4-(p-tolylthio)octan-2-one | 1224975-67-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(p-tolylthio)octan-2-one
• CAS: 1224975-67-0
• 化学式: C₁₅H₂₂OS
• 分子量: 250.405
• InChiKey: FWVHSPLOFARPIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3-辛烯-2-酮 、 对甲苯二硫醚 在 rongalite 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以93%的产率得到4-(p-tolylthio)octan-2-one
  参考文献：
  名称：

  Rongalite® and base-promoted cleavage of disulfides and subsequent Michael addition to α,β-unsaturated ketones/esters: an odorless synthesis of β-sulfido carbonyl compounds

  摘要：

  A highly practical method to access beta-sulfido carbonyl compounds was developed, which could be conducted without any expensive reagent, special apparatus/technique, and no requirement of metal catalysts. beta-Sulfido carbonyl compounds were formed at room temperature, in short time and with high chemoselectivity in good to excellent yields. A plausible mechanism for the role of Rongalite (R), as a promoter for the cleavage of disuffides generating thiolate anions that then undergo facile thia-Michael addition to alpha,beta-unsaturated ketones and esters is proposed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.02.001

文献信息

• Aliphatic polyketones via cross-metathesis polymerization: Synthesis and post-polymerization modification
  作者：Fu-Rong Zeng、Jing Xu、Qi Xiong、Kai-Xuan Qin、Wei-Jun Xu、Yue-Xin Wang、Zan-Jiao Liu、Zi-Long Li、Zi-Chen Li

  DOI：10.1016/j.polymer.2019.121936

  日期：2019.12

  α-olefin and vinyl ketone units of monomer 2. Optimization of polymerization condition was conducted to generate unsaturated polyketone P0 (Mn,GPC = 14 kDa), and the results of kinetic study verified high efficiency and structural integrity of this system. Furthermore, post-polymerization modification of P0 by using thiol-Michael chemistry furnished functional polyketones P1–P6, and full conversion of the

  聚烯烃由于其大量消耗和广泛应用而引起了相当大的关注。在这项研究中，交叉复分解聚合（CMP）被证明是合成脂肪族聚酮的一种有效而可行的方法。合成路线收率高，条件温和，操作简便。CMP的成功取决于α-烯烃和单体2的乙烯基酮单元之间的高复分解趋势。进行了聚合条件的优化以生成不饱和聚酮P0（M n，GPC  = 14 kDa），动力学研究的结果证实了该系统的高效率和结构完整性。此外，P0的聚合后修饰通过使用硫醇-迈克尔化学提供的功能性聚酮P1 - P6，在每种情况下均观察到P0内部乙烯基酮基团的完全转化。原始的和功能性的聚酮P0 - P6实际上可溶于大多数常见的有机溶剂。特别地，还通过这种方式获得了疏水和荧光聚酮（P5和P6）。因此，这种合成策略显示出有希望的未来，并例证了合成多种功能性聚酮的巨大潜力。
• Rongalite® and base-promoted cleavage of disulfides and subsequent Michael addition to α,β-unsaturated ketones/esters: an odorless synthesis of β-sulfido carbonyl compounds
  作者：Wenxue Guo、Guangshu Lv、Jiuxi Chen、Wenxia Gao、Jinchang Ding、Huayue Wu

  DOI：10.1016/j.tet.2010.02.001

  日期：2010.3

  A highly practical method to access beta-sulfido carbonyl compounds was developed, which could be conducted without any expensive reagent, special apparatus/technique, and no requirement of metal catalysts. beta-Sulfido carbonyl compounds were formed at room temperature, in short time and with high chemoselectivity in good to excellent yields. A plausible mechanism for the role of Rongalite (R), as a promoter for the cleavage of disuffides generating thiolate anions that then undergo facile thia-Michael addition to alpha,beta-unsaturated ketones and esters is proposed. (C) 2010 Elsevier Ltd. All rights reserved.