p-tolyl 9-fluorenyl sulfone | 102001-66-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: p-tolyl 9-fluorenyl sulfone
• 英文别名: fluoren-9-yl-p-tolyl sulfone；Fluoren-9-yl-p-tolyl-sulfon；9-p-Tolylsulfon-fluoren；--sulfon；9-<4-Methyl-phenyl-sulfonyl>-fluoren；9-p-Tolylsulfon-fluoren；9-(4-methylphenyl)sulfonyl-9H-fluorene
• CAS: 102001-66-1
• 化学式: C₂₀H₁₆O₂S
• 分子量: 320.412
• InChiKey: PTVXAANTOKVUAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  p-tolyl 9-fluorenyl sulfone 在 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (9-Hydroxymethyl-fluoren-9-yl)-(p-tolyl)-sulfon
  参考文献：
  名称：

  芴的脂肪族化学：第 IX 部分。一些双功能衍生物

  摘要：

  菲-9-羧酸甲酯、菲-9,10-二甲酸二甲酯和N,N-二甲基菲-9-甲酸甲酯已通过一种新途径直接由芴制备。邻村...

  DOI：

  10.1139/v64-215
• 作为产物：
  描述：

  potassium thiotosylate 在 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 4.5h， 生成 p-tolyl 9-fluorenyl sulfone
  参考文献：
  名称：

  9-Fluorenyl 9-(p-tolylsulfonyl)-9-fluorenyl disulfide: the unexpected product of the reaction of 9-bromofluorene and potassium p-toluenethiosulfonate and the mechanism of its formation

  摘要：

  Reaction of potassium p-toluenethiosulfonate with 9-bromofluorene leads, not to the expected 9-fluorenyl p-toluenethiosulfonate (3), but rather to a product shown to be 9-fluorenyl 9-(p-tolylsulfonyl)-9-fluorenyl disulfide (7, R = 9-fluorenyl) (eq 11). This disulfide of unusual structure is shown to arise as a result of the following reaction sequence: (a) initial formation of 3; (b) a facile elimination of 3 (due to the acidity of the 9-H), forming p-toluenesulfinic acid and 9-thiofluorenone (4); (c) addition of p-CH3C6HSO2- to 4 to give alpha-sulfonyl thiolate ion 16; and (d) reaction of 16 with remaining 3 (in a rapid displacement at the dicoordinate sulfur) to give 7 plus regeneration of p-CH3C6H4SO2-.

  DOI：

  10.1021/jo00021a036

文献信息

• Copper-Catalyzed Nitrogen Loss of Sulfonylhydrazones: A Reductive Strategy for the Synthesis of Sulfones from Carbonyl Compounds
  作者：Xing-Wen Feng、Jian Wang、Ji Zhang、Jing Yang、Na Wang、Xiao-Qi Yu

  DOI：10.1021/ol101955x

  日期：2010.10.1

  An efficient method for the synthesis of sulfones via nitrogen loss of sulfonyl hydrazones is described. The reaction was performed in the presence of simple copper salt and base by utilization of sulfonyl hydrazones, which were easily prepared from carbonyl compounds. A wide variety of aryl and alkyl sulfones were obtained in moderate to good yields.

  描述了一种通过磺酰基的氮损失合成砜的有效方法。该反应在简单的铜盐和碱的存在下通过利用磺酰基来进行，所述磺酰基易于从羰基化合物制备。以中等至良好的产率获得了各种各样的芳基和烷基砜。
• ALIPHATIC CHEMISTRY OF FLUORENE:PART IV. PREPARATION AND ALKYLATION OF SOME SULPHIDES AND SULPHONES
  作者：P. M. G. Bavin

  DOI：10.1139/v60-129

  日期：1960.6.1

  The preparations are described of some 9-fluorenyl sulphides which have been oxidized with peracetic acid to the corresponding sulphones.9-Fluorenyl p-tolyl sulphone has been alkylated with a range of alkyl halides; other sulphones, including 2-nitro-9-fluorenyl p-tolyl sulphone, have been methylated.Methyl fluorene-9-carboxylate anion was reduced by p-toluenesulphonyl chloride to dimethyl 9,9′-difluorenyl-9

  描述了一些 9-芴基硫化物的制备方法，这些硫化物已被过乙酸氧化成相应的砜。9-芴基对甲苯基砜已被一系列烷基卤化物烷基化；其他砜，包括 2-硝基-9-芴基对甲苯基砜，已被甲基化。芴-9-羧酸甲酯阴离子被对甲苯磺酰氯还原为 9,9'-二芴基-9,9'-二甲酸二甲酯。
• Adickes, Journal fur praktische Chemie (Leipzig 1954), 1936, vol. <2> 145, p. 235,242
  作者：Adickes

  DOI：——

  日期：——
• XCIV.—Influence of poles and polar linkings on the course pursued by elimination reactions. Part VIII. The methylenic and paraffinic degradations of sulphones
  作者：Christopher Kelk Ingold、Joe Arthur Jessop

  DOI：10.1039/jr9300000708

  日期：——