4-phenylsulfonylcyclohexene | 141642-46-8

• 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: 4-phenylsulfonylcyclohexene
• 英文别名: 1-phenylsulfonylcyclohex-3-ene；Cyclohex-3-en-1-ylsulfonylbenzene
• CAS: 141642-46-8
• 化学式: C₁₂H₁₄O₂S
• 分子量: 222.308
• InChiKey: OHQVZLHDLFOBBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-phenylsulfonylcyclohexene 在 palladium on activated charcoal 正丁基锂 、 氢气 作用下， 以 甲醇 、 乙醚 、 正己烷 为溶剂， 生成 1-(苯磺酰基)环己烷-1-羧酸
  参考文献：
  名称：

  A structure–taste study of arylsulfonyl(cyclo)alkanecarboxylic acids

  摘要：

  A number of sweeteners contain a sulfonyl group. In our current search for new glucophores several new compounds 14 containing such group were obtained. A series of novel 1-phenylsulfonylcyklohexanecarboxylic acids and 2-arylsulfonylalkanecarboxylic acids was obtained and evaluated for their sweet taste quality. It has been found that methyl substituents are of the key importance for the activity of these compounds. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.056
• 作为产物：
  描述：

  trans-1-mesyloxy-4-phenylsulfonylcyclohexane 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 6.0h， 以79%的产率得到4-phenylsulfonylcyclohexene
  参考文献：
  名称：

  Jeffery, Stephen M.; Stirling, Charles J. M., Journal of the Chemical Society. Perkin transactions II, 1993, # 9, p. 1617 - 1624

  摘要：

  DOI：

文献信息

• Strain-induced mechanism change: the limit of strain tolerance in intramolecular nucleophilic substitution?
  作者：Stephen M. Jeffery、Stefan Niedoba、Charles J. M. Stirling

  DOI：10.1039/c39920000650

  日期：——

  The limit of strain energy differential for intramolecular nucleophilic substitution via a sulfonyl-stabilised carbanion to give cyclopropane analogues in hydroxylic solvents is around 160 kJ mol–1; above this level, concerted, albeit unactivated, 1,2-elimination is preferred.

  在羟基溶剂中通过磺酰基稳定的碳负离子进行分子内亲核取代以得到环丙烷类似物的应变能差的极限约为 160 kJ mol–1；高于该水平，优选1，2-消除，尽管未激活，但一致。
• US7262299B2
  申请人：——

  公开号：US7262299B2

  公开（公告）日：2007-08-28
• A structure–taste study of arylsulfonyl(cyclo)alkanecarboxylic acids
  作者：Violetta Lysiak、Aleksander Ratajczak、Agnieszka Mencel、Krystyna Jarzembek、Jaroslaw Polanski

  DOI：10.1016/j.bmc.2004.10.056

  日期：2005.2

  A number of sweeteners contain a sulfonyl group. In our current search for new glucophores several new compounds 14 containing such group were obtained. A series of novel 1-phenylsulfonylcyklohexanecarboxylic acids and 2-arylsulfonylalkanecarboxylic acids was obtained and evaluated for their sweet taste quality. It has been found that methyl substituents are of the key importance for the activity of these compounds. (C) 2004 Elsevier Ltd. All rights reserved.
• Jeffery, Stephen M.; Stirling, Charles J. M., Journal of the Chemical Society. Perkin transactions II, 1993, # 9, p. 1617 - 1624
  作者：Jeffery, Stephen M.、Stirling, Charles J. M.

  DOI：——

  日期：——