4-(2-pyridinesulfanyl)butan-2-one | 134257-68-4

• 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-(2-pyridinesulfanyl)butan-2-one
• 英文别名: 4-Pyridin-2-ylsulfanylbutan-2-one
• CAS: 134257-68-4
• 化学式: C₉H₁₁NOS
• mdl: MFCD02315234
• 分子量: 181.258
• InChiKey: LJSNDSCRXIWWRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  55.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-巯基吡啶 、 丁烯酮 在 SiliaBond thiourea 作用下， 反应 0.25h， 以75%的产率得到4-(2-pyridinesulfanyl)butan-2-one
  参考文献：
  名称：

  Silicon-based thiourea-mediated and microwave-assisted thio-Michael addition under solvent-free reaction conditions

  摘要：

  摘要：基于硅的硫脲（SiliaBond® Thiourea）（Si-THU）作为一种非均相催化剂，已应用于在55-60°C的无溶剂条件下通过巯基与α，β-不饱和羰基化合物的迈克尔加成实现高选择性的C-S键形成。在优化条件下，硫迈克尔加成产物以优异的产率获得。这种方法涉及无金属和金属清除剂催化剂，被发现是硫迈克尔加成反应的一种替代方法。

  DOI：

  10.2478/s11696-011-0052-z

文献信息

• N-Heterocyclic Carbene Catalyzed Carba-, Sulfa-, and Phospha-Michael Additions with NHC·CO₂ Adducts as Precatalysts
  作者：Morgan Hans、Lionel Delaude、Jean Rodriguez、Yoann Coquerel

  DOI：10.1021/jo500108a

  日期：2014.3.21

  N-heterocyclic carbene catalyzed Michael additions have been revisited with 1,3-dialkyl- or 1,3-diarylimidazol(in)ium-2-carboxylates, that is, NHC center dot CO2 adducts, as the source of the free NHC catalysts in solution. Using these precatalysts, a number of efficient carba-, sulfa-, and phospha-Michael additions were achieved very conveniently, without the need for an external strong base to generate the NHC by deprotonation of an azolium salt. To further expand the scope of the procedure, some NHC-catalyzed sulfa-Michael/aldol organocascades were also investigated.
• Electrocatalytic addition of thiols to activated olefins
  作者：M. E. Niyazymbetov、L. D. Konyushkin、Z. I. Niyazymbetova、V. P. Litvinov、V. A. Petrosyan

  DOI：10.1007/bf00959684

  日期：1991.1
• Silicon-based thiourea-mediated and microwave-assisted thio-Michael addition under solvent-free reaction conditions
  作者：Kamalakannan Prabakaran、Machindra Gund、Tae Kim、Euh Jeong、Chae Oh、Fazlur-Rahman Nawaz Khan、Jong Jin

  DOI：10.2478/s11696-011-0052-z

  日期：2011.1.1

  Silicon-based thiourea (SiliaBond® Thiourea) (Si-THU), a heterogeneous catalyst, has been applied to the highly selective C-S bond formation via Michael addition of thiols to α,β-unsaturated carbonyl compounds under solvent-free conditions at 55–60°C. The thio-Michael addition products were obtained in an excellent yield under optimised conditions. This methodology involving a metal-free as well as a metal scavenger catalyst has been found to be an alternative method for the thio-Michael addition reaction.

  摘要：基于硅的硫脲（SiliaBond® Thiourea）（Si-THU）作为一种非均相催化剂，已应用于在55-60°C的无溶剂条件下通过巯基与α，β-不饱和羰基化合物的迈克尔加成实现高选择性的C-S键形成。在优化条件下，硫迈克尔加成产物以优异的产率获得。这种方法涉及无金属和金属清除剂催化剂，被发现是硫迈克尔加成反应的一种替代方法。