3-p-tolylsulphonyl-2-p-tolylthiopropene | 97479-48-6

• 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: 3-p-tolylsulphonyl-2-p-tolylthiopropene
• 英文别名: 1-methyl-4-[3-(4-methylphenyl)sulfonylprop-1-en-2-ylsulfanyl]benzene
• CAS: 97479-48-6
• 化学式: C₁₇H₁₈O₂S₂
• 分子量: 318.461
• InChiKey: NWHTUYPLBPKVPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-p-tolylsulphonyl-2-p-tolylthiopropene 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以45%的产率得到4,4′-(prop-2-ene-1,2-diyldisulfonyl)bis(methylbenzene)
  参考文献：
  名称：

  烯丙基砜与烯烃的自由基加成反应

  摘要：

  描述了分子间自由基反应，该反应涉及烯丙基砜的磺酰基和烯丙基片段通过烯烃的双键的形式加成。当烯丙基砜在2-位具有吸电子基团时，反应最成功。尽管吸电子取代基和给电子取代基都是有效的，但只有单取代的烯烃才能提供有用的加合物收率。

  DOI：

  10.1016/s0040-4020(97)00306-2
• 作为产物：
  描述：

  prop-2-yn-1-yl(p-tolyl)sulfane 在 双氧水 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 溶剂黄146 为溶剂， 反应 4.75h， 生成 3-p-tolylsulphonyl-2-p-tolylthiopropene
  参考文献：
  名称：

  Mass spectral rearrangements of 3-arylsulphonyl-2-arylthiopropenes andN-(4′-arylsulphonyl-2′-butynyl)-N-(4″-arylthio-2″-butynyl)anilines

  摘要：

  AbstractUnder electron impact the title compounds undergo skeletal rearrangement in addition to the anticipated modes of cleavage. The 3‐arylsulphonyl‐2‐arylthiopropenes readily eliminate sulphur dioxide. Other modes of fragmentation include rearrangement to a bisaryl sulphide moiety and sulphone‐sulphinate rearrangement. The formation of a bisaryl sulphide ion is analogous to the behaviour of the isomeric trans‐1‐arylsulphonyl‐2‐arylthiopropenes. N‐(4′‐Arylsulphonyl‐2′‐butynyl)‐N‐(4″‐arylthio‐2″‐butynyl) anilines do not undergo any of the skeletal rearrangements mentioned above, but display the concerted loss of the arylsulphonyl and arylthio moieties. Similar eliminations have been observed from the analogous bis‐sulphides and bis‐sulphones.

  DOI：

  10.1002/oms.1210200404

文献信息

• Aspects of the chemistry of 4-tributylstannyl-, 4-trimethylsilyl- and 2-phenylsulfinylallylstannanes
  作者：Simon V Mortlock、Eric J Thomas

  DOI：10.1016/s0040-4020(98)00183-5

  日期：1998.4

  stannanes 3 and 4 have been prepared by treatment of the allylic sulfones 6 and 7 with tributyltin hydride under free-radical conditions and shown to react under non-catalysed and Lewis acid promoted conditions with 4-nitrobenzaldehyde to give the anti- and syn-products 9/11 and 8/10, respectively, with reasonable levels of stereoselectivity. The 2-arylsulfinylpropenylstannanes 17 and 18 were also

  通过在自由基条件下用氢化三丁基锡处理烯丙基砜6和7，制备了4-三甲基甲硅烷基-和4-三丁基锡烷基丁-2-烯基（三丁基）锡烷酮3和4，并显示了在非催化和路易斯条件下反应。酸促进的条件与4-硝基苯甲醛，得到的抗-和SYN -products 9/11和8/10分别与立体选择性的合理的水平。也从砜15和16制备2-芳基亚磺酰基丙烯基锡烷17和18。，并发现它会发生立体选择性氯化钛（IV）促进与醛的反应。
• Smith, Thomas A. K.; Whitham, Gordon H., Journal of the Chemical Society. Perkin transactions I, 1989, # 2, p. 319 - 325
  作者：Smith, Thomas A. K.、Whitham, Gordon H.

  DOI：——

  日期：——
• SMITH, THOMAS A. K.;WHITHAM, GORDON H., J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N, C. 319-325
  作者：SMITH, THOMAS A. K.、WHITHAM, GORDON H.

  DOI：——

  日期：——
• Mass spectral rearrangements of 3-arylsulphonyl-2-arylthiopropenes andN-(4′-arylsulphonyl-2′-butynyl)-N-(4″-arylthio-2″-butynyl)anilines
  作者：P. E. Glaspy、R. A. Hancock、B. S. Thyagarajan

  DOI：10.1002/oms.1210200404

  日期：1985.4

  AbstractUnder electron impact the title compounds undergo skeletal rearrangement in addition to the anticipated modes of cleavage. The 3‐arylsulphonyl‐2‐arylthiopropenes readily eliminate sulphur dioxide. Other modes of fragmentation include rearrangement to a bisaryl sulphide moiety and sulphone‐sulphinate rearrangement. The formation of a bisaryl sulphide ion is analogous to the behaviour of the isomeric trans‐1‐arylsulphonyl‐2‐arylthiopropenes. N‐(4′‐Arylsulphonyl‐2′‐butynyl)‐N‐(4″‐arylthio‐2″‐butynyl) anilines do not undergo any of the skeletal rearrangements mentioned above, but display the concerted loss of the arylsulphonyl and arylthio moieties. Similar eliminations have been observed from the analogous bis‐sulphides and bis‐sulphones.
• Free radical addition reactions of allylic sulfones to alkenes
  作者：Iain W. Harvey、Eifion D. Phillips、Gordon H. Whitham

  DOI：10.1016/s0040-4020(97)00306-2

  日期：1997.5

  Intermolecular radical reactions involving formal addition of the sulfonyl and allyl fragments of an allylic sulfone across the double bond of an alkene are described. Reactions are most successful when the allylic sulfone has an electron withdrawing group at the 2-position. Only monosubstituted alkenes give useful yields of adducts, though both electron withdrawing and electron donating substituents

  描述了分子间自由基反应，该反应涉及烯丙基砜的磺酰基和烯丙基片段通过烯烃的双键的形式加成。当烯丙基砜在2-位具有吸电子基团时，反应最成功。尽管吸电子取代基和给电子取代基都是有效的，但只有单取代的烯烃才能提供有用的加合物收率。