2,3,5,6-tetramethylbenzenesulfonyl fluoride | 63316-23-4

• 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: 2,3,5,6-tetramethylbenzenesulfonyl fluoride
• 英文别名: 2,3,5,6-Tetramethylbenzenesulfonyl fluoride
• CAS: 63316-23-4
• 化学式: C₁₀H₁₃FO₂S
• 分子量: 216.276
• InChiKey: OSALMMDMQBXQLX-UHFFFAOYSA-N

物化性质

• 沸点：
  305.4±42.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3,5,6-tetramethylbenzenesulfonyl fluoride 在 p-(trifluoromethyl)phenyl(difluoro)-λ3-bromane 作用下， 以 苯 为溶剂， 反应 2.0h， 以85%的产率得到N-(2,3,5,6-tetramethylphenyl)sulfamoyl fluoride
  参考文献：
  名称：

  Ochiai, Masahito; Okada, Takuya; Tada, Norihiro, Journal of the American Chemical Society, 2009, vol. 131, p. 8392 - 8393

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,4,5-四甲苯 在 氟磺酸 作用下， 反应 3.0h， 以90%的产率得到2,3,5,6-tetramethylbenzenesulfonyl fluoride
  参考文献：
  名称：

  Arapov, O. V.; Rudenko, A. P.; Zarubin, M. Ya., Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 1, p. 152 - 163

  摘要：

  DOI：

文献信息

• Reactions of Vinyl Type Carbocations Generated in Fluorosulfonic Acid with Benzene Derivatives. New Synthesis of Alkyl 3,3-Diarylpropenoates
  作者：P. Yu. Savechenkov、A. P. Rudenko、A. V. Vasil'ev、G. K. Fukin

  DOI：10.1007/s11178-005-0340-6

  日期：2005.9

  Vinyl type carbocations ArC+=CHX [X = CO2H, CO2Alk, C≡N, P(O)(OAlk)2] generated from alkyl 3-arylpropynoates and related compounds in fluorosulfonic acid at −75 to −20°C react with various benzene derivatives, following the mechanism of electrophilic substitution of hydrogen. A new procedure for the synthesis of alkyl 3,3-diarylpropenoates having various substituents in the aryl fragments has been developed on the basis of protonation of the triple bond in alkyl 3-arylpropynoates.

  由烷基3-芳基丙炔酸酯及相关化合物在氟磺酸中于−75至−20°C生成的乙烯基类型的碳正离子ArC+=CHX [X = CO2H, CO2Alk, C≡N, P(O)(OAlk)2]，与各种苯衍生物反应，遵循氢的电亲体取代机制。基于烷基3-芳基丙炔酸酯中三键的质子化，开发了一种合成具有不同芳基片段取代基的烷基3,3-二芳基丙烯酸酯的新方法。
• Rudenko, A. P., Russian Journal of Organic Chemistry, 1994, vol. 30, # 12, p. 1946 - 1980
  作者：Rudenko, A. P.

  DOI：——

  日期：——
• Dual Reactivity of the Formyl Cation as an Electrophile and a Broensted Acid in Superacids
  作者：Matsuo Tanaka、Masahiro Fujiwara、Hisanori Ando

  DOI：10.1021/jo00117a041

  日期：1995.6

  The nature of the formyl cation in the Gattermann-Koch formylation was studied by comparing the formylation with the acetylation and sulfonation in CF3SO3H-SbF5 and FSO3H-SbF5, respectively. The results of the kinetic studies in CF3SO3H-SbF5 showed that the formyl cation has dual reactivity as an electrophile and as a Bronsted acid. Upon comparing the formylation with the sulfonation in FSO3H-SbF5, it was found that the protonated aromatic compounds also act as Bronsted acids to produce formyl cations. Therefore, the formylation has a priority over other typical electrophilic substitutions under conditions where most of aromatic compounds are protonated because the formyl cation is reproduced close to the aromatic compounds by the protonation of CO with not only superacids but also protonated aromatic compounds.
• Rudenko; Salfetnikova; Vasil'ev, Russian Journal of Organic Chemistry, 1996, vol. 32, # 10, p. 1447 - 1470
  作者：Rudenko、Salfetnikova、Vasil'ev

  DOI：——

  日期：——
• Reactions of acetylene ketones in superacids
  作者：S. A. Aristov、A. V. Vasil’ev、G. K. Fukin、A. P. Rudenko

  DOI：10.1134/s1070428007050107

  日期：2007.5

  Vinyl type cations ArC+=CHCOR generated from acetylene ketones ArC CCOR in superacids HSO3F and CF3SO3H react with diverse benzene derivatives to form alkenylation products, E-/Z-isomers of diarylpropenone structures Ar(Ar')C=CHCOR. The alkenylation of aromatic compounds with acetylene ketones in superacids occurs with the primary syn-addition of a hydrogen and an aryl residue to the acetylene bond followed by transformation of the product into anti-isomer under the conditions of the reaction.