3-(2-hydroxyethylsulfanyl)cyclohexanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-hydroxyethylsulfanyl)cyclohexanone
• 英文别名: 3-(2-hydroxyethylthio)cyclohexanone；3-(2-Hydroxyethylsulfanyl)cyclohexan-1-one
• 化学式: C₈H₁₄O₂S
• 分子量: 174.264
• InChiKey: LCEIXQQPXKMFGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 2-巯基乙醇 在 C₃₂H₂₄Cu₂F₁₂N₂O₁₄S₄ 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 144.0h， 以44%的产率得到3-(2-hydroxyethylsulfanyl)cyclohexanone
  参考文献：
  名称：

  联苯基配体的合成：在铜介导的化学选择性迈克尔反应中的应用

  摘要：

  摘要 在铜介导的迈克尔反应中合成并筛选了一种基于联苯的配体。该催化剂体系与碳或硫亲核试剂作为迈克尔供体和环己烯酮或查耳酮作为受体在温和和中性反应条件下以化学选择性方式很好地工作。图形概要

  DOI：

  10.1080/00397911.2014.946996

文献信息

• L-Proline Catalyzed Michael Additions of Thiophenols to α,β-Unsaturated Compounds, Particularly α-Enones, in the Ionic Liquid [bmim]PF6
  作者：Peter Kotrusz、Stefan Toma

  DOI：10.3390/11020197

  日期：——

  L-proline catalyzed additions of 13 different thiols to 11 different alpha-enone Michael acceptors in [bmim] PF(6 )are reported. Reasonable to high yields of the reaction products were isolated in most cases.

  据报道，L-脯氨酸催化了 [bmim] PF(6) 中 13 种不同硫醇与 11 种不同 α-烯酮迈克尔受体的添加。在大多数情况下分离出合理到高产率的反应产物。
• Catalytic carbon–sulfur bond formation by amphoteric vanadyl triflate: exploring with thia-Michael addition, thioacetalization, and transthioacetalization reactions
  作者：Chien-Tien Chen、Yow-Dzer Lin、Cheng-Yuan Liu

  DOI：10.1016/j.tet.2009.10.012

  日期：2009.12

  A series of thiols have been examined as protic nucleophiles for Michael-type additions to alpha,beta-unsaturated carbonyls as well as double nucleophilic condensations with aldehydes, ketones, and acetals catalyzed by amphoteric, water-tolerant vanadyl triflate under mild and neutral conditions. The newly developed C-S bond formation protocols were carried out smoothly in good to high yields in a highly chemoselective manner. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.
• Synthesis of Biphenyl-Based Ligand: Application in Copper-Mediated Chemoselective Michael Reaction
  作者：M. Shyam Sundar、Ashutosh V. Bedekar

  DOI：10.1080/00397911.2014.946996

  日期：2014.12.17

  Abstract A biphenyl-based ligand attached was synthesized and screened in copper-mediated Michael reaction. The catalyst system works well with carbon or sulfur nucleophiles as Michael donors and cyclohexenone or chalcones as the acceptors under mild and neutral reaction conditions in a chemoselective manner. GRAPHICAL ABSTRACT

  摘要 在铜介导的迈克尔反应中合成并筛选了一种基于联苯的配体。该催化剂体系与碳或硫亲核试剂作为迈克尔供体和环己烯酮或查耳酮作为受体在温和和中性反应条件下以化学选择性方式很好地工作。图形概要