3-n-propylthio-1-cyclohexanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-n-propylthio-1-cyclohexanone
• 英文别名: 3-Propylsulfanylcyclohexan-1-one
• 化学式: C₉H₁₆OS
• 分子量: 172.291
• InChiKey: UXXVFXBGZWDXPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 丙烷-1-硫醇 在 ammonium cerium(IV) nitrate air 作用下， 反应 0.67h， 以95%的产率得到3-n-propylthio-1-cyclohexanone
  参考文献：
  名称：

  硝酸铈铵（CAN）作为绿色高效的助催化剂，用于将硫醇和苯硒酚加成到α，β-不饱和酮上的1,4-

  摘要：

  描述了一种温和而有效的方法，该方法使用催化量的CAN以优异的产品收率将硫醇和苯硒酚的1,4-加成成各种α，β-不饱和酮。这种廉价，无毒且容易获得的催化硝酸铈（IV）铵体系可在无溶剂条件下有效催化硫醇衍生物与各种α，β-不饱和酮之间的共轭加成反应。提出了一种可能的机制，即CAN在自由基链加成反应中作为促进剂以及在共轭加成过程中的催化作用。

  DOI：

  10.1016/j.tet.2006.12.018

文献信息

• Ceric ammonium nitrate (CAN) as a green and highly efficient promoter for the 1,4-addition of thiols and benzeneselenol to α,β-unsaturated ketones
  作者：Cheng-Ming Chu、Shijay Gao、M.N.V. Sastry、Chun-Wei Kuo、Chaowei Lu、Ju-Tsung Liu、Ching-Fa Yao

  DOI：10.1016/j.tet.2006.12.018

  日期：2007.2

  efficient process for the 1,4-addition of thiols and benzeneselenols to various α,β-unsaturated ketones using a catalytic amount of CAN with excellent product yields is described. This inexpensive, nontoxic, and readily available catalytic ceric(IV) ammonium nitrate system efficiently catalyzes conjugate addition reactions between thiol derivatives and various α,β-unsaturated ketones under solvent-free conditions

  描述了一种温和而有效的方法，该方法使用催化量的CAN以优异的产品收率将硫醇和苯硒酚的1,4-加成成各种α，β-不饱和酮。这种廉价，无毒且容易获得的催化硝酸铈（IV）铵体系可在无溶剂条件下有效催化硫醇衍生物与各种α，β-不饱和酮之间的共轭加成反应。提出了一种可能的机制，即CAN在自由基链加成反应中作为促进剂以及在共轭加成过程中的催化作用。
• The iron(III) chloride-mediated 1,4-addition of mercaptans to α,β-unsaturated ketones and esters under solvent free conditions
  作者：Cheng-Ming Chu、Wan-Ju Huang、Chaowei Lu、Pohsi Wu、Ju-Tsung Liu、Ching-Fa Yao

  DOI：10.1016/j.tetlet.2006.07.151

  日期：2006.10

  The 1,4-addition of various thiols to alpha,beta-unsaturated ketones was completed rapidly in the presence of a catalytic amount (2-3 mol %) of anhydrous iron(III) chloride under solvent free conditions and an air atmosphere. Anhydrous iron(III) chloride is more active than that of other ferric salts. With more reactive and/or less steric reagents (1a-c and/or 2a-2c), expeditious conditions (short reaction times at room temperature) could be employed. With less reactive and/or steric reagents (1d-g and/or 2d-e), a slight increase in reaction time was required, but high yields were obtained. The FeCl3 catalyst causes preferential interactions with alpha,beta-unsaturated ketones present in the reaction. (c) 2006 Published by Elsevier Ltd.
• Organic reaction in water. Part 2: Michael addition in water without phase transfer agents
  作者：Flavia Martins da Silva、Adriana Kniaseff Gomes、Joel Jones, Jr.

  DOI：10.1139/cjc-77-5-6-624

  日期：——

  The Michael additions of dicarbonyl compounds, nitroalkanes, and thiols to 2-cyclohexen-1-one can be accomplished in water without phase transfer agents. The reaction is extremely sensitive to the pH of the reaction media, and therefore, the methodology can be optimized with the control of this variable. The best pH depends on the used nucleophile.
• Pronounced Catalytic Effect of a Micellar Solution of Sodium Dodecyl Sulfate (SDS) on the Efficient C-S Bond Formation<i>via</i>an Odorless Thia-Michael Addition Reaction through the<i>in situ</i>Generation of<i>S</i>-Alkylisothiouronium Salts
  作者：Habib Firouzabadi、Nasser Iranpoor、Mohammad Abbasi

  DOI：10.1002/adsc.200800690

  日期：2009.3

  Abstractmagnified imageA pronounced catalytic effect of sodium dodecyl sulfate (SDS) was observed on thein situproduction ofS‐alkylisothiouronium saltsviathe reaction of primary, allyl and benzyl halides with thiourea in SDS droplets .Hydrolysis of the generatedS‐alkylisothiouronium salts in the palisade layer of the droplets produces the corresponding thiol moieties which are immediately added to the electron‐deficient olefins that are present in the micellar core to produce the thia‐Michael adducts. The entire route is an almost odorless process. The yields of the products are good to excellent and the method is applicable to large‐scale operation without any problem.
• 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.