3-(4-fluorophenylsulfanyl)-cyclohexanone | 36640-27-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(4-fluorophenylsulfanyl)-cyclohexanone
• 英文别名: 3-((4-fluorophenyl)thio)cyclohexan-1-one；3-(p-fluorophenylthio)cyclohexanone；3-[(4-Fluorophenyl)sulfanyl]cyclohexan-1-one；3-(4-fluorophenyl)sulfanylcyclohexan-1-one
• CAS: 36640-27-4
• 化学式: C₁₂H₁₃FOS
• 分子量: 224.299
• InChiKey: DPCOKKVCMIJZES-UHFFFAOYSA-N

物化性质

• 沸点：
  345.8±37.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 对氟苯硫酚 在 tetrafluoroboric acid 、 silica gel 作用下， 反应 0.17h， 以90%的产率得到3-(4-fluorophenylsulfanyl)-cyclohexanone
  参考文献：
  名称：

  氟硼酸作为一种新型，高效且可重复使用的非均相催化剂，吸附在硅胶（HBF 4 -SiO 2）上，用于硫杂-迈克尔加成α，β-不饱和羰基化合物

  摘要：

  已经发现，吸附在硅胶上的氟硼酸（HBF 4 -SiO 2）是一种新型的高效多相催化剂，可在无溶剂条件下将硫杂-迈克尔加成到α，β-不饱和羰基化合物上。在1,3-二芳基-2-丙烯酮的情况下，反应最好在MeOH中进行。thia-Michael加成的速率取决于α，β-不饱和羰基底物的β-碳以及周围硫醇部分的位阻，并被用于在两个烯酮之间的分子间竞争中选择性的thia-Michael加成。常见的硫醇和两个芳基/烷基硫醇之间的一个常见的烯酮 该方法可用于一锅合成2,3-二氢-1,5-苯并噻氮ze类化合物。

  DOI：

  10.1016/j.tetlet.2008.04.144

文献信息

• Fluoroboric acid adsorbed on silica-gel (HBF4–SiO2) as a new, highly efficient and reusable heterogeneous catalyst for thia-Michael addition to α,β-unsaturated carbonyl compounds
  作者：Gaurav Sharma、Raj Kumar、Asit K. Chakraborti

  DOI：10.1016/j.tetlet.2008.04.144

  日期：2008.6

  found to be a new and highly efficient heterogeneous catalyst for thia-Michael addition to α,β-unsaturated carbonyl compounds under solvent-free conditions. In the case of 1,3-diaryl-2-propenones, the reactions are best carried out in MeOH. The rate of thia-Michael addition was dependent on the steric hindrance at the β-carbon of the α,β-unsaturated carbonyl substrate as well as surrounding the thiol

  已经发现，吸附在硅胶上的氟硼酸（HBF 4 -SiO 2）是一种新型的高效多相催化剂，可在无溶剂条件下将硫杂-迈克尔加成到α，β-不饱和羰基化合物上。在1,3-二芳基-2-丙烯酮的情况下，反应最好在MeOH中进行。thia-Michael加成的速率取决于α，β-不饱和羰基底物的β-碳以及周围硫醇部分的位阻，并被用于在两个烯酮之间的分子间竞争中选择性的thia-Michael加成。常见的硫醇和两个芳基/烷基硫醇之间的一个常见的烯酮 该方法可用于一锅合成2,3-二氢-1,5-苯并噻氮ze类化合物。
• 10.1039/d4ob00734d
  作者：Wu, Run、Xu, Haojian、Zhou, Haiping、Yu, Pingbing、Wen, Zhaoyue、Chen, Wei

  DOI：10.1039/d4ob00734d

  日期：——

  A stable and practical electrochemical method was developed to promote the thio-Michael addition of N-substituted maleimides to various thiols in an aqueous medium. This protocol was found to be excellent in terms of facile scale-up, oxidant- and catalyst-free conditions, broad substrate scopes, good functional group tolerance, and easily available substrates. Notably, a plausible reaction mechanism

  开发了一种稳定且实用的电化学方法来促进N-取代的马来酰亚胺在水介质中与各种硫醇发生硫代迈克尔加成。该方案在易于放大、无氧化剂和催化剂条件、广泛的底物范围、良好的官能团耐受性和易于获得的底物方面具有优异的性能。值得注意的是，一系列对照实验和CV研究的结果得出了一个合理的反应机制，这表明自由基途径可能会加速恒电流下的硫代迈克尔加成。
• Mild Hydrosulfenylation of Olefins under Neutral Conditions Using a Defined NHC-Ligated Iron–Sulfur Catalyst
  作者：Isabel Alt、Philipp Rohse、Bernd Plietker

  DOI：10.1021/cs4009336

  日期：2013.12.6

  A defined NHC-Fe-S complex proved to be an efficient catalyst for the selective hydrosulfenylation of alpha/beta-unsaturated ketones or vinylnitriles. A wide range of different aliphatic thiols were transferred in this atom-economic reaction into the corresponding thioethers. Mild reaction conditions, equimolar amounts of substrates, low catalyst loadings, and mild reaction conditions are characteristic for this transformation.
• WO2006/79480
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.