• Aryl Imidazylates and Aryl Sulfates As Electrophiles in Metal-Free ArS_N1 Reactions
  作者：Hisham Qrareya、Stefano Protti、Maurizio Fagnoni

  DOI：10.1021/jo502172c

  日期：2014.12.5

  Some oxygen-bonded substituents were investigated as leaving groups in photoinduced ArSN1 reactions. Irradiation of aryl imidazylates and of the corresponding imidazolium salts mainly caused homolysis of the ArO-S bond. However, previously unexplored trifluoroethoxy aryl sulfates were found to undergo efficient metal-free arylation. The sulfates were conveniently generated in situ by dissolving the corresponding imidazolium salts in basic 2,2,2-trifluoroethanol.